key west weekend trip

2 days in Key West Itinerary: Perfect Weekend Trip

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Located in the state of Florida is Key West which is the southernmost point in the United States. If you are looking for a weekend of watersports, sandy beaches, and historic sites, then this 2 days in Key West itinerary is perfect for you!

2 days in Key West Itinerary: How to spend the perfect weekend

Disclosure: This post contains affiliate links. If you click one of them, we may receive a small commission at no extra cost to you.

Planning a trip to Key West: Travel Tips

Here are some important travel tips and information about Key West

• International Airport: Key West International Airport (EYW)
• Currency : USD
• Where to stay : Book hotels here 
• Recommended tours : Town trolley Tours ,  Sunset Cruise , Snorkeling & Dolphin watching
• Day trips from Key West: Miami, Florida Keys Road trip, Dry Tortugas National Park, Everglades National Park, Biscayne National Park (more options below)

2 day Key West Itinerary

• Day 1: Arrive in Key West. Explore the Historic District attractions, hang out at the Duval Street
• Day 2: Snorkel tour OR Snorkel & Dolphin watching, beach time, sunset cruise (Food & culture tour for non-water sports activity) 

Key West is a walkable city, and you can enrich your vacation by adding snorkeling, and sailing adventures. 

Getting to Key West Florida:

Key West is served by the Key West International Airport or EYW. You can arrive there via connections or direct flights from a host of Florida cities, the USA, and other parts of the world. The average flight duration from New York City to Key West is about 3.25 hours. 

From the airport, you can access ground transportation, including local shuttle buses and rental cars to get to your hotel or old town area. 

This 2 day Key West itinerary is also perfect if you are road tripping in Florida. Combine a trip to Miami and Key West and make it a Florida Keys itinerary with stops at tropical national and state parks. Miami to Key West is 3.50 hours (one way) by road, or you can also fly.  

Where to stay in Key West for 2 nights

For a short weekend trip to Key West Florida, we recommend staying at the old town or near it. The Old Town is also known as the Historic District, and from here one can easily walk to various sightseeing attractions, and find cafes and restaurants nearby. 

Recommendation for Key West Hotels 

• Truman Hotel: Truman Hotel is a boutique hotel located in the heart of Key West, and is one of their popular accommodation options. Attractions and cafes are within a 5 to 6 minute walk. The hotel also offers continental breakfast by poolside. Book your stay here
• Almond Tree Inn: This Key West hotel is located in the downtown area, and is within walking distance to key attractions such as the Hemingway Home, the Lighthouse, and museums. Although based in the heart of all the action in Key West, it is surprisingly quiet and welcoming. However, no kids are allowed at the property. Check availability and prices here
• Silver Palms Inn: Silver Palms Inn is also located in the downtown area and is about a 9-minute walk away from the city’s iconic attractions. However, this hotel allows children and also has a large outdoor pool. Check out photos, and availability here
• If you are looking for an apartment, then Truman @ Duval is a good one to consider. 

In the historic district and nearby, you can easily find vacation rentals, and modest hotels to fit your budget. Search for hotels for your Key West vacation here

Day 1 of 2 day Key West Itinerary: Explore the historic side of Key West, and hang out at the Duval Street in the evening 

Once you are at the Old Town and settled in, hop on the sightseeing Trolley to explore the major historical attractions in Key West.

Best way to see Key West in a day: We recommend the Old Town Trolley Tour with 12 stops , which is a perfect way to check off all the attractions on day one of your Key West Itinerary. 

You can grab your tickets here. It is valid for 1 day . In this convenient tour, you can hop on and hop off at about 12+ stops. 

There are other options for transportation and sightseeing in Key West, other than the trolley tours. You can use the free Duval Loop bus shuttle, or get on the Conch Tour Train Tour. 

Here is what you must explore on day one in Key West. 

Wander the Historic District

The Key West Historic District aka the Old Town of the City of Key West) is about 4000 acres and is filled with over 180 historic buildings. In the 1980s, it was expanded to include more areas such as Mallory Square. Today it is home to 2485 historic buildings. 

Spend some day strolling the lanes, and various quarters or admire the district from the comfort of your Trolley seat before getting down to explore.

Key West Cemetery

At the old town, pay a visit to the Key West Cemetery. This cemetery dates back to 1847 and about 100,000 are buried here. There are free walking tours that you can go on to learn about its history and hear all the quirky stories. Here is a  self guided tour to consider. 

Truman Little White House

Truman Little White House is another stop at the Old town. It is located at the Truman Annex, which was the former winter residence of US President Harry Truman. 

It is a presidential museum in Florida, and you will find that many pieces of furniture are still in place. You can grab tickets here for the house/museum tour

Mallory Square and the Historic Seaport

A short walk from the Truman House is the Mallory Square and the Historic Seaport . 

Mallory Square is a lovely plaza located on the waterfront area in the historic Old Town, facing the Gulf of Mexico. The cruise ship port is adjacent to it.  

Stop here for soaking in water views, or rest and grab a bite to eat, before exploring the next set of attractions. 

From the Mallory Square, you can pick 2-3 sites to visit next. They are all located within walking distance from the waterfront. 

The Key West Aquarium

The Key West Aquarium is about a minute walk away. It is the only public aquarium in Key West, and is worth visiting!

Set aside about 45 minutes to an hour at the aquarium. Tickets start at $17 USD for adults, and you are allowed to explore the complex in a day (consecutive) day period. 

Ernest Hemingway Home

Ernest Hemingway lived in Key West for a while and Ernest Hemingway Home was his residence in the 1930s. The home is very well-maintained and showcases the way Hemingway lived there with original architecture and furnishings. 

The museum is open all days of the year, and tickets start at $14 USD for adults. One of the coolest things about this museum is that it has about 57 (and counting) cats, wandering everywhere in the complex.

Key West Lighthouse

From the Hemingway House, walk to the Key West Lighthouse for a nice snap and exploration. This lighthouse dates back to 1825 and was originally meant to assist ships to avoid the hazardous reefs. 

With a history of over 120 years, a visit to the museum (located on-site) is a must to understand the history of Key West and its surrounding areas. 

If you have time on your hands, climb 88 steps to reach the top of the tower for some amazing views.

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park is another spot worth exploring in Key West. It is a historical and a coastal area located at the southern tip of Key West (at the end of Southard Street on Truman Annex). The site is centered around the Civil War-era fort. 

The entrance fee to the park is $2.50 USD, or $7 for two with a vehicle. 

Key West Butterfly and Nature Conservatory

Also located at Duval Street is the Key West Butterfly and Nature Conservatory. This conservatory is home to over 60 different species of live butterflies from all over the world. 

The butterflies are kept inside climate-controlled, and glass-enclosed habitat. Tickets start at $10 to $13 USD. 

Other than butterflies, don’t forget to meet the cutest flamingos – Scarlet and Rhett. 

Southernmost Point of the Continental United States 

2 minute walk from the conservatory is the Southernmost Point of the Continental US, marked by an anchored concrete buoy. Don’t forget to snap a photo here!

Additional sightseeing attractions to consider : You can easily swap the recommendations above with these options, all located in the Old Town  – Key West Shipwreck Treasure Museum, Key West Historic Memorial Sculpture Garden, Mel Fisher Maritime Museum, and the Audubon House.

Finish the day at Duval Street

Duval Street is the heart of the Downtown area of Key West. It is known for its active nightlife, and here you will find awesome places to hang out and chill – from bars, restaurants, to nightclubs. 

Here are some restaurant recommendations for the evening, 

• Visit the historic Sloppy Joe’s, which was a personal favorite of Ernest Hemingway. Enjoy cuisine, and live music
• Sit down at Red Shoe Island Bistro , and try their Key Lime pie and Pork tenderloins
• Head to Martin’s for a European dinner experience 
• For delicious seafood, head to Matt’s Stock Island Kitchen in Key West

Day 2 of Key West Itinerary 2 days: Go snorkeling, dolphin watching, beach time and set sailing on a sunset cruise  

For day 2 in Key West, indulge in water sports of your choice, followed by beach time and a sunset cruise to finish the day. 

From snorkeling, jet skiing to dolphin watching, there are a ton of adventurous things to do in Key West. 

We have shortlisted these tours from GetYourGuide (our trusted tour provider which we have been using for the past 5 + years or so). You can easily book them online. If you prefer booking on the spot (when in Key West) then Fury Water Adventures is a good option to consider.

We have also included non water sports activities below, so keep reading!

Snorkeling with breakfast and Mimosas (3 hours)

This 3 hour snorkeling tour comes with a breakfast option. You have to arrive at the port, and then join the cruise. On broad you will enjoy epic views of the coastline and snack on a delicious, light breakfast plus mimosas.

In this highly recommended tour, you get to enjoy some of Key West’s 110 species of coral and 500 species of tropical fish.

At the snorkel site, your guide will provide all the necessary gear and safety briefing. Your instructor will lead you to the impressive coral reef and snorkel as you go in search of colorful marine life. 

You can book your 3 hour tour with breakfast here . For snorkeling do remember to bring your swimwear and a towel. 

Dolphin and Snorkel Tour (3 hours)

Here is another alternative where you can combine a dolphin watching and a snorkeling tour too .

In this 3 hour tour, you are taken on a fast catamaran to see Key West dolphins. After that, you will be guided to the Key West wildlife refuge to snorkel in the shallow backcountry waters. 

The tour guide will be leading the way, so if snorkeling is new to you, no worries as you are in safe hands. You can book your tour here (3 hours)

Other tours: 

• Jet ski:  You may add a 90 minute jet ski adventure . This is a 28-mile tour in which an expert guides through the Key West backcountry, passing remote islands, Mallory Square, and the southernmost point in the US. 
• Full day adventure: For a full day of water sports, opt for this 6.50 hour tour. It takes care of your breakfast, lunch and takes you snorkeling, parasailing, and jet skiing too! Learn more about it here

Beaches in Key West 

If you are not into watersports, consider spending time at the beach, and joining a food and cultural tour. Popular beaches in the city include South Beach, Rest Beach, Higgs Beach, Simonton Beach and the Smathers Beach are great options. 

You will like Rest Beach for a nice time under the sun for a picnic. You will find picnic tables here. 

Food and culture tour 

A food tour is a great way to experience the city’s culture and cuisine. This 3-hour guided small-group tour takes you to 6 tasting locations. Tastings range from local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. You will be able to truly see, eat how locals do.  

You will also get to learn about the history of Key West along the way, and also receive a collection of exclusive recipes from your stops and keep them as souvenirs. Book your 3 hour food tour here

Sunset Cruise & Key West Sunset Celebration

Sunsets are mesmerizing in Key West. The ‘See you at Sunset’ phrase summarizes the spirit of the city. Mallory Square is a popular spot to ring in the evening vibes with celebrations, and hop on a sunset cruise with dinner abroad. 

The Key West Sunset Celebration takes place at the square. This ‘event’ started in the 1960’s and even today just before sunset, spectators get together to soak in the golden hues over the horizon of the Gulf of Mexico. 

Along with natural beauty, you are surrounded by performers from magicians, jugglers, to local musicians, and food vendors for a spectacular evening!

The  sunset cruise is also a lovely add-on to your evening. The cruise begins on “The Party Cat”, and it lasts for 2 hours, where you get to enjoy a buffet dinner and an open bar. 

After dinner, you are welcomed to the upper deck for live music and dancing. Don’t forget to bring a light scarf, and your camera to capture the gorgeous night sky and the waters.

You can book a sunset cruise with dinner here

Day trips from Key West: 3 days in Florida Keys Itinerary or more

To extend your trip from Key West, you can add visits to national and state parks. 

Key West to Miami Road Trip

If Key West is your entry to Florida, then visiting Miami from there, is recommended. 

The road trip from either way is worth it, as it is filled with blue beaches, and leafy trees. It takes 3.50 hours one way, and you get to explore one of the finest cities in the US. 

There are awesome places to stop along the way. Here are some road trip stops to consider, 

• Big Pine Key: Perfect for outdoorsy activities like fishing, and admiring the beautiful coastal scenery.
• Marathon : Key to Marathon is about an hour’s drive away. It is set on 13 islands in the Florida Keys and is known for tropical activities. On the southern edge is the Seven Mile Bridge – Overseas Highway. Although it takes 4 hours to complete the drive, you can surely admire the endless blue water views here. The bridge has two traveling lanes, and you can enjoy trails next to the highway or stop for a picnic.
• Islamorada: Key West to Islamorada is about less than 2 hours. It is a pretty village in Monroe County. It is known for its coral reefs, dolphins, and the Diving Museum. This spot is perfect for a rest spot. The Florida Keys Brewing Co. located at Islamorada (Old Hwy) is a travelers favorite for light beer, fish tacos, and live music. 
• Key Largo: You can explore Key Largo as a day trip from Key West, or stop as you drive from Key West to Miami. It takes about 2 to 2.50 hours to get there. Key Largo is home to the world’s second largest artificial reef, beaches, and beautiful resorts. Do visit Key Largo Conch House for delicious seafood and key lime pie.

From Miami, do include a trip to Biscayne National Park . (Key West to Biscayne National Park is 3 hour by road, so a day trip will be too much. But you can visit Biscayne National Park and then proceed to Miami instead). 

Day trips from Key West

Bahia Honda State Park: From Key West you can also explore the Bahia Honda State Park. It takes about 50 minutes to get there by car. You can reach there via public transportation (located at mile marker 37 in the Florida Keys). 

This State Park features an award winning beach and historic bridge. 

Dry Tortugas National Park: Dry Tortugas National Park is located west of Key West, and it takes about 2 hours and 15 minutes to get there by ferry. Dry Tortugas comprises 7 islands, and coral reefs. 

At the park, you can explore 19th-century Fort Jefferson and relax at a beach. When traveling from Key West, set aside 4-5 hours at the National Park. 

Everglades National Park: There are other national parks in Florida that you can visit from Key West, the most popular one worth exploring is the Everglades National Park (2.50+ hours by road one way). 

Well known for its subtropical wetlands, from coastal mangroves, and marshes, the Everglades is home to hundreds of species of animals such as leatherback turtle, Florida panther and West Indian manatee.

There are tons of easy to challenging hikes that you can embark on at the Everglades. On a day trip you can also explore by enjoying short walks and strolls on well marked boardwalks, go on an airboat tour, or join a Shark Valley Tram tour. National Park fees apply. 

What to pack for a trip to the Florida Keys?

Being a tropical destination, we wanted to share a packing list for your trip,

• Sunscreen and sunglasses : Regardless of the month of visit, you must carry sunscreen and sunglasses to provide against harmful UV rays. Reapply sunscreen when necessary.
• Walking Shoes: Since the city is walkable, bring in your best and comfortable walking shoes
• Beach essentials: Don’t forget flip flops, swimwear, shorts, a hat, and a beach bag 
• Water shoes
• Breathable clothes : Carry and wear airy and breathable fabrics. Pack flowy dresses in different colors. 

Sightseeing Map with stops for 2 day Florida Keys Itinerary

Additional Key West Travel Tips: Key West Itinerary 2 days

2 days are perfect to explore Key West. You can set aside a day for exploring the iconic city attractions such as Key West Historic District – Truman House, Hemingway House, Key West Cemetery and Duval Street.  Keep the second day for watersports and sunset sail.

2 to 3 days are enough for Key West. With an extra day in the city you can either visit one of the national or state parks on a day tour. Or pick more water sports.  Other than snorkeling and dolphin watching, you can also go on eco tours, jet skiing, and sailing/parasailing, without being rushed. 

A minimum of 3 days is necessary to drive from Key West to Florida keys, and check off the prime attractions, and stop/relax too.

The best time to visit Key West Florida is from March to May when the weather is pleasant for sightseeing – it is not too hot. Plus the peak crowds (from December to March) would have disappeared during that time allowing for better hotel and flight deals.  Winters are very busy and crowded here, and it is the busiest time of year to visit Key West.  Off season months are from June to November, but summers are hot. September and November are the cheapest for hotels and flights.

It is possible to travel to Key West on a budget. Booking during the off season is key to save on flights, hotels and tours. The city is walkable, so you don’t have to spend on renting a car.  City sightseeing doesn’t have to be expensive either, you can walk to various attractions, admire the coastlines/beaches, and opt for self guided tours. In terms of food, there are tons of casual and affordable food vendors that you can rely on for your meals in Key West.

We hope you found this suggested 2 day Key West itinerary useful in planning your next getaway to Florida!

Pin: How to spend 2 days in Florida Keys itinerary

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The Ultimate 3 Day Key West Itinerary (With a Map of Key West)

Are you planning your ultimate Key West vacation but not sure where to start? Keep reading!

In this 3 Day Key West itinerary , I cover all the details you need to know to plan your dream vacation to Key West . I’ll go over the best areas to stay and different hotel options, the top restaurants to check out, and all the fun activities you need to do!

In my opinion, 3 days is the perfect amount of time to spend in Key West for first-timers. 3 days gives you the opportunity to soak in the atmosphere, explore the main sites, and go on 1-2 excursions if you wish!

So whether you’re a history buff, a nature enthusiast, or simply seeking the perfect beachside retreat, this Key West itinerary is designed to make the most of your time in the Conch Republic!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

The Ultimate Key West Itinerary: 3 Days in the Conch Republic

Where to stay in key west.

Before we dive into this Key West itinerary, let’s talk about where to stay in the famous Key West!

Key West is only 4 miles long, so you might be thinking… how many places can there possibly be to stay? The answer is… a lot!

Key West has a few diverse neighborhoods, but the first decision you’ll need to make is whether you prefer the historic charm of Old Town or the modern amenities of New Town. These two areas split Key West down the middle: the eastern half and the western half.

Most people want to stay in Old Town to be near the action, but there are pros and cons to both areas, which I’ll dive into in the next sections!

Staying in Old Town Key West

For those seeking a slice of Key West’s rich history and vibrant atmosphere, Old Town is the ideal choice. This area is known for its charming streets lined with Victorian-style houses, art galleries, and boutique shops.

When staying in Old Town, you’ll be steps away from the iconic sites. You can explore the Hemingway Home and Museum, soak in the vibrant energy of Mallory Square, and party the night away on Duval Street, then walk back to your accommodation!

Here is a list of the top Old Town Key West hotels , but you can also check out your options on the map above! Old Town has tons of vacation rental and B&B options as well as typical hotels!

• Almond Tree Inn (Moderate)
• Ocean Key Resort (Moderate/Luxury)
• Pier House Resort & Spa (Moderate/Luxury)
• Casa Marina Key West (Luxury)

If you’re staying in Old Town, I recommend skipping the rental car . You’ll be able to access everything you need via walking or biking. Parking in Old Town can be difficult and expensive, so it’s better not to have a car!

However, if you plan to visit other Keys during your stay, you’ll definitely need a car ! I recommend doing an epic road trip from Key Largo to Key Wes t so you can experience all the Keys have to offer!

🚗 If you are planning a road trip, I love using RentalCars.com to compare pricing across multiple companies! Plus, they have a great 48-hour cancellation policy!

Staying in New Town Key West

If you’re driving into the Keys, New Town is the first area you’ll come across. It’s where the airport is located, along with most of the “chain” hotels. This area is characterized by wider streets, modern conveniences, and a quieter ambiance compared to the lively energy of Old Town.

New Town provides a more relaxed environment, making it an excellent choice for those looking to unwind after a day of exploration. It’s also convenient for those who prefer to have modern amenities at their fingertips.

Hotels in New Town also tend to be a bit cheaper than those in Old Town!

Even though it’s a bit further away from the main Key West attractions, you still may not need a car if you’re staying in New Town.

This is because most of the hotels in New Town have free shuttles to Old Town that run multiple times a day. These shuttles make it easy to visit Old Town without having to worry about parking, or drinking and driving!

Here is a list of the top hotels to check out in New Town Key West!

• Havana Cabana at Key West (Budget/Moderate)
• Parrot Key Hotel & Villas (Moderate)
• Margaritaville Beach House (Moderate)
• The Perry Hotel and Marina (Moderate)
• Hilton Garden Inn (Moderate)

How to Get to Key West

If you’re planning a Key West vacation, you’re going to need to know how to get there! There are a couple of options when it comes to traveling to Key West.

The Key West International Airport (EWY) is extremely convenient to fly into. It’s located right in the heart of New Town and just minutes away from Old Town. If you have the option, I highly recommend flying into Key West.

However, you may find that flights into EWY can be a little pricey. While there are direct flights from around the country, it is still a small airport, which tends to mean higher prices. Airlines like Silver and Allegiant often have cheap, direct flights though, so check to see if they fly out of your home airport!

The other option is to of course: drive! If flight prices into Key West Airport are too high, you can look into Miami Airport (MIA) or Fort Lauderdale Airport (FLL) and then make the drive down to Key West.

I touch more on this in my Ultimate Florida Keys Travel Guide , but I highly recommend this route so you can experience ALL of the Keys, not just Key West. The best option is to fly into Miami, rent a car , and make the drive from Miami to Key West .

Once you arrive in Key West, you can drop off your rental car and fly out of the Key West airport, so you don’t have to drive the length of the Keys twice!

Make sure to book your rental car in advance ! I love using RentalCars.com to compare pricing across multiple companies.

🚗 Check rental car availability for your trip here! 🚗

Key West Map

Lastly, before we get into this Key West itinerary, here is a detailed map of Key West! It includes all of the restaurants, bars, and landmarks mentioned in this itinerary, plus more!

Make sure to save this map of Key West to your own Google Maps so you can access it during your trip!

Need help planning your trip to the Florida Keys?

Planning a trip to the Florida Keys doesn’t have to be stressful! As a Florida local who’s visited the Keys over 20 times, I’ve put all my knowledge and insider tips into this  Florida Keys Digital Travel Guidebook!! 

This guide offers everything you need in one place – from where to stay and what to do, to the best times to visit and essential driving tips. With detailed breakdowns of each Key, 2 sample itineraries, a packing checklist, plus an  exclusive Google Map with over 100 pinned locations , it’s designed to make your trip easy and unforgettable! 

Day 1: Brunch, Historic Sites & a Sunset Celebration

Blue heaven + exploring old town.

Today is your first full day in Key West! Welcome to paradise!

Start your morning by heading straight to Blue Heaven , one of the most popular restaurants. They open at 8am , and I recommend getting there as close to opening as possible. If you show up later in the morning, be prepared to wait!

I highly recommend getting the Lobster Eggs Benedict and a slice of their GIANT Key Lime Pie!

After breakfast, it’s time to walk around Old Town Key West and explore the historic sites. There are a ton of things to do in the area, so you can choose a few (or all!) of them to fill your morning. Here are a few options!

• Climb to the top of the Key West Lighthouse
• Snap a picture at the Southernmost Point
• Tour Ernest Hemingway’s Home & Museum
• Explore the Key West Butterfly and Nature Conservatory

Note: If you are planning a trip from Miami to Key West, you can grab the Go City Miami Pass which includes includes access to tons of different attractions!

Another fun option is to go on a cultural and food tour in Key West ! Key West is a blend of Florida, Cuban and Caribbean culture which means incredible food to try!!

There are also some great lunch spots around this area, including The Lobster Shack , the Seaside Cafe at the Mansion , and Louie’s Backyard !

Beach Relaxation & Sunset Views

In the afternoon, head over to Fort Zachary Taylor State Park , a 19th-century fort and park located on the southern edge of Key West. Starting at $4.50 per person, the park is a great place to spend an afternoon.

There is a beautiful beach within the park where you can swim, lounge, and even snorkel ! Plus, you can explore the fort’s grounds and learn about the incredible Civil War history.

To finish off your day, make your way to Mallory Square and witness the famous Sunset Celebration . This is the most famous place to watch the sunset in Key West, so if you want a front-row seat, arrive early!

Around sunset, Mallory Square comes alive with food vendors, street performers, music, and more. It’s the perfect way to finish off your first night in Key West.

Day 2: Ocean Adventures & Duval Street

A morning ocean adventure.

On Day 2 of this Key West itinerary, it’s time to get out on the water. You have a couple of options!

If you’re feeling adventurous, I highly recommend visiting Fort Jefferson at Dry Tortugas National Park. a former military installation approximately 60 miles west of Key West in the middle of the ocean.

To get here, you either need to take the 3-hour Yankee Freedom ferry or book a seaplane . (The latter is very pricey!!). Both options book up pretty far in advance, so I recommend looking at your options as soon as possible! You can read more about visiting here .

Fort Jefferson is one of the coolest places I’ve ever visited! The fort was never finished, but it was used during the Civil War and even held prisoners.

You can spend the day walking around the fort and enjoying the scenery. Plus there are incredible beaches and clear water surrounding the fort that you can snorkel and swim in. You can even camp here if you’re into that!!

If Fort Jefferson doesn’t sound like your cup of tea, there are plenty of other ocean adventures to be had locally in Key West. My top recommendation is going on a reef snorkeling adventure !! The underwater landscape is what makes the Florida Keys famous, so going on a snorkel tour is a must do in Key West.

🤿 Check pricing and availability for reef snorkeling in Key West here ! 🤿

Make sure to grab breakfast at the Cuban Coffee Queen before your adventure!

A Night on Duval Street

In the evening, head back down to Old Town and grab dinner at one of the fabulous restaurants nearby. If you want to be on the water, I highly recommend Hot Tin Roof at the Ocean Key Resort. This is a great spot if you can’t get enough of those Key West sunset views! You can also grab pre-dinner drinks at Sunset Pier!

There are also some incredible restaurant options along Duval Street, including Blackfin Bistro , Kaya Island Eats , and Nine One Five .

After dinner, it’s time to check out the famous nightlife in the area and maybe do the “Duval Crawl”. This is the nickname for bar-hopping along Duval Street, as you will be crawling by the end!

➡️ Read Next: Should You Visit Key West in December? Yes! Here’s Why

Some of the most famous bars on Duval include Hog’s Breath Saloon, Sloppy Joe’s, the Bull and Whistle Bar, and the Smokin’ Tuna Saloon.

If dive bars aren’t your thing, don’t worry! There are other nighttime options on Duval Street. You can grab an incredible, adult-friendly dessert at the legendary Better Than Sex restaurant. Another option is to see a drag show at Aqua Nightclub or La Te Da ! Or you can just wander down the street and appreciate the chaos.

Day 3: Bikes, Beach, & a Sunset Cruise

Biking to the beach.

On the last day of this Key West itinerary, start your morning by renting bikes and exploring the south side of Key West. There are plenty of places to rent bikes from, but I highly recommend Eaton Bikes ! They will even drop off the bikes at your hotel for you.

Key West is extremely bike-friendly, so don’t worry about following a particular route, just make your way towards Smathers Beach. There’s a beautiful bike and walking path along A1A in front of the beach you can check out!

Once you’re ready to rest, head onto the gorgeous Smathers Beach, one of the only sprawling white-sand beaches in the entire Florida Keys! This man-made beach actually had white sand imported from the Bahamas, and it does not disappoint! It’s one of my favorite free things to do in Key West !

Shopping and Sunset Cruise

In the afternoon, head back down to Old Town and explore any other sites you missed on your first day. Around Mallory Square, there’s the Key West Aquarium, the Truman Little White House, and the Maritime Museum!

It’s also fun to explore Duval Street during the day! There are many great boutiques and souvenir shops to check out. Make sure to stop in Kermit’s Key Lime Pie Shoppe for another slice of Key lime pie!

In the evening, it’s time to close out your last night in Key West by embarking on a sunset cruise ! As you already know, the sunsets in Key West are jaw-dropping, and the best way to see them is from the water on a sunset sail.

Sebago Watersports Sunset Sail

• Duration : 2 hours
• Rating : 4.5/5 stars⭐
• Includes : Open Bar, Live Music, Appetizers

There are tons of different Key West sunset cruises to choose from, including dinner cruises, open bar cruises, and cruises with a dance floor! They typically last between 2 and 3 hours and will take you around Key West and Sunset Key as the sun sinks into the ocean.

You can check out my complete guide to Key West Sunset Cruises here to compare prices and help pick the perfect one for you!

Final Thoughts

That wraps up my perfect 3 Day Key West itinerary. As you can see, Key West is more than just an island destination; it’s a kaleidoscope of history, culture, and natural beauty that is sure to leave you wanting more!

And 3 days is the perfect amount of time to spend in Key West to be able to see and do it all. If you follow this 3 day itinerary, I guarantee you’ll have an incredible time!

Don’t forget to check out my other Florida Keys blog posts to help plan your epic adventure! 25 Epic Things to Do in Key West Best Time to Visit the Florida Keys Key Largo vs Key West Should You Visit Key West in January? Yes! Here’s Why

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The Perfect 3 Days In Key West Itinerary (2024 Guide)

• Last Updated: June 24, 2024

Check out our ultimate 3 days in Key West itinerary, including all the highlights of this stunning destination in the Florida Keys!

Key West , the southernmost city in the continental United States, is known for its irresistible charm, vibrant culture, and tropical allure.

With colorful conch-style houses, historic landmarks, and vibrant sunsets, this island paradise captivates visitors with its unique blend of Caribbean influence and American flair.

From the lively energy of Duval Street’s bars and restaurants to the beauty of its secluded beaches, Key West offers a diverse array of experiences for every traveler.

To help you plan your exploration of the Florida Keys, we’ve created the ultimate Key West itinerary for those who have 3 days in Key West. This convenient itinerary outlines the best parts of the area and even includes fun day trips and excursions.

Whether indulging in fresh seafood at waterfront eateries, exploring the eclectic art scene, or snorkeling amidst vibrant coral reefs, there are so many amazing things to do with 3 days in Key West!

Find more things to do nearby with our list of the 20 BEST Things to Do in Key West, Florida .

Table of Contents

Southernmost Point Buoy

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Here is our ultimate 3 days in Key West itinerary! Whether you’re a Florida local looking to explore more of the Sunshine State , or you’re an international guest on an exciting Florida Keys road trip , 3 days in Key West is sure to be an adventure for you.

On the first day of your Key West itinerary, explore the heart of the island. The Old Town is the most captivating part of Key West, so you’ll spend the entire day and night down here taking in all the sights.

You can explore most of these Old Town attractions on foot, or you can cover more ground by booking a bicycle tour . Either way, have a blast exploring the heart of Key West on the first day of your 3 days in Key West itinerary!

Morning: Historic District Attractions

Here are some of the top sights to include in your exploration of the Old Town, from the Southernmost Point to the Key West Lighthouse and more. We’ve listed them in order of location so you can conveniently walk from one attraction to the next.

The Southernmost Point Buoy is an iconic symbol of Key West’s unique geographical location and is a must-visit landmark for travelers exploring the island.

Situated at the southernmost point of the continental United States, this colorful buoy marks the spot where the Atlantic Ocean meets the Gulf of Mexico.

Visitors flock to this beloved landmark to snap photos with the buoy, which is adorned with vibrant colors and markings indicating its distance from various locations, including Havana, Cuba, and the North Pole.

Another fun place to check out near the Southernmost Point is the Key West Butterfly and Nature Conservatory .

This serene sanctuary is home to thousands of colorful butterflies from around the globe, flitting gracefully amidst tropical flowers and cascading waterfalls in a lush, climate-controlled habitat.

As visitors wander through the winding pathways, they are immersed in the sights, sounds, and scents of this magical ecosystem, encountering exotic species such as the vibrant Blue Morpho and the delicate Monarch butterfly.

The Key West Butterfly and Nature Conservatory provides a captivating opportunity for nature lovers of all ages to marvel at natural beauty in Key West.

Plan to visit Miami first? Here is our ultimate Miami To Key West Road Trip Itinerary !

The Key West Lighthouse , an iconic maritime landmark, rises majestically above the historic streets of Key West, providing travelers with a glimpse into the island’s rich maritime history. Originally built in 1825 to guide ships through the treacherous waters surrounding the island, the lighthouse stands as a testament to Key West’s heritage.

Today, visitors can climb the 88 steps to the top of the tower, where they are rewarded with breathtaking vistas of the turquoise waters of the Atlantic Ocean and the vibrant rooftops of Old Town Key West.

With its historic charm and stunning views, the Key West Lighthouse provides a captivating opportunity for visitors to immerse themselves in the island’s maritime past and gain a newfound appreciation for its timeless beauty.

The Ernest Hemingway Home and Museum celebrates the prolific writer’s time spent in Key West and showcases remnants of his life and legacy.

Situated amidst lush tropical gardens in the heart of Old Town Key West, you can explore the Spanish colonial-style home where Hemingway lived and worked from 1931 to 1939. Guided tours lead visitors through the meticulously preserved interiors, showcasing the author’s personal belongings, furniture, and mementos.

With its rich history, timeless charm, and resident population of six-toed cats, the Ernest Hemingway House and Museum offers a unique and immersive experience that celebrates the legacy of one of the 20th century’s most iconic literary figures.

Next on your 3 days in Key West itinerary, walk about 15 minutes down to Fort Zachary Taylor Historic State Park .

Fort Zachary Taylor Historic State Park is situated along the southern coast of Key West. It’s home to a 19th-century fortress that was built to defend Key West’s strategic harbor. You can walk through the interpretive exhibits and enjoy a range of outdoor activities, including swimming, snorkeling, and picnicking on the park’s pristine sandy beaches.

With its tropical landscapes, panoramic ocean views, and historic attractions, Fort Zachary Taylor Historic State Park is an amazing place to visit in beautiful Key West.

Exploring more of the Sunshine State? Read our list of the 25 Best Things To Do In Florida !

As the sun begins to set, take to the streets of Key West and fully indulge in the evening energy! Duval Street, the vibrant heart of Key West, pulsates with excitement, offering visitors an eclectic mix of entertainment, dining, shopping, and nightlife.

Stretching for just over a mile from the Gulf of Mexico to the Atlantic Ocean, this iconic thoroughfare is lined with historic buildings, colorful storefronts, and charming cafes, creating a lively and dynamic atmosphere that captivates visitors day and night.

There are street performers, live music, nightclubs, bars, and even a nightly sunset celebration at Mallory Square near the end of Duval Street. You can dance the night away, go bar hopping, or just grab a nice dinner and stroll around.

From savoring fresh seafood at waterfront restaurants to sampling tropical cocktails at lively bars or maybe grabbing a slice of famous key lime pie, Duval Street is the perfect place to end a day of sightseeing during 3 days in Key West.

It’s day 2 of your Key West itinerary! Hopefully you didn’t get too crazy on the popular Duval Street last night because today is going to be an amazing day of adventures. In the morning explore Dry Tortugas National Park, then do more sightseeing around the Key West waterfront and finish off with a lovely sunset sail.

Today you’re taking a day trip to Dry Tortugas National Park, located approximately 70 miles west of Key West. It’s pretty far so you might want to get up early and turn it into a day trip.

But you really don’t want to visit this place while visiting the Florida Keys! Dry Tortugas National Park is a remote and pristine paradise consisting of seven small islands and their surrounding waters.

Accessible only by boat or seaplane, this protected marine sanctuary is renowned for its crystal-clear turquoise waters, vibrant coral reefs, and abundant marine life, making it a haven for snorkelers, divers, and nature enthusiasts.

At the heart of the park lies Fort Jefferson, a 19th-century coastal fortress and one of the largest masonry structures in the Western Hemisphere. Steeped in history and surrounded by breathtaking natural beauty, Fort Jefferson offers visitors the opportunity to explore its historic ramparts, artillery batteries, and underground passages while learning about its fascinating role in American history.

In addition to its rich history and unparalleled snorkeling and diving opportunities, Dry Tortugas National Park has pristine beaches and secluded coves where you can soak in the natural beauty of the Florida Keys.

With its remote location, stunning landscapes, and abundant recreational opportunities, Dry Tortugas National Park offers a unique and unforgettable wilderness experience for those seeking adventure, relaxation, and connection with nature in one of America’s most remote and pristine national parks.

Find out more about how to visit Dry Tortugas National Park on the National Parks website !

Afternoon: Explore the waterfront

When you arrive back after your time in Dry Tortugas National Park, you might be pretty tired but you still have a sunset cruise tonight. You can spend whatever free time you have strolling around the Key West waterfront and checking out some attractions or just grabbing food or drinks at a restaurant. If you are up for more sightseeing, here are some of the top sights to check out.

The Key West Historic Seaport is a vibrant and historic hub of the area. Steeped in maritime history dating back to the 19th century, the seaport is home to a picturesque collection of wooden docks, historic buildings, and colorful fishing boats that evoke the island’s rich heritage.

This is a great place to just go for a walk, grab some food, and relax by the water. If you have more than 3 days in Key West, you can also come down here to book sailing excursions, fishing charters, and kayak rentals.

The Key West Historic Seaport offers a range of recreational activities and experiences that celebrate the island’s deep connection to the sea, making it a must-visit destination for travelers seeking to immerse themselves in the vibrant culture and maritime traditions of Key West.

Read next: 2-Week Florida Road Trip Itinerary

You may have already visited Mallory Square on your night of bar hopping! If not, definitely make time to check out this exciting plaza located at the western end of Key West’s historic Old Town during your itinerary.

Renowned for its nightly Sunset Celebration, Mallory Square comes alive each evening with live music, street performers, and vendors selling local crafts and cuisine, creating a festive atmosphere that draws locals and visitors alike.

Not far from Mallory Square is the Key West Aquarium , one of the oldest aquariums in Florida! The aquarium provides a unique opportunity to encounter a wide array of marine life native to the region, including colorful tropical fish, graceful stingrays, and majestic sharks.

Through interactive exhibits and informative presentations, visitors can learn about the delicate balance of the coral reef ecosystem, the importance of marine conservation, and the fascinating behaviors of the creatures that inhabit these underwater worlds.

With its educational programs, touch tanks, and immersive experiences, the Key West Aquarium invites visitors of all ages to discover the wonders of the ocean right in the heart of the Florida Keys.

Explore more of the Florida Keys with a visit to Key Largo !

The Truman Little White House is a historic landmark that offers a fascinating look into the lives of past presidents and the rich history of the Florida Keys.

Originally constructed as naval officer housing in 1890, the building served as President Harry S. Truman’s winter White House during his presidency.

Today, visitors can explore the meticulously preserved rooms and grounds, which have been restored to reflect their appearance during Truman’s tenure.

Through guided tours and informative exhibits , guests can learn about Truman’s presidency, his personal life, and the significant events that occurred during his time in office.

Finish off this amazing day in the Florida Keys with a sunset sail with food and drinks . You can watch nature put on a show, cruise around the calm, tropical waters of the Florida Keys, and indulge in some food, drinks, and socialization.

A sunset sail is the perfect way to end any day in Florida!

On the final day of your 3 days in Key West, join an adventurous tour that includes some water sports so you can embrace the sunny weather and marine life of the Florida Keys. Choose from a dolphin watching and snorkelling tour, a kayaking tour, or a jetski tour, then finish off the afternoon at Smathers Beach and get some key lime pie to wrap up the weekend.

While exploring the Florida Keys, make sure you take ample time to frolic in the warm, tropical waters. Spot marine life such as dolphins or sea turtles, soak in the Florida sunshine, and just have lots of fun!

A popular option is a Dolphin watching and snorkelling eco tour of Key West. You’ll cruise around the Florida Keys and your guide will take you to spots where dolphins are often playing in the waves.

Snorkel and explore the underwater world as well so you can fully appreciate the beauty of Key West!

Another option is a jet ski tour , perfect for those who love adrenaline and fast-paced sports. Or if you prefer a more mellow tour for your weekend in Key West, join a kayak tour and paddle around the stunning Key West coastline.

After your exciting morning of water sports and marine life, kick back on Smathers Beach. This beautiful location stretches along the southern shore of Key West and is a picturesque haven of sun, sand, and surf.

As the largest public beach on Key West, Smathers Beach has soft white sands and crystal-clear waters that are perfect for sunbathing, swimming, and watersports.

With its breathtaking views of the Atlantic Ocean and vibrant atmosphere, Smathers Beach captures the essence of island paradise.

If you’re not in the mood to be a beach bum, you could also check out the nearby Key West Tropical Forest and Botanical Gardens . Spread across 15 acres, the gardens showcase a rich diversity of plant life, including rare and endangered species native to the Florida Keys.

Visitors can wander along shaded pathways, discovering a colorful array of flowering plants, towering palms, and exotic trees, while listening to the soothing sounds of nature.

To finish off your action-packed 3 days in Key West, get some of the best key lime pie in the Florida Keys. Kermit’s Key Lime Pie Shoppe is a beloved culinary institution in Key West celebrated for its iconic Key lime pies and irresistible sweet treats.

Using traditional recipes passed down through generations, Kermit’s pies are crafted with locally sourced Key lime juice, resulting in a perfect balance of tartness and sweetness.

Beyond its signature pies, the shop offers an array of Key lime-infused treats, from cookies and candies to sauces and marinades.

With its charming ambiance and delectable offerings, Kermit’s Key Lime Pie Shoppe embodies the essence of Key West’s culinary heritage, and is the best place to taste a classic key lime pie.

See more of Florida’s East Coast with a visit to Fort Lauderdale !

Key West Travel Guide

Now that we’ve covered how to spend a weekend in Key West, here are some helpful travel tips that will help you plan your trip. From the best months to visit, to tips for getting around and accommodation recommendations, you’re well-equipped for the perfect weekend in Key West!

The best time to visit Key West largely depends on your own preferences. Because it’s located in the Florida Keys, the weather is tropical and you can visit year-round! But certain seasons bring a different vibe and temperature to Key West, and many travelers find that the period from late fall to early spring has the best weather.

From November to April, Key West experiences mild temperatures ranging from the 70s to 80s Fahrenheit, making it ideal for outdoor activities such as snorkeling, sailing, and exploring the island’s historic sites and natural wonders.

Additionally, this time of year sees fewer crowds and lower humidity levels in the Florida Keys, allowing visitors to enjoy the island’s attractions and beaches without feeling overwhelmed by tourists.

While the summer months from June to August can bring warmer temperatures and higher humidity, they also offer opportunities for exciting events and festivals, including the Key West Hemingway Days and the Key Lime Festival.

Despite the occasional afternoon shower, summer in Key West is still a popular time to visit for those seeking lively nightlife, vibrant street performances, and water sports such as jet skiing and parasailing.

Additionally, hotel rates may be lower during the summer months, making it a great option for budget-conscious travelers.

Ultimately, the best time to explore Key West depends on your own travel style, but each season offers its own unique charm and opportunities for exploration.

Definitely, the best way to get around during your weekend in Key West is to have your own car. If you don’t already have a car, consider renting one in Key West! Alternatively, you can rent a car somewhere in mainland Florida, like Miami or Orlando, and do an epic Key West road trip.

There are other options for visiting Key West without a car as well. Getting around Key West is relatively easy and convenient, with various transportation options available to suit every traveler’s needs.

Many visitors opt to explore the island on foot or by renting bicycles, allowing them to navigate the charming streets of Old Town and discover hidden gems at their own pace.

Additionally, the Key West Transit system operates buses that connect popular attractions throughout the island, providing an affordable and convenient way to get around. For those looking to explore further afield or visit neighboring islands, taxis and rideshare services are readily available.

Renting a scooter or electric car offers a fun and efficient way to explore the narrow streets and iconic landmarks of Key West. Or you can book a Hop on hop off Old Town trolley and explore the highlights of the Old Town on a fun, historic trolley car.

With its compact size and diverse transportation options, getting around Key West is a breeze, allowing visitors to make the most of their time on this enchanting island paradise.

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Where to stay in Key West

Here are some of the best places to stay in Key West during your weekend trip. We’re going to list options for all types of budget ranges, though to be honest, Key West is not cheap! Even the cheapest motels are a bit on the expensive side, going for at least $250 USD per night.

However, a weekend in Key West is meant to be a bit indulgent, so don’t be afraid to treat yourself! And we’ll list a great budget motel that is as cheap as it gets in Key West.

Read next: 21 Best Things To Do In Fort Myers, Florida

The Blue Marlin Motel is one of the most affordable places to stay during your weekend in Key West, and it still gets great reviews! Complete with free continental breakfast, an outdoor pool, free wifi, and coffee facilities and work desks in the rooms, you have everything you need here for a comfortable stay.

Blue Marlin Motel is also perfect for a weekend in Key West because it’s just a short walk from local attractions like the southernmost point of the continental US and the Key West Butterfly & Nature Conservatory. If you have a car, it’s also just a short drive from the bustling Duval Street and the Ernest Hemingway Home and Museum.

Take your accommodation up a notch during your 3 days in Key West with the Truman Hotel , located right near the Key West Old Town and within walking distance from the best local attractions.

Named after the iconic former president who once called Key West home, this boutique hotel captures the essence of island living with its chic and modern design blended seamlessly with historic charm.

The meticulously appointed rooms and suites evoke a sense of tropical elegance, featuring contemporary furnishings, plush bedding, and upscale amenities. Guests can unwind in the hotel’s lush courtyard oasis, complete with a sparkling pool and tropical landscaping, or venture out to explore Key West’s famed attractions, including historic landmarks, world-class dining, and picturesque beaches.

Perched along the sparkling shores of Stock Island in Key West, Ocean’s Edge Hotel embodies the epitome of luxury and relaxation in the Florida Keys. With gorgeous views of the turquoise waters of the Atlantic Ocean, this waterfront retreat offers guests a serene escape during their weekend in Key West itinerary.

The Key West hotel’s contemporary design and upscale amenities create an atmosphere of modern elegance, with spacious suites and villas featuring private balconies or patios overlooking the ocean or lush tropical gardens.

Guests can indulge in gourmet dining at the hotel’s waterfront restaurant, unwind by the infinity-edge swimming pool, or explore the nearby attractions and vibrant culture of Key West. With its tranquil setting and unparalleled waterfront location, Ocean’s Edge Hotel is one of the best upscale accommodations in the Florida Keys!

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Alesha and Jarryd

Hi, We’re Alesha and Jarryd!

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

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Weekend in Key West: The Perfect 2 or 3 Day Itinerary

Key West is one of the most vibrant and quirky cities in the US, and has the perk of being located in a tropical climate. Therefore, many people choose this island city as their vacation destination each year. There are plenty of fun experiences to be had, and this itinerary for 3 days in Key West will ensure you see the best of everything.

Although Key West is surrounded by water, it is connected to the mainland United States via a series of bridges through the Florida Keys called the Overseas Highway, or Highway 1. The endpoint of Highway 1 can be found at the corner of Fleming Street and Whitehead Street in downtown Key West.

Its unique location is just one thing that sets Key West apart from every other US city. Whether it’s bar hopping, foodie spots, sightseeing, or enjoying the great outdoors, there is something for everyone to enjoy in the “Conch Republic”. Without further ado, here is the perfect itinerary for an unforgettable 3 days in Key West .

3 Days in Key West – Itinerary for First Time Visitors

Day 1: Explore Classic Key West

Day one of this Key West itinerary focuses on getting an overview of the city and visiting some of its most famous landmarks.

Arrive into Key West & Rent Bikes

You will likely arrive in Key West by flying into Key West International Airport (EYW) or driving in via Highway 1. If you flew, the airport is only 11 minutes from Duval Street, which is Key West’s famous main drag. You can simply grab an Uber from the airport to your lodging if you don’t rent a car.

Your next step is to rent bikes for the duration of your stay from Key West Bicycles . With the island being only four miles long and two miles wide, a car is not necessary and a bike will be more economical for reaching destinations just outside of walking distance.

If you enjoy guided tours, this guided bike tour is a great introduction to the top attractions.

Southernmost Point Concrete Buoy

No Key West itinerary is complete without a stop at the Southernmost Point Concrete Buoy. Located at the corner of South Street and Whitehead Street, this large buoy marks the Southernmost Point of the Continental United States. While the accuracy of this claim is questionable, other points in the Keys that are further south are not nearly as accessible to the public.

Upon arrival to the big concrete buoy, you will most likely need to wait in line for your photos, unless you arrive first thing in the morning. However, the line moves fast and people are generally very cooperative in helping one another take pictures.

Hemingway Home & Museum

One of the most essential places to visit in Key West is the Ernest Hemingway Home & Museum . This is where Ernest Hemingway lived with his second wife, Pauline, from 1931 until their divorce in 1940. Hemingway wrote some of his most significant works in his studio above the carriage house.

While at the Hemingway House, you’ll likely see many cats roaming about.  If you look at their paws, you may notice that many of them have six toes!  Some of these cats are descendants of a 6-toed cat Hemingway received from a sea captain, who was departing Key West.

This house museum is open every day to walk-ins from 9am to 5pm, and the $16 ticket must be paid in cash. The price includes a 20 to 30-minute guided tour of the house.

Brunch at Blue Heaven

From the Hemingway House, walk four minutes to Blue Heaven , which is one of Key West’s most famous restaurants. Be sure to arrive by 2:00pm to make it in time for the breakfast & lunch menu. There is often a wait since they do not take brunch reservations, but it’s totally worth it.

Blue Heaven offers a variety of pancakes and benedicts, with some delicious options being the pineapple pancakes and Key West shrimp benedict. There is both indoor and outdoor seating, but outdoor allows you to eat in a garden-like setting with eclectic art, cats and chickens roaming about, and large tree canopies overhead. Save room for a slice of their signature key lime pie, which is piled high with merengue.

Key West Lighthouse

Burn off some of your brunch with a short climb up the Key West Lighthouse , which is just a four-minute walk from Blue Heaven. The current structure was built in 1848 after the original was destroyed in a catastrophic hurricane. It reopened with a woman, Barbara Mabrity, as its Keeper – a highly unusual circumstance at that time.

After climbing 88 steps to the top, you will be rewarded with panoramic views over Key West and the surrounding waters of the Atlantic and Gulf of Mexico. Tickets cost $17 at the door or $15.40 online, and give you access to the lighthouse and Keeper’s Quarters Museum. Visitors are welcome daily from 10am to 4pm.

Check out Duval Street

One of the most fun things to do in Key West is spending an evening on Duval Street, which is notorious for its party scene. There are plenty of spots to grab dinner, as well as make a night of it with drinks afterwards. Here are two casual and delicious dinner options:

• D.J.’s Clam Shack : DJ’s Clam Shack was once featured on Diners, Drive-Ins and Dives and is famous for their “overstuffed” lobster rolls and conch fritters. Order at the small counter just off Duval Street, and enjoy their mouthwateringly good food on the small back patio.

• Poké in the Rear : Visit this open-air restaurant behind the Aqua Bar and Night Club for super fresh and delicious poké bowls.

Afterwards, you may want to continue your evening with drinks on Duval Street. The street is lined with bars, but start at Sloppy Joe’s , which is an old standby once frequented by Ernest Hemingway. The drinks are standard, but there is usually live music and always plenty of atmosphere.

Day 2: Cuban Coffee & Sunset Sail

The second of your three days in Key West introduces you to the city’s most spectacular feature: its sunrise and sunset views. You will also get a taste of Key West’s strong Cuban culture.

Sunrise at Higgs Beach

Sunrises in Key West are absolutely stunning, and the best viewing spot is the Edward B. Knight Pier at Higgs Beach. You will need to get up really early for this, but it’s totally worth it. The sun rises anytime between 6:37am and 7:37am over the course of the year.

This is where you’ll be thankful to have a bike, since you won’t need to rise as early. Higgs Beach is only a five-minute bike ride from Duval, but it’s more like twenty if you walk.

Drink Cuban Coffee

Key West has a longstanding Cuban influence, being only 90 miles from Cuba.  Therefore, it’s imperative to try some Cuban coffee and cuisine while you’re in town.  Here are two great choices:

• Key West Cuban Coffee : This restaurant is located in a tiny space on Duval Street. Behind a small counter will be three ladies working nonstop at the grill and espresso machine. Cuban and Mexican fare is served here, including breakfast burritos, empanadas, and light Cuban coffee.
• Cuban Coffee Queen : Located in a shaded courtyard right off Duval Street, this outdoor restaurant is close to the action. You could keep things simple with a Cuban coffee or cortado paired with some pan Cubano. There are also more substantial items like Cuban sandwiches on the menu.

Butterfly Conservatory

Step away from Key West’s bustling scene for a moment without even leaving Duval Street. The Key West Butterfly & Nature Conservatory contains hundreds of living butterflies made up of over 50 different species.

In this glass enclosed space, you can wander past tropical plants with colorful blossoms, while the butterflies and over 20 species of exotic birds fly around you.  The conservatory is open every day from 9am to 5pm, and tickets cost $15.

Stop at Rum Bar

For some high-quality cocktails, stop in for a quick drink at the Rum Bar . This small bar is only a four-minute walk down Duval Street from the Butterfly Conservatory. The cocktails are a little pricey, but they are definitely among the best in all of Key West.

The Pusser’s Rum painkiller in particular is a must; especially when consumed while people watching on the bar’s front porch.

Sunset Sail

Rest up before heading back out for one of the best tours in Key West: a sunset sail. Like sunrises, sunsets in Key West are like no other, and they are especially spectacular to view from the water.

There are many different boat charter companies to choose from, and Danger Charters is among the best. Their sunset sail is two hours long and limited to twenty-five guests.

As the sun lowers onto the horizon and the sky turns brilliant shades of orange and pink, the crew serves wine and beer tastings paired with hors d’oeuvres. The atmosphere is relaxed and the views from the sailboat could not be any more magical.

Schooner Wharf Bar

If hors d’oeuvres during the sunset sail didn’t fill you up, a great next stop is Schooner Wharf Bar. This bar and grille is only a ten-minute walk or five-minute bike ride from Opal Key Resort & Marina, where the sailboat drops you off.

Schooner Wharf Bar sits waterside along the Key West Historic Seaport.  This restaurant isn’t fancy at all, with its simple wood structure and “patio seating” made up of tables and plastic chairs on top of gravel.  However, that’s part of its charm as you sip a cocktail and snack on some tuna nachos or fried shrimp.

Day 3: Last Day in Key West

Breakfast at glazed donuts.

Glazed Donuts is a Key West favorite due to its drool-worthy donuts baked Wednesday through Sunday of each week. The donuts are by no means skimpy and the dough has just the right amount of chew. They come in fun flavors like Cuban coffee, blueberry cheesecake, key lime pie, and seasonal varieties.

Arrive as early as possible, or be prepared to wait in a line that sometimes extends down the sidewalk. The shop is open until 1pm unless it sells out, and you won’t want to miss out on the best flavors.

Fort Zachary Taylor State Park

Spend some time outdoors at Fort Zachary Taylor State Park, which is located in downtown Key West, covers 54 acres, and has a beach and fort worth exploring. The fee to enter the park is $2.50 for walkers and bikers and $6 if you are parking a car.

While Key West is not a huge beach destination, this one is definitely worth a visit.  It offers beautiful scenery with its white sand and turquoise water that is popular for swimming.  There are chair and umbrella rentals available, or you can simply grab a picnic table and enjoy the view for a bit.

If you’d like to do some more exploring, check out Fort Taylor, which was built before the Civil War to defend the nation’s southeastern coast.  The fort was used in the Civil War, Spanish American War, WWI, WWII and the Cuban Missile Crisis, though it was never fired upon.

This state park also has the continental US’s southernmost hiking trails, including the Tropical Hammock Trail and Fort View nature trail.

Truman Little White House

The Truman Little White House is just a three-minute bike ride from Fort Zachary Taylor State Park, so it’s the perfect next stop on this Key West itinerary. While this house was used intermittently by six American presidents, its most significant usage was during Harry Truman’s presidency. He used the Little White House as his winter home, and spent about 175 days of his presidency here.

Tickets do not come cheap at $22.52 ($20.27 online), but a tour here allows you to see why Truman saw this as a retreat.  In this setting, he also would have contemplated issues surrounding post WWII foreign policy and the beginnings of the Civil Rights movement.

Kermit’s Key Lime Pie

Bike or walk .3 miles from the Truman Little White House to Kermit’s Key West Key Lime Shoppe on Front Street. This local establishment makes many lists for having one of the best key lime pies in Key West .

In addition to traditional pie, this little shop has an assortment of key lime treats that celebrate this flavor. A popular choice is chocolate covered key lime pie on a stick that you can nibble while walking around town. Just remember napkins for when the chocolate starts to melt in the tropical heat and humidity.

Mallory Square

In case you couldn’t already tell, the sunset is a big deal in Key West; so much so that there is a nightly Sunset Celebration in Mallory Square.  This is something you should experience at least once during your stay, and it’s just a two-minute walk from Kermit’s.

The celebration begins about two hours before sunset when local vendors and street performers gather for a large party in the square. There are magicians, psychics, and food stalls to name just a few, and they build anticipation for the orange glow of the sun to lower over Sunset Key.

Dinner at Latitudes

Top off your last night in Key West with an incredibly romantic and memorable experience: dinner at Latitudes . As this fine dining restaurant is located on Sunset Key, you will need to head back to the Opal Key Resort and Marina to catch the ferry. This is free to anyone with a reservation at Latitudes.

Be sure to make reservations at least one month in advance, if not more, as dinner here is very popular. However, it’s worth the hype to eat right on the water with your toes in the sand. Plus, they offer a sophisticated menu with plenty of fresh seafood dishes, as well as an excellent wine list. Dinner at Latitudes is guaranteed to end your Key West itinerary on a high note.

Key West Travel Tips

• Getting There: There are several ways to reach Key West. You fly into Key West International Airport . Miami is about 165 miles (or 266 kilometers) driving distance so you can also fly into Miami and rent a car or take a bus from Miami . If time is short, you can also visit Key West on a guided day trip from Miami .
• Getting Around: Renting a car is not recommended due to Key West’s congested traffic and limited parking spots. The island is only 2×4 miles, and the best sights are easily reachable via biking or walking. If you enjoy guided tours, you join a trolley hop-on hop-off tour or a conch train tour .
• Weather: Key West generally has pleasant weather year-round. High season is between December and February, and brings crowds and high prices; September through November is hurricane season, making this the least ideal time to travel. April is ideal, as the crowds have tapered off and the sweltering summer heat hasn’t set in yet.
• Where to Stay in Key West: If it’s your first time visiting Key West, your itinerary will likely center around Duval Street. Therefore, it’s best to stay in close vicinity of that main stretch. Old Town Garden Villas is just one block from Duval, and has an adorable courtyard with a small dipping pool.

You are now all set with the perfect 2 or 3 days in Key West itinerary. Be prepared for the best sunsets you’ve ever seen in this eternally festive, yet laid back atmosphere. Just remember to pace yourself and keep an open mind to all the quirks this city has to offer.

Theresa’s Bio: Theresa is the creator of Fueled By Wanderlust , a travel blog. Although she did not start traveling until her mid-twenties due to some pesky student loan debt, with careful budgeting, she was able to pay that off and start planning trips. Since then, she has traveled more and more each year to various places in the U.S., Europe, and the Caribbean. You can follow along with Theresa’s adventures on Instagram , Twitter , and Facebook .

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A Weekend in Key West – The Best Things to Do in 2 to 3 Days

A weekend visit to tropical Key West, Florida offers unforgettable experiences mixing history, culture, natural beauty with lots of fun!  Enjoy the city’s rich history where authors, artists and adventurers have all made their mark.

Whether you want to simply relax or get that adrenaline kick, Key West has it all!

Table of Contents

Key West Itineraries

We have the perfect itinerary, no matter long you’re in Key West.

How Many Days in Key West?

Spend at least one full day in Key West.  Old Town ’s historic area is relatively small.  Its highlights can easily be covered in one day.

Ideally stay a weekend (or even 3 days) enjoying the many museums, water activities and night life of this amazing city.

1 Day in Key West

• Hop on a Key West Trolley Tour for an introduction to the city’s sites.
• Learn more about Hemingway at the Ernest Hemingway Home and Museum .
• Visit the Key West Museum of Art & History .
• Discover Florida’s marine life at the Key West Aquarium .
• Enjoy the street performers at Mallory Square’s nightly Sunset Celebration OR
• Sail into the sunset on a Key West Sunset Cruise .

2 Days in Key West On a second day:

• Rent a bike to visit more Key West sites.
• Snap a photo at the Southernmost Point of the Continental U.S.A .
• Surround yourself with butterflies at the Key West Butterfly and Nature Conservatory .
• Visit the Harry S. Truman Little White House .
• Enjoy more Key West Museums , such as the Tennessee Williams Museum or the Key West Lighthouse & Keeper’s Quarters.
• Search for the tastiest slice of Key Lime Pie .
• After sunset, experience eerie tales on the Ghosts & Gravestones Tour .

3 Days in Key West With an additional day, enjoy any of these activities:

• Take the ferry and explore the remote reefs at Dry Tortugas National Park .
• Try one of many thrilling Key West Watersports such as Jet Skiing.
• Discover the history and enjoy the beach at Fort Zachary Taylor Historic State Park .
• Soak up the sun at one of the beautiful Key West Beaches .
• Explore the natural beauty of the Tropical Forest & Botanical Garden .
• Enjoy the nightlife and live entertainment at one of the many Duval Street bars.
• Join the excitement at one of the annual Key West Festivals celebrating arts and culture.

Map of Key West Attractions

Key West Must-Sees

Be sure to enjoy these 5 things on your visit to Key West.

Key West Sunset Celebration

Ernest hemingway home and museum, key west museum of art & history, key west aquarium, harry s. truman little white house.

The nightly celebration in Mallory Square has been happening since the late 1960’s.  The civic square has an almost unobstructed view to the west of the Gulf of Mexico and has been known as “the” place to watch stunning Key West sunsets since the 19 th century.

Every night, locals and tourists alike enjoy live entertainment by street performers of many different kinds.  Any evening you could find live music, magicians, jugglers, comedians, stunt performers with high-wire acts, sword swallowing and maybe even cats jumping through hoops.  There are always local artists with paintings, clothing, souvenirs and more. Of course, don’t forget to enjoy the food!

The festivities start about 2 hours before sunset and reach a fever pitch as the sun sets providing a breathtaking backdrop for the vibrant energy of this great street party.

By the way, any cruise ship docked during the day must leave port at least 2 hours before sunset.

Tour Hemingway’s Spanish Colonial home and the studio where the Nobel laureate wrote about 70% of his literary works.  Hear quirky stories about his life, travels, wives and the 6-toed cats.  Tour the gardens and see many supposed descendants of those original cats who still “own” the grounds.  Hemingway lived in the home between 1931 and 1939.  You many want to purchase a Hemingway novel in the bookstore.

For more information, see the Ernest Hemingway Home and Museum website.

HISTORY: The house, completed in 1851, is a US National Historic Landmark.  The Hemingways restored the neglected property and made several additions.  The house was one of the first in Key West to have interior plumbing and the huge in-ground swimming pool was the first in the Florida Keys.  Hemingway owned it until his sons sold it by auction after his suicide in 1961.  It opened as a museum in 1964.

Learn about Key West’s cultural heritage as well as local, national and maritime history over its two floors.  The ground floor houses temporary exhibits showcasing the museum’s vast collection of artwork and historic items on a rotating basis.  Upstairs photographs and artifacts explain the construction of the Overseas Railway, the 1935 hurricane that doomed it, the sinking of the USS Maine during the Spanish-American War, famous Key West residents and more.

This is the perfect place to get a better understanding of Key West’s uniqueness and the diverse influences that have shaped its history.

For more information, see the Key West Museum of Art & History website.

HISTORY:  The beautiful, red-brick building, near the waterfront and Mallory Square, opened in 1891 housing the U.S. Custom House, the island’s Post Office and Federal Courthouse.  In the 1930s, the US Navy took over the building from the Federal government, converting it into office space.  It was abandoned in the early 1970s. The Key West Art & Historical Society realized its worth and, with lots of support from residents and government, the building was restored and re-opened in 1999.  The building is recognized as a National Landmark.

See a wide variety of marine life in tanks of all sizes, both outdoors and indoors.  Tanks are filled with many different species, including sharks, stingrays, moray eels, barracuda, grouper, tropical fish, turtles, conch, sea cucumbers and more.

The aquarium is involved with marine conservation in the Florida Keys.  The Aquarium’s experts introduce some of the residents of the tanks, many of whom are at-risk species.  Learn about efforts to protect and conserve endangered species and others to eradicate non-native species from Florida waters.

For more information, see the Key West Aquarium website.

HISTORY:  The aquarium opened in 1935 after 2 years of construction. It was an open-air aquarium, one of the first in the US.  Unfortunately the 1935 Hurricane wiped out the Overseas Railway and the only land link to Key West 6 months after it opened.  This dramatically affected the number of tourists who could reach Key West and its initial success.  It persevered and survived.  In the 1960’s a roof was placed over the open-air tanks.

Enjoy a guided, approximately hour-long, tour of the building used by President Harry S. Truman during his presidency as his “winter White House”.  Hear interesting stories about Truman’s time in Key West.  Learn how he, his wife and their staff, lived, worked and continued to govern while staying in officers’ quarters turned presidential residence.  President Truman visited Key West for rest and relaxation between 1946 and 1952, using the house for a total of 175 days. 

For more information, see the Harry S. Truman Little White House website.

HISTORY:  The building was built on the waterfront in 1890 to house officers stationed at the U.S. naval base.  Eventually it was converted to house the base commandant and his family.  The house hosted a number of important guests in addition to Truman.  Thomas Edison, worked for the navy during WWI, Presidents William Howard Taft, Dwight Eisenhower, and John F. Kennedy all stayed during their presidencies. Presidents Jimmy Carter and Bill Clinton visited after their terms.  The house continued to be quarters for commanding officers until Truman Naval Station closed in 1974.  In 1991, it opened as a state historic site and museum.

Old Town Key West

Many of the city’s highlights are located in the Key West Historic District , essentially the part of the island west of White Street.  With only a day or two, spend your time in this charming area full of colorful houses, lively bars and vibrant shops.

The buildings are predominantly from the 18 th to 20 th centuries.  A number of museums are in these historic buildings helping preserve its architectural heritage.  The homes are built in “Bahama-style”; one or two-stories built to withstand high winds and most have wrap around porches to shelter windows from direct sunlight. 

Duval Street is the heart of Old Town’s commercial district.  A number of important Old Town buildings are on Duval or in the vicinity.  Full of souvenir shops, restaurants, bars and entertainment venues, Duval’s lively atmosphere is especially so after dark.  Every night is party night on Duval!

A trolley tour is a great introduction to the city and Old Town’s highlights.  If you want to leave the car behind, but don’t want to walk everywhere, consider renting a bike .  On our recent 3-day stay, we did both and it was the perfect mix for us.

More Old Town Attractions

Old Town Key West has many fantastic museums and attractions to explore.  These are worth a look depending on your time and interest.

Key West Lighthouse & Keeper’s Quarters

Climb the 88 steps at the Key West Lighthouse & Keeper’s Quarters for a bird’s-eye view of Key West.

Learn about the maritime history of Key West through the words and belongings of former lighthouse keepers and their families.  Discover the often difficult, now forgotten, life of the keepers.  They kept the light on regardless of the hazards to ensure the safety of ships and sailors.

HISTORY:  This lighthouse opened in 1848 with a female keeper which was unusual for the 19 th century.  Over the decades several upgrades occurred.  A new 3 rd Order Fresnel Lens was installed; the tower’s height was increased; the Keeper’s Quarters were added; and the light was electrified.  In 1969 the lighthouse was decommissioned.  At that time, the Keeper’s Quarters housed a military museum and the tower was opened to the public for tours.  In the late 1980’s the structures were restored to their original designs and the museum re-opened in 1990 in its current configuration.

Tennessee Williams Museum

Explore the life and works of playwright Tennessee Williams at the Tennessee Williams Museum .  Williams, the winner of multiple literary awards, lived in Key West for more than 30 years.  The huge collection of photographs, plays, books, news articles, videos and other artifacts provide visitors with a deep look at Williams’ literary genius.

Tennessee Williams did not live in the museum building.  His first visit to Key West was in 1941 but he returned regularly often staying at La Concha Hotel (now the Crowne Plaza Key West).  He purchased 1431 Duncan Street in 1949 which was his home until he died in 1983.  His former home is not open to the public.

HISTORY:  The museum building was built in 1884 on a spot which was the edge of the city at that time.  Over the next century, the city grew around it so that it is now in the centre of Old Town.  In recognition of Williams’ 100 th birthday a temporary exhibit was held using 513 Truman.  Its success led to the comprehensive, permanent museum seen today which opened to the public in 2013.

Key West Shipwreck Museum

At the Key West Shipwreck Museum learn about the dangerous waters of the Florida Keys and the often life-saving role of “wreckers”.  The wrecking industry led to Key West being the most populated place in Florida and the richest, per capita, in the US during the last half of the 19 th century.  Discover actual artifacts from the vessel Isaac Allerton, sunk in 1856 on a Florida Keys reef, which was rediscovered in 1985.  Climb the 65-foot observation tower to see Key West today and hear the story of the lookouts watching for ships in trouble.

Mel Fisher Maritime Museum

Discover the secrets of the sea at the Mel Fisher Maritime Museum .  See artifacts and exhibits about maritime archaeology and the salvaging work of legendary treasure hunter Mel Fisher.  See some of the discoveries of Fisher and his crews from shipwrecks in the Florida Keys.  The museum was created by Fisher and became a non-profit organization in the early 1990s.

It is a museum, Conservation and Archaeology lab, and research facility.  The museum is open to the public 7 days a week with lab tours offered twice each weekday. 

HISTORY:  The building, built by the US Navy and completed in 1910, was used as a storehouse until the navy pulled out of Key West in the 1970s.  The government initially leased the building to Mel Fisher’s salvage company.  The company purchased it in the late 1980s.  After his death, the Mel Fisher Maritime Museum purchased it from the salvage company.

U.S. Coast Guard Cutter Ingram

Step aboard the U.S. Coast Guard Cutter Ingram , a Maritime Museum and National Historic Landmark.  Learn the history of the Ingram over her more than 50 years of service from 1936 to 1988.  She was stationed around the world carrying out search and rescue, drug interdiction, and maritime defense in both war and peacetime.  Tour the ship and discover what life on board offered.  Her exemplary record made her the ideal vessel to highlight the history of the US Coast Guard.  She is the most decorated vessel in the Coast Guard fleet and the only cutter awarded two Presidential Unit Citations. 

HISTORY: After decommissioning, she was donated and displayed at the Patriots Point Maritime Museum in Charleston, South Carolina. In 2009 she was moved to her current dock on the Truman Waterfront.

Audubon House & Tropical Garden

Step into the past at the Audubon House & Tropical Garden .  The restored house is furnished with antiques from the first half of the 19 th -century.  See orchids, bromeliads, tropical palms and more in the 1-acre garden as well as the outdoor cookhouse.  It is typical of early Key West cookhouses.  The gallery is a registered dealer of Audubon art and Audubon prints.

John James Audubon, a self-taught artist and ornithologist, is famous for his 19 th -century drawings of the bird species of North America.  Local lore says that he visited the property during his Key West visit in 1832, and that the garden is pictured in several drawings of local bird species.

HISTORY:  The house was built between 1846 and 1849 for Captain John Huling Geiger, a harbor pilot, master wrecker and one of Key West’s wealthiest citizens.  It remained in the Geiger family for over 110 years.  It was restored and opened as the Audubon House Museum in 1960. 

Oldest House Museum

The Oldest House Museum showcases Key West and Southern Florida’s oldest house.  The former estate of wrecker Captain Francis B Watlington and his family includes their home, the kitchen house and an exhibit pavilion.  See family portraits, original furniture and the last surviving Southern Florida cookhouse.  Enjoy the peaceful garden at the rear of the house, away from the noise of Duval Street.

HISTORY:  The house has stood at 322 Duval Street since the mid-1830’s.  The original structure, built in 1829, was smaller and located on Whitehead.  It was moved to Duval and expanded for Captain Watlington and his family whose descendants lived in the house until the 1970s.  It opened as a museum in 1975.

Key West Butterfly and Nature Conservatory

This glass-enclosed conservatory is a tropical wonderland, full of flowering plants and trees.  It is the perfect setting to see birds and butterflies from around the world.  There’s even a turtle or two.  The pair of flamingos are only too happy to put on a show.  At the learning center, see the displays about butterfly anatomy, life cycle, feeding and more.  Be sure to check for butterfly travelers when you leave the conservatory so that your only souvenir is from the gift shop.

For more information, see the Key West Butterfly and Nature Conservatory website.

Fort Zachary Taylor Historic State Park

The state park is on the lands formerly Fort Zachary Taylor, the longest serving US Coastal Fortification.  Take a self-guided tour of the fort and then spend the afternoon enjoying its beautiful beach, snorkeling, fishing or paddling nearby.  Snorkeling equipment can be rented at the concession along with chairs and umbrellas.  Bikes are welcome in the park with dedicated lanes and lots of bike racks.

For more information, see the Fort Zachary Taylor Historic State Park website.

HISTORY:  Construction of a 3-tiered fort began in 1845.  It was connected to Key West by a 1200 foot causeway.  The fort was a Union stronghold for the entire American Civil War.  During the Spanish-American War the fort was modernized, a new battery added and its overall height lowered.  The fort continued to be modernized and served during World Wars One and Two.  Its active duty ended in 1947.   Designated a National Historic Monument in 1973, it houses the largest collection of Civil War armament in the world.  The grounds and fort opened as a state park in 1985.

Southernmost Point in the Continental United States

The Southernmost Point Monument is a super-sized, colorful buoy at the corner of Whitehead and South Streets.  There always seems to be people in line for pictures but it moves quickly so don’t avoid stopping here!  The buoy notes that Cuba is only 90 miles away.

Free Things To Do in Key West

The Southernmost Point monument is just one free attraction in Key West. There are many more places in the city to walk and explore.

For a complete list, see our article, 16 Best Free Things To Do in Key West .

Beyond Old Town

While the bulk of the attractions in Key West are in Old Town, there are several outside the historic district that are worth a look if time permits.

Fort East Martello Museum

Discover the Fort East Martello Museum , a Civil War-era fort and citadel, restored to its 1860’s plans.  See artifacts from the Civil War and Key West’s military history, and learn about industries important to the development of Key West, wrecking and cigar-manufacturing.  The metal sculptures of local artist Stanley Papio are on display.  Robert the Doll is also a resident of the museum.

There are two ways to visit the museum.  Enjoy a self-guided daytime museum visit or come in the evening for the Ghost Hunt and Robert the Haunted Doll Experience . On the guided ghost hunt discover the stories of Civil War soldiers and the infamous Robert the Doll. 

HISTORY: Construction began on both East and West Fort Martellos during the Civil War.  While the Union was in control of the city, many citizens supported the Confederacy creating friction between the government and construction workers.  This animosity plus outbreaks of Yellow Fever and a hurricane led to many construction delays.  Ultimately, the forts were abandoned and never fully built.  Due to their strategic location they were used for storage, barracks and radio stations during the Spanish American War and both World Wars.  After WWII, they fell into disrepair and possession was given to the local county.  Fort East Martello opened as a museum in 1951.   Since then extensive restoration work has been done.

Key West Tropical Forest & Botanical Garden

Enjoy the Key West Tropical Forest & Botanical Garden .  Started in 1936, this is the only frost-free, sub-tropical, native-plant, botanical garden in the continental United States.  The over 15 acres of garden and forest includes 2 freshwater ponds and has trails and wide boardwalks perfect for exploring.  See plants in bloom in spring and summer with plenty of birds and butterflies.  Many of the flora and fauna species are considered endangered.  Check out the visitor center, gift shop, plant nursery, sculptures of local artists and much more.

Dry Tortugas National Park

Dry Tortugas, about 70 miles west of Key West, is a great day trip.  Visit the 19 th -century Fort Jefferson, one of the largest forts ever built.  It was never fully armed but was never attacked.  It served its intended role to protect the peace of a young country as part of a chain of coastal forts from Maine to California.  

The park is 100 square miles of open water with 7 small islands.  Its waters are known for the exceptional snorkeling and diving opportunities on coral reefs and shipwrecks.

Garden Key, the 2 nd largest island in the park, is only about 14 acres.  It is the gateway to the park.  The park headquarters, visitor center, campgrounds and Fort Jefferson are all on Garden Key. 

How do I get to Dry Tortugas National Park? The only ways to access Garden Key are by Key West Seaplane Charters , the Yankee Freedom Dry Tortugas Ferry from Key West (run by the Dry Tortugas concessionaire ) or your own private boat.

For more information about park activities and camping, see the Dry Tortugas National Park website.

Key West Trolley Tours

A trolley tour is a great introduction to Key West history and its places of interest.  There are two options:  Old Town Trolley Tours (which we did) and the Conch Tour Train .

Old Town Trolley Tours

The “hop-on / hop-off” route covers the entire island in 90 minutes.  The trolley drivers are trained tour guides who recount the history and stories of Key West, in an entertaining, family-friendly way.  Learn about pirates, playwrights, presidents and much more.

There are 13 stops and riders can hop on and hop off as often as they wish all day long.  Stops are close to attractions, shopping, restaurants and lodging options so pick your stops based on the day’s itinerary.  The first tour leaves Mallory Square, at the front of the Aquarium at 10:00 am and the last one at 4:30pm.  Tours depart at least every 30 minutes. 

For the list of stops, price and to purchase tickets, see the Old Town Trolley Tours website.

Conch Tour Train

Sit back and enjoy a 75-minute tour through Old Town hearing the city’s legends and lore from the expert, friendly staff.  The tour has 3 stops.  Station Depot, 501 Front Street at Duval, is the beginning of the tour.  Grab your snacks in the shops nearby.  (The train stays here for 10 minutes.)

The second stop is Truval Village (around corner of Truman and Duval Streets).  Feel free to disembark, visit the nearby sites then catch a later train to continue the tour. 

The third stop is the Sails to Rails Museum, 901 Caroline St. between Grinnell and Margaret Streets.  End your tour at the museum or grab a later train back to Station Depot.

The first tour leaves Station Depot at 10:15 am and the last at 4:15 pm.  Tours depart at least every 30 minutes. 

For more information, see the Conch Tour Train website.

Ghosts & Gravestones Tour

For a great introduction to the city’s haunted history, and to take a load off your tired feet after a day of exploring, enjoy a 60-minute trolley ride instead of a walking ghost tour.

Costumed guides tell interesting stories about the spirits said to visit some of Key West’s historic locations, such as Captain Tony’s Saloon and Fort East Martello where a doll named Robert resides.  The tour visits the basement and first floors of the Shipwreck Museum for more paranormal stories of experiences in the building and details of a man’s suicide from the top of the building’s tower.  We had a great time being “the doomed” during our tour.

The first tour leaves the Conch Tour Train’s Station Depot (501 Front Street at Duval) each evening at 7:00 pm and the last at 10:00 pm.  Tours depart every 30 minutes.  Reservations are required.

For more information and to book your tour, see the Ghosts & Gravestones of Key West website.

For a haunted walking tour , try the Key West Ghost & Mysteries Tour , a 90-minute walk to the most haunted locations for scary stories and experiences not to be forgotten.

Key West Bike Rentals

Old Town’s small size and the close proximity of attractions, makes two wheels the best way to get around Key West.  There are a several options in Old Town.  Most will deliver your rental to you during business hours.  We rented from A & M Rentals .

Key West Bars with Live Music

Key West is known for its vibrant live music scene.  Some popular Key West bars often host talented musicians and bands, offering a variety of genres such as rock, reggae, blues, and country.

• Sloppy Joe’s – This bar and restaurant, around since the 1930s, was Ernest Hemingway’s favorite hangout.  Enjoy their traditional Sloppy Joe’s sandwich and stay for the live bands on their massive stage.
• Green Parrot Bar – Historic dive bar with friendly local patrons and eclectic live music including blues, rock, and reggae.
• Irish Kevin’s – Lively Irish pub that encourages audience participation.
• Hog’s Breath Saloon – Rustic outdoor bar, serving tropical drinks, with a variety of music genres.
• Durty Harrys – Large outdoor party spot with great rock bands.
• Captain Tony’s Saloon – oldest bar in Key West, the original location of Sloppy Joe’s and a favorite watering hole of Ernest Hemingway, Tennessee Williams, and Jimmy Buffet.

Key West Key Lime Pie

This is considered the official dessert of Florida.  Key limes, which are smaller and grown in tropical and subtropical regions, are more tart than regular limes, giving the pie its distinctive flavor. The dessert is typically made with a graham cracker crust and a creamy, tangy filling. Key West is particularly famous for its Key Lime Pie, and many establishments in the area claim to serve the best version of this beloved dessert.  

These are some of the most popular places to sample Key Lime Pie:

• Southernmost Key Lime Shop : Cute little shop with friendly staff.  We grabbed one of their tasty Key Lime Pies to go.  Sweet and tart.  Excellent.
• Key Lime Pie Bakery : Fresh and tasty pies, variety of flavors and sizes, convenient location, fast service, good value for money.
• Blue Heaven : This restaurant is famous for its Key Lime Pie.  This popular place also has live music in the evenings.
• Kermit’s Key West Key Lime Shoppe : Lots of Key Lime Pie and other types of pies at this touristy shop.
• Key West Key Lime Pie Co .: Pop into this shop to watch them make the pies on site. The crumbly crust of this pie is amazing.  Grab one to go.

Key West Beaches

Beaches are a major tourist draw, as visitors look forward to enjoying the crystal-clear waters of the Key West area.

These are the most popular beaches in Keys West.

Key West Sunset Cruises

One of Key West’s popular evening activities is watching the sunset over the ocean on board a beautiful sailboat.  Cruises may include live music, refreshing beverages, and light snacks.  Passengers relax and unwind enjoying the beauty of sunset on the tranquil waters of the Gulf of Mexico.  Many of the Key West charter companies offer sunset cruises. We used Danger Charters.

Key West Water Activities

A number of companies offer visitors to Key West the opportunity to explore the vibrant marine life and stunning coral reefs in the waters surrounding the island.  Snorkeling, jet ski tours, kayak rentals, dolphin tours are options with many of the Key West charter companies. We decided on a jet ski tour with Barefoot Billy’s Boat Cruises .

Key West Charter Tour Operators

These are several tour operators offering sunset cruises and water activities from marinas around Key West.

Key West Festivals

There’s always something happening in Key West.  Here are some of Key West’s most popular annual festivals.

• Key West Pridefest : A joyful and inclusive celebration of the LGBTQ+ community.  There are lots of parades and parties. (Early June)
• Key Fantasy Fest : This adult-themed festival featuring elaborate colorful costumes has a wild party atmosphere and a great parade.  10-days of fun. (October)
• Hemingway Days : A celebration of Ernest Hemingway’s legacy with literary competitions and of course, a Hemingway look-alike contest. (Late July)
• Key West Songwriters Festival : A gathering of talented songwriters performing their original music across various venues in Key West. (Early May)
• Key Lime Festival : A delicious celebration of Key West’s iconic Key Lime Pie.  There are pie-eating contests and cooking competitions. (1st weekend of July)

Key West Accommodations

Looking for a hotel in Key West ?

Make Old Town your home base while exploring the Key West Historical District. Check out these great options.

• The Gardens Hotel – Amazing!  We thoroughly enjoyed our stay here!  
• Orchid Key Inn – Exceptional Adults-Only property
• Parrot Key Hotel & Villas – Great value in New Town
• Here are other great hotels in Key West .

Florida Keys Road Trip

Key West is just one of the many great locations in the Florida Keys.  Be sure to check out our detailed article, Florida Keys Road Trip , to discover many more places to visit on a one-week journey through the Keys.

Interested in more Itineraries? Sign up here.

(No spam. Just great travel tips.)

Thanks to Florida Keys Tourism for hosting portions of our stay. See the Key West and the Florida Keys website for more Key West inspiration.

Valerie Vanr

Valerie is the Co-founder of AvrexTravel.com. Val enjoys travel photography and writing informative City Walking tours.

The Perfect Weekend in Key West – 3 Day Itinerary

Posted on Last updated: July 16, 2024

Categories USA

If you’re planning a memorable weekend in Key West, you’re in the right place! In this guide, guest author Polly Clover shares the ultimate 3-day Key West itinerary for a fun-filled weekend alongside all of her top tips for visiting.

Disclosure:  Some of the links in this post are affiliate links. If you purchase a product through these links, we will earn a small commission  at no extra cost to you.  And we can continue bringing you free tips and advice. If you found the content helpful and are kind enough to use our affiliates –  you are awesome, and we thank you! 

Weekend in Key West, FL: Day 1

Weekend in key west, fl: day 2, weekend in key west, fl: day 3, other key west activities.

• Where to Eat and Drinkin Key West Florida
• Is 3 Days inKey West FL enough?
• Where to Stay for aKey West Weekend Getaway

3 Days in Key West Budget

Getting around key west, is key west lgbtq+ friendly, when to visit key west, key west tours, enjoy your long weekend in key west.

• Book accommodation on the East Coast with  Booking.com
• Stay connected with a  local e-sim
• Explore the East Coast on a  best-selling tour .
• Don’t forget  travel insurance!

3-Day in Key West Weekend Itinerary

A long weekend in Key West is the perfect opportunity to enjoy nature, relax, and have a little adventure.

It’s easy for just about anyone to enjoy the itinerary below, but it can also be easily adjusted if you want to include anything else or switch some things around. Here’s a quick rundown for each day in Key West:

• Day 1: Hang out on the beach and take a sunset boat cruise.
• Day 2: Visit Dry Tortugas National Park.
• Day 3: Explore the city – shopping, historical sites, dining, and more.

Hang out on the beach and take a sunset boat cruise.

During the day – A day at the beach is the perfect way to start your long weekend in Key West. There are so many gorgeous beaches to choose from, and you really can’t go wrong with any of them.

I would personally pick one beach and settle in for the day. You can also beach hop and visit two or three if you want to squeeze in a couple of beaches.

Here are a few of the best beaches in Key West:

Smathers Beach : offers a picture-perfect sunrise if you’re up for an early morning. It’s also one of the biggest and most popular beaches in Key West. 

Smathers Beach is the perfect spot for families or beachgoers who enjoy activities. There are watersport rentals, including kayaks and jet skis. Beach volleyball is also popular here! 

Rest Beach – If you prefer to kick back and appreciate a low-key beach day, Rest Beach is the place to go. It’s located at C.B. Harvey Park and boasts soft sand perfect for laying out and seacombing. 

Higgs Memorial Beach – Just next to Rest Beach is Higgs Memorial Beach. This beautiful beach is filled with amenities and offers plenty of space for visitors to spread out.

The snorkelling is great here, and it’s an excellent beach for relaxing and enjoying the scenery.You can also find beach rentals if you want to participate in watersports.

Zachary Taylor State Park : The best beach for those looking to get off the beaten path and enjoy nature. It’s home to a pristine beach with breathtaking clear waters that are perfect for snorkelling.

For the Evening: A Sunset Cruise – Finish your beach day with a sunset cruise and enjoy panoramic views of the Gulf of Mexico. From a live music sunset sail  to a buffet boat dinner with an open bar , there are many options for enjoying a Key West sunset from the water.

Visit Dry Tortugas National Park.

During the day – Just west of Key West is Dry Tortugas National Park. While it’s not directly in Key West, I recommend a day trip to this stunning 100-square-mile park. 

This natural wonder is made up of 7 small islands and offers endless outdoor attractions and activities, including historical sites, snorkelling opportunities, and secluded beaches.

To visit Dry Tortugas National Park, you can take the Yankee Freedom Ferry from Key West first thing in the morning, with a check-in time at 7 AM. The ferry arrives back in Key West at 5:15 PM.

The ferry trip and tour will take you on a full-day adventure, with a tour of the fascinating Fort Jefferson and a snorkel adventure in some of the world’s most pristine waters.

The cost for this visit to Dry Tortugas National Park is $190. This includes activities and meals. There are discounts for children, students, active military, and seniors. 

For the evening – If you’re looking for nighttime activities when you arrive back in Key West, here are some noteworthy things to do in the evening:

• Sunset Pier : a laid-back seafood spot on the water with drinks and live music.
• Key West Theater : an award-winning performing art theatre.
• Duval Street : a lively area in Key West with a vibrant nightlife scene.

Related Read

10 Days in Florida – The Ultimate Florida Itinerary

Explore the city – shopping, historical sites, dining, and more.

While Key West is mostly about the ocean and gorgeous views, the city itself is also well worth exploring. In fact, the Old Town area has enough to offer that it’s easy to spend the entire final day of your weekend in Key West here.  Old Town is walkable, and  bicycle rentals  are also available.

During the day – Start the morning at Key West Historic Seaport, where you can discover picturesque views and charming cafes. The  Cuban Coffee Queen  has excellent coffee and serves breakfast all day.

After exploring Key West Historic Seaport, you can make your way to Duval Street. This is the centre of Old Town, or downtown, and Key West’s most lively area. 

I suggest spending your entire day here. There are countless shops, restaurants, bars, and historical sites worth visiting, along with nighttime activities.

For a start on what to see and do around Duval Street, check out these places:

• Truman Little White House: a museum that was once President Truman’s winter home; entry is $22.20 with a discount for children.
• Ernest Hemingway Home and Museum: the stunning historical home of the famous writer Ernest Hemingway; entry is $17 with a discount for children.
• The Tennessee Williams Museum: a fascinating museum for the literary playwright who once called Key West home Tennesee Williams; entry is $7 with discounts for children, students, and active military.
• The Key West Butterfly and Nature Conservatory: a charming butterfly park and garden; entry is $15 with discounts for children, active military, and seniors.
• Mallory Square: a waterfront area that boasts terrific sunset views, delicious restaurants, and a vibrant nightlife scene.

Tip – A free shuttle takes you around the city if you stay at the Dunhill Hotel.  

While the 3-day Key West itinerary above offers a top-notch experience filled with the best local activities, here are some additional noteworthy things to do:

• Join a local bicycle tour .
• Go on a dolphin tour .
• Dive the Vandenberg, a massive artificial reef and iconic wreck.
• Visit the Key West Lighthouse.
• Take a picture in front of the famous anchored concrete buoy, “Southernmost Point of the Continental U.S.A.”

Where to Eat and Drink in Key West Florida

Foodies are in luck on a weekend trip to Key West. There are endless places to enjoy delicious food and drinks during your weekend getaway to the beach.

The restaurants and bars below are all located in the popular Old Town area, Key West’s city centre.

• Breakfast: the breakfast club, too ($$)
• Seafood: Lagerheads Beach Bar & Watersports ($)
• Pub & bar food: Lucy’s Retired Surfers Bar & Restaurant ($$)
• Caribbean-American: Louie’s Backyard  ($$$)
• Tapas: Santiago’s Bodega ($$)
• Cocktail bar: General Horseplay ($$)
• Dessert: Better Than Sex – A Dessert Restaurant ($$)

Tips for a Long Weekend in Key West, FL

With so much to see and do and Key West’s breathtaking scenery, it’s almost impossible not to have an incredible trip. However, the tips below can help you make the best of your Key West weekend getaway. 

Is 3 Days in Key West FL enough?

Three days is absolutely enough time to spend in Key West. The island is small and offers the perfect 3-day vacation experience.

With that said, there’s so much to enjoy that you can easily extend your trip and not get bored.

The 3-day Key West itinerary below takes you on a journey to experience the best of this fantastic island – nature, history, scenery, and food.

Where to Stay for a Key West Weekend Getaway

Although Key West is a small island, running 4 miles long and about 2 miles wide, there are several distinct areas to stay. 

I personally recommend staying in Old Town, also referred to as the Historic District or Downtown. This is where the popular Duval Street is, complete with shops and restaurants. 

Beachside is also a great area to stay. Located along the island’s southern shore, it’s close to many of the popular beaches. 

You can compare all accommodation options in Key West here or by using the map below:

Your weekend Key West budget will vary depending on your travel experience, but most travellers can plan to spend between $380 and $500 per day. This includes accommodation, transportation, meals, and activities.

Key West is considered a paradise vacation, and with that comes high prices, so it’s easy to splurge. However, there are ways to visit on a budget. Here are some affordable ways to enjoy 3 days in Key West:

$ – Go during the off-season: June through November.

$ – Book accommodation outside of the city centre.

$ – Enjoy picnics at local parks.

$ – Check out free activities, including a self-guided tour, Key West Wildlife Center, watching the beautiful sunsets, and hanging out on Higgs Beach.

$ – Save on transportation and stay in Old Town, the walkable, lively area of Key West.

One of the best parts about a vacation in Key West is how easy it is to get around. Keep in mind that the island is only 8-square miles, so just about everything is close together.

Popular forms of transportation in Key West include cars, bicycles, and walking. There are also taxis, moped rentals, city buses, pedicabs, and hotel shuttles.

It is! Key West is known for its safe, relaxed, and welcoming vibe. Many travellers, including the LGBTQ+ community, love visiting this carefree Florida island.

The Key West Business Guild is dedicated to encouraging LGBT travel to Key West. They work to promote special events, support gay-owned, gay-managed, and gay-friendly businesses, and strengthen the gay community’s position within the local community.

Be sure to visit Duval Street between Angela and Petronia Streets for a fun time! This neighbourhood is home to some of Florida’s most lively gay bars and clubs.

Gay Travel – 39 Safety Tips for LGBTQ+ Travellers

Key West is a paradise all year long. For affordability, fewer crowds and the best weather, visit in late spring or early summer.

Many snowbirds head to Key West during winter to escape the cold. Because of this, you’ll find more crowds and higher prices. That said, winter offers amazing weather in Key West – sunny days with temperatures in the 70s.

From late spring through the end of summer, you’ll find that snowbirds have headed home, and spring breakers and summer vacationers are visiting Key West. Naturally, this brings a fun atmosphere but again higher prices.

Fall in Key West brings the rainy season, so you’ll find fewer crowds and lower costs. Although, the weather during this time is hit and miss. 

If you can plan a last-minute trip depending on predicted weather, fall can be a great time to enjoy a long weekend in Key West for pleasant weather and fewer people.

Sometimes, the best way to experience a new place is to take a guided tour. 

Not only does it take all the stress out of planning, but you get to learn a lot more about the area than you would when exploring alone.

We always use Get Your Guide  when we book tours. They have a diverse and unique selection of tours in locations all over the world, including Key West. Check them out!

I hope this 3-day weekend in Key West itinerary has you excited for an unforgettable vacation to this beachside paradise!

If you’ve visited Key West and have something to add to the list, feel free to share in the comments below.

Planning a trip around the US?

Check out our USA series  for more travel tips and advice. 

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The Perfect Key West Vacation: What To Do, Where To Stay, & More

Famed for pastel conch-style houses, nightlife, beautiful water, and its “renegade attitudes and good times”, Key West is one of the iconic American long weekend trips.   So whether you fly in directly or roadtrip down from Miami along the Overseas Highway, I’m giving you a jam-packed list of the best things to do in Key West!

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A little bit about Key West, Florida

Located at the very southern tip of the Florida Keys, Key West is a 2-mile by 4-mile island (key) connected to the other Keys and the Florida mainland by the Overseas Highway.

It was discovered by Ponce de Leon and claimed by the Spanish in 1513.  The historical fact that kind of blew my mind is that Alabama man John W. Simonton bought (BOUGHT) the island for $2,000 in 1821 and it was then claimed for the United States as part of ceded territory from Spain.

It boasts quite a lot of great pirate and military history (somewhat related to each other), has enjoyed close relationships with both U.S. presidents and many famous writers, and attempted to secede from the United States in the 1980s.  For such a tiny place, it packs a big punch!

Today it makes for a great getaway, whether your interest is history, booze-fueled nightlife, or snorkeling along barrier reefs and enjoying its year-round sunshine.

Other Florida Keys adventures for your trip!

Where To Stay In Key West: Review Of H2O Suites

Two of the Best Sunset Spots in Key West (That Aren’t Mallory Square)

The Ultimate Florida Keys Road Trip Guide

Ranking the Best Key Lime Pies In The Florida Keys

A Spe-“Shell” Experience…Touring The Florida Keys Sea Turtle Hospital

Exploring Bahia Honda State Park: A Must On Any Keys Roadtrip

Florida Keys Brewing Company: A Must-Stop On A Keys Road Trip

John Pennekamp Coral Reef State Park: Is A Short Visit Worth It?

Where to Stay in Marathon:  Grassy Flats Resort Review

Exploring Historic Fort Jefferson In Dry Tortugas National Park

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Where to stay in Key West

My recommendation would be to stay somewhere central, where you can park your car.  Then you can walk, bike, or Uber wherever you need to go.  I stayed in two different hotels while I was there, so here are a couple good places to stay in Key West.

For a bit of a splurge stay, I recommend H2O Suites .  As you can see from the pics below (& check out TripAdvisor reviews ), it’s beautiful and peaceful, and you get your own little private pool!  I booked the Premier Luxury Suite with Private Pool, and the room was large with a separate seating area.  The staff was very welcoming and the shared hotel areas were lovely as well.

The one downside was that since I was only staying one night, my pool never really got full sun during the hours I was there (check-in mid-afternoon to check-out late morning).  But for people who like to go for a dip whenever they feel like, and have it to themselves, this is perfect.

Read my deep-dive review of H2O Suites here!

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The other place I stayed was the Kimpton Ella’s Cottages ( TripAdvisor reviews ), and it was really cute and has strong Key West aesthetic vibes.  I’d wanted to stay at Kimpton’s Winslow’s Bungalows (Kimpton has five small properties spread throughout Key West), but they were sadly sold out while I was there.

The lady at the front desk was super helpful and welcoming, and the property is beautiful.  The room itself is quite small and simple and the walls were pretty thin.  I love this little porch, perfect for sitting with a cocktail in the heat of the afternoon, with the fan blowing on you.  They do have a small pool area and patio as well.

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Some general tips for your Key West vacation

First, let’s talk about logistics and getting around…

• Parking in the main parts of Key West can be a real challenge—both to find, and then it’s super expensive when you do find it (like $4-5 an hour, whether lot or street).  You’ll usually pay by an app on your phone.
• Because of this (and traffic being a pain in the ass), as I mention above I recommend finding a centrally-located hotel where you can park, then walk, bike, or Uber/Lyft.
• If you’re just visiting Key West, I don’t think you need a rental car.  If you’re exploring the Keys overall, you do.  For renting a car, I always search in a few different places and compare both the prices and specific offerings/benefits.  My go-to’s are  DiscoverCars ,  RentalCars.com , and  AutoEurope  as well.
• There’s also a free Duval bus that goes around every 15 minutes or so (10a to midnight usually), so you can stay a bit further away and take that as well.
• Key West is extremely pedestrian-friendly , but still just be careful when crossing the street.  I know that sounds like a “duh”, but after a few cocktails I’ve seen people do dumb things.

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And then here are some miscellaneous tips that may help:

• While parts of Florida are known for gorgeous white sand beaches, the Keys are different.  They’re formed atop coral reefs and so don’t have traditional sandy beaches .  I’ll share what I think are the best beaches in Key West below, but if you’re looking for an amazing beach experience then Key West may not be the best destination.
• There’s a ban on plastic straws here, so I recommend you bring your own reusable metal ones .
• One thing I appreciated was that a lot of of the live music and nightlife starts pretty early , so if you’re wanting to make a decent night of it but not be out til the week hours of the morning, it’s totally doable.  You can watch the sunset, have a great dinner, hit a couple bars or live music spots, and be in bed by 11:00 or midnight.
• In case you were wondering, you CAN drink on sidewalks and walking around.
• Like…literally everything is named “southernmost” .  Make sure you know which one you’re looking for before calling an Uber or booking.

This sounds kind of weird, but you need a midday strategy .  Like, that afternoon time from, say, 2pm to close to 5pm, when it is brutally hot and the lighting is terrible for pics.  Yes, you can lay out on the beach or at the pool but it is wicked hot.  You can siesta.  You can find a bar with decent AC for some day drinking.  But think ahead on this.

Related to that, you’re going to be doing a lot of walking and the heat, humidity, and sun here are no joke .

• Make sure you bring plenty of sunscreen (here are my faves for travel ) and hydrate super well!
• Comfortable shoes are a must…these are my absolute favorite (cute) walking sandals for this type of trip, with loads of cushioning and never any blisters.  I also found thigh glide super helpful to prevent heat rash on my inner thighs.
• I have a detailed post on packing for this type of hot weather beach/pool trip, with everything from my favorite swimsuits to beach coverups to sandals, beach bag, sunglasses, and much more.

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Some of the best things to do in Key West

I’m giving you some of my favorite things to do here, including mentioning a few towards the end that were fine but skippable—I wouldn’t go out of my way.  At the end of this section I’ve also listed a number of different things that were on my “maybe” list but I didn’t get a chance to try.

Key West has something for everyone, from history and architecture, to rowdy nightlife or just basking in the sun at the beach.  It goes without saying that you should pick and choose what appeals most to you.

Explore the downtown area & Duval Street

Duval Street is the epicenter of Key West’s vibe, including its well-known nightlife.  Lined with tons of restaurants and shops (and, thankfully, trees for shade!), every visitor needs to spend some time walking up and down the street.

At night it is HOPPIN’, with tons of bars, loads of live music, and basically whatever nightlife you’re looking for.  Swing by Sloppy Joe’s Bar, opened in 1933 and designated a National Historic Landmark.

Walk down the street and listen for a musical style that fits what you’re looking for.  You’ll see plenty of bachelor and bachelorette parties swarming as well (that’s the scientific animal kingdom term, a “swarm of bachelorettes”…).

During the day it’s still busy, but definitely more chill.  My one complaint was that I wished there’d been places to sit and drink your coffee or eat a takeaway slice of key lime pie.  Give me a bench!

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A special shout-out goes to the bars and live music in Key West.  I intended to see more live music, but was honestly tuckered out after long days of heat and 20,000+ steps.  Whether it’s a solo acoustic guitar, a jazz quartet, or a full band, seeing some live music here is a must!

Some of the places you’ll see recommended the most are Sloppy Joe’s, Green Parrot Bar (blues), Smokin’ Tuna Saloon, Virgilio’s (jazz) and Captain Tony’s Saloon.  But also just walk up and down the main streets and listen…you’ll find a style of musician that will pull you in.

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Try all the key lime pies

I made it my mission on my Keys roadtrip to find the best key lime pie in the Florida Keys.  And 15+ different pies later , I feel pretty good about my success.

The origins of Florida’s state pie date back to the 1800s, and it’s one of America’s iconic desserts.  Traditionally it only has six main ingredients, but the execution and end result can vary widely.  I had a whole list of different places I wanted to try, and while I didn’t get to all of them, I put quite a dent in the list!

My ultimate #1 wasn’t in Key West, but there were three Key West spots in my “cream of the crop” grouping.  I definitely recommend Pepe’s  Café , Banana Café , and Kermit’s Key West Key Lime Shoppe .  And while it looks impressive, Blue Heaven’s famous Mile High version (below) was middling at best, IMO.

See my detailed ranking of the best key lime pies in the Keys

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Take a sunset sail

I love boats and I love sunsets, and combining the two is one of the best things to do in Key West.  As I was planning my Key West itinerary, I knew that having a strategy for sunset each evening was a must…everyone talks about the sunsets here.  And while I didn’t get an epic sunset either night, my sunset SPOTS were primo.

As I was looking for sunset sail companies, I wanted to avoid a big crowded boat and a party atmosphere—we are all about CHILL here on this site.  I also wanted more of a traditional sailboat experience (there’s an intimacy and visceral “on the water” feel), rather than a giant yacht or catamaran.

After looking through a number of options I decided on the Danger Charters “Wind & Wine” tour (you can also see it on Viator ).  They are the rare five-star tour company on TripAdvisor, and also offer a variety of eco tours and on-the-water nature-based adventures, including snorkel and kayak tours.  Their boats are 65-foot schooners designed to replicate the classic skipjacks used in the Keys in the 19th century.

I also loved the wine and hors d’oeuvres aspect of this particular tour…we tried 8 different wines throughout our sail, and they were actually good and interesting rather than just cheap alcohol.  There was a sparkling rosé, a Torrontes, a Pinot Grigio, Chardonnay, Pinot Noir, Merlot, Bordeaux, and a Cabernet Sauvignon.  I definitely recommend!

You can read more about my sunset sail (including some video) here!

A Florida Keys roadtrip was on my list of   where to travel in 2022 !

Or, watch the sunset from Fort Zachary Taylor’s beach

If you’re a landlubber and a boat’s not your style (or you’re just looking for a different experience), I strongly recommend heading to the beach at Fort Zachary Taylor State Park.  More on the park and the beach in a few minutes, but from a Key West sunset standpoint it’s a winner.

The rock wall here is considered by many to be the best place to watch the sunset in Key West (and I agree, it’s especially romantic), but there is a super long stretch of land that looks out toward the sunset so no one needs to fight for space and you never feel crowded.

As you can tell, I was actively staying away from the Mallory Square sunset celebrations just due to personal preferences, but I’ll speak to that a bit later.

Read more about this sunset experience (including some video) here!

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Go on a coffee walkabout

This is one of my favorite things to do in some cities where the coffee is a big draw (like Istanbul’s Beyoglu neighborhood).  And BOY, Key West qualifies!  Specifically, the area is famous for its plethora of delicious Cuban coffee, and I tried to sample as much as I could.

Both mornings in Key West I went around and uber-caffeinated in my pursuit of the best coffee spots.  First stop was the iconic Cuban Coffee Queen at their original Margaret Street location (with the beautiful mural).  I got the cortadito (which became my go-to on this trip).  In fact, I got two of them…because why not??

Another big winner that was more unique was Keys Coffee Company , right on Duval Street.  They have a frozen café con leche here that is DELICIOUS.  It’s not like fully thick slushy frozen, but is just the perfect amount of icy, sweet, strong…truly amazing.  I went back multiple times because I couldn’t get enough.

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Wander around and enjoy the unique charms of Key West

Key West is a great city to explore on foot (or bike), with a very up-close, residential feel…think shaded sidewalks, profusions of flowers, and charming balconied houses (called “Conch House style”).  If you only drove around, you’d miss the heavy doses of quirk and many unique, small beautiful details that pop up around every corner.

If you want a more official walking guide, check out this one from GPSMyCity or join a free walking tour, but I enjoyed just wandering.  I had a handful of sights I wanted to check out, but also just walked up and down little side streets that looked cute.

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Key West also boasts many interesting historical buildings, from the Custom House to the Ernest Hemingway House, Oldest House Museum to the Audubon House.  You’ll see historic markers scattered throughout town and can explore on your own or join a tour geared toward the historic side.

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Catch some rays on the best beaches in Key West

As I mentioned earlier, the Keys are not known for their beaches, at least not in the traditional gorgeous powdery white sand way.  But there are a few decent beaches in Key West and of course the water and sun are awesome.

I’ll show a couple of your best choices below, though I didn’t get a chance to visit Dogs Beach or South Beach so can’t speak to those.

Smathers Beach is a bit further from downtown Key West, but might be #1 or #2 for sunbathing and water sports, and has pretty nice sand (tied with Fort Zachary Taylor on all counts).

It has these lovely tiny boardwalk paths onto the beach that also make a great photo.  There are public bathrooms and showers, watersport rental options (and chair/umbrella rentals), and sometimes there are food trucks.

I swear by my (totally affordable) prescription snorkel mask…here’s where I got it!

Not a beach necessarily, but something to mention briefly (as I walked from Smathers to Higgs)…right near Higgs Beach is White Street Pier, also known as Edward B. Knight Pier.

During the day this isn’t really anything to see, but I heard that sunrise from White Street Pier is awesome.  I intended to check it out but was so tired I never got out for sunrise.

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Then you have  Higgs Memorial Beach Park , also on the southern coast of Key West and a bit closer to downtown.  This beach is smaller, with White Street Pier on one side (so it’s also beautiful at sunrise) and a small pier or break wall on the other (where there’s supposed to be decent snorkeling).

There are quite a few amenities here, including a restaurant, children’s playgrounds, a dog park, tennis and volleyball courts, bathrooms, and showers.  One interesting aspect as well is that there’s both an AIDS memorial and an African refugee cemetery, both right around or just after White Street Pier.

Higgs Beach was okay, but for a beach experience I’d personally do Smathers or Fort Zachary Taylor State Park before this one.  And speaking of Fort Zachary Taylor…

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Combine beach & history at Fort Zachary Taylor State Park

Speaking of beaches, Fort Zachary Taylor State Park provides a two-fer…a cool historical fort plus one of the better beach options in Key West.  Add to that the great sunset views I showcased above, and you’ve got a perfect half-day in your Key West itinerary.

The park is located on the southern edge of Key West, and you can get there by car, bike, or on foot (I took an Lyft there and walked back).  Something to be aware of is that, while the park closes at/after sunset, the fort and all amenities, bathrooms, concessions, etc. close at 5:00pm.  You can learn more about hours and entrance fees here .

The water at the beach is crystal-clear and it has interesting marine life, making it great for beach snorkeling, paddling, and scuba diving.  You can rent snorkel equipment in the park, and they have bathrooms, showers, and a café.

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And then there’s the fort itself.  It predates the Civil War and is a National Historic Monument in its own right, boasting the largest cache of Civil War armament in the world.  It’s worth a little of your time, especially if you’re not getting out to Dry Tortugas.  But it doesn’t hold a candle to Tortugas’ Fort Jefferson …more on that in just a second!

The park also supposedly has great biking and hiking trails, but I didn’t get a chance to check these out.

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Take a day trip to Dry Tortugas National Park

This is one of the things I absolutely think you need to do if you’re visiting Key West.  Dry Tortugas National Park is one of the most remote U.S. national parks, about 70 miles west of Key West and 150 miles south of the U.S. mainland.  It’s also 100 square miles of water, with seven tiny islands in it.

The vast majority of people who visit Dry Tortugas do it as a day trip from Key West, either by sea plane or ferry, and so they get to explore Fort Jefferson.  When I visited, I did it on a private charter sailboat as part of a multi-day sailing trip, so got to see some other parts of the park (like stunning Loggerhead Key ).

Fort Jefferson was built in the mid-1800s to protect the U.S.’s gateway to the Gulf of Mexico (as shipping was king), and it’s the largest all-masonry fort in the U.S.  It is SO much cooler than Fort Zachary Taylor.  Plus, it takes up basically the entirety of Garden Key, so it has gorgeous views out over the water.

Read more about visiting Dry Tortugas & Fort Jefferson!

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The logistics of building a massive fort out in the middle of the ocean in the 1800s is…mind-boggling.  And sadly, by the time the fort was completed, it was obsolete.  It was built over 20+ years with the height of technology, but right in the midst of the U.S. Civil War (1860s) military technology made some leaps (including the rifled cannon), and the fort no longer could compete.  It never saw action.

It’s really beautiful, with lots of decorative brickwork and over 2,000 arches.  Yes, you read that right!  I was kind of obsessed with the way the arches stacked infinitely.

You can see how to plan your visit to Dry Tortugas at the official national park website .  Both the ferry and seaplane sound cool, but to me the seaplane would be the clear winner.  One thing to note, there is no cell signal out here, so plan ahead for that.

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See the southernmost point in the continental U.S.

One little corner of Key West that’s nice to stop by is the buoy marker for the southernmost point in the continental United States.   Yes, it’s kind of cheesy and touristy, and no, I personally wouldn’t wait in line to take pics.  I managed to catch it uncrowded on an early Sunday morning run.

From here, you’re only about 90 miles away from Cuba…the joke you’ll hear is that you’re closer to Cuba than a Walmart.  And it’s 100% true, because Key West is more than 120 miles from the nearest Walmart 🙂

Just a few steps away is the gate to Southernmost Point Guest House , a beautiful and unique old house that’s a hotel now, and makes for a pretty photo shot on a blue sky day.  It was on my shortlist of possible hotels, and I chatted with a lady who was staying there who loved it.

You’ll find that seriously everything is called “Southernmost” (it’s a bit like Peachtree in Atlanta), so make sure you know exactly which one you want if you’re getting an Uber, looking on GPS, or booking a particular hotel.

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Play pirate at Key West First Legal Rum Distillery

One of the few *indoor* things I found to do in Key West was a rum tasting at Key West First Legal Rum Distillery .  You can taste different rums, buy all the different ones they offer, or get a cocktail instead (their piña colada was delicious!).

I spent a half hour trying a few different rums and grabbing a couple small bottles to take home.  Supposedly they offer free tours as well from 11am to 6pm, which take around 20 minutes.  No one offered when I walked in and I didn’t feel like asking.

You can also take a tour or cocktail class at Hemingway Rum Company’s Papa’s Pilar Distillery , named after his beloved boat from what I can tell.

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Sunset Pier & Mallory Square (fine but skippable)

After a loooong and hot day of walking, I ended up at Sunset Pier, so stopped for a cold drink and some shade.  It’s not anything special, but the drink was fine.  It would have a good sunset view as well.

Just around the corner (to the left if you’re facing the water) is Mallory Square.  This spot is famous for its nightly Sunset Celebration, a street festival that happens leading up to the sunset.  There are food vendors, local artists, street performers, and more.

Everyone says this is one of the best things to do in Key West, and I can’t necessarily argue as I haven’t done it.  Crowds aren’t really my thing, but if you do decide to do this, it’s recommended to get to Mallory Square an hour or two before sunset to secure a good spot by the water and enjoy the festival atmosphere.

See my reco for best sunset spots in Key West!

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Snap a pic at Mile Marker 0 (skippable)

US 1 stretches down the entire East Coast, from Maine to the tip of the Keys.  This is its termination point, and only takes a second to snap a fun pic and move on.  There’s typically not a long line here, either (which isn’t often true of the Southernmost Point marker.

See the famous Kapok Tree (skippable)

Native to Central American rainforests, this cool-looking tree is just down Whitehead Street from Mile Marker 0, so it’s easy to walk by for a glimpse.  You’ll probably see some of Key West’s ever-present roosters boppin’ around as well.

There were several items on my list of what to do in Key West that I didn’t get around to doing, either due to logistics or prioritization.  These include:

• A snorkeling trip (I’d hoped to do one closer to mid-Keys, but the weather didn’t cooperate)
• Take a walking food tour or craft cocktail crawl or cocktail class ; I really wanted to do one of these, but the days and times just didn’t work out (or they were booked up)
• Kayaking eco tours of mangroves, or dolphin eco tours on a boat
• Hemingway Home and Museum – I’m not a museum person so wasn’t too sad to miss it, except for the polydactyl (six-toed!) cats.  My coworker told me this is “a must for cat ladies” which cracked me up.
• Butterfly Conservatory – The highlight is apparently the flamingos, not the butterflies…and the great gift shop, which has local art and souvenirs for a good price.
• Key West Lighthouse
• Key West Cemetery
• West Martello Tower

Where to eat in Key West

Oh man, where to start…I already mentioned the great Cuban coffee spots above, so won’t go into that as much here.

One great spot for breakfast or lunch (not sure on dinner) was Banana Café .  I had a delicious veggie crepe with beets, asparagus, caramelized onions, goat cheese, and avocado, and as I mentioned above their key lime pie was in my top-five for the entire Florida Keys.  My breakfast and key lime pie at Pepe’s  Café was also great.

And a shout-out to Key West Cuban Coffee , which had a fabulous menu.  I’d already eaten a bunch and so didn’t get to try their arepas or the other delicious things on their menu.  I got an iced espresso/cortadito and guava and cheese empanada, but the coffee had WAY too much granulated sugar in it to be drinkable.

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I tried to go to Blue Heaven but the wait was too long…however, the hostess told me I could go around the corner to their indoor bar area and get a seat right away.  I did so, and had a decent fresh fish meal along with a mojito and their famous “mile high meringue” key lime pie (which I wasn’t a fan of).

Dinner was a bit uneven for me both nights, mostly because I didn’t plan ahead and make reservations and I’m not willing to wait more than like 15 minutes for a seat.

My first night I ended up at  Moondog Café , where I devoured the Frenchman burger, truffle fries, and sweet potato fries with lime curry sauce while sipping their peach basil sangria.  Generally speaking everything was great.

My second night I ended up at Tiger Bar .  It’s definitely unique.  They have an interesting wine menu (I got the Lambrusco) and no real cocktails.  It’s a limited small plates menu, with some fascinating dishes (but a number that I couldn’t eat).  I tried their tea-deviled eggs (delicious and interesting), beef tartare (good but hot, my favorite), Korean fried chicken (delicious but spicy), and lamb ribs (great flavor but fatty and hard to eat).

One other thing to mention is that a stop for ice cream at Flamingo Crossing is a must!  I tried the strawberries & cream and Cuban coffee flavors and both were great…I wish I could have tried more.  One note, it’s cash-only.

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Wowza, that was a lot!  But as you can see, there are so many things to do in Key West and it makes a great short vacation.  I recommend pairing it with a bigger Florida Keys roadtrip , which is what I did…I spent two days in Key West and then another 3-4 days exploring the rest of the Keys, and absolutely loved it.

Other U.S. long weekend explorations you’ll love:

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Where To Watch The Sunset In Key West: The Two Best Spots That AREN'T Mallory Square

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Old Town Trolley Tours Key West 4.4

Ultimate Key West 3-Day Weekend Itinerary

Nothing is more thrilling than the prospect of a long weekend around the corner. Since the two most prominent holidays that feature that most welcome Monday off, Labor Day and Memorial Day, occur in the warmer months, visions of outdoor grills, swimming pools, and chilling hard on the old Barcalounger are among the most desirable. However, if you decide you want to level up from the common ‘staycation’, there’s an island situated in the southernmost reaches of the Sunshine State that has been delighting visitors for decades. With its pioneer spirit, off-the-grid appeal and beach town charm, Key West is your ticket to adventure!

See the Best First with Old Town Trolley Tours

Our friendly and knowledgeable conductors will take you on a fully narrated journey filled with humor and history as you explore the must-see sights of the Conch Republic. A really handy, time-saving component built into the tour is the freedom to hop on and hop off at any of the 13 stops we service. This means you can take as much time as you like strolling along famous Duval Street with its plethora of bars and restaurants then continue your journey when the next trolley shows up! This entertaining spin through the heart of sunny Key West includes highlights such as the Historic Seaport , Simonton & Greene Streets in the city’s Old Town, Bahama Village, and the East Martello Fort to name just a few.

Pepe’s Café – This Caroline Street mainstay has been feeding locals and visitors since cars still looked like horseless buggies. For all you purists out there who want to sample the traditional recipe that gave rise to it all, Pepe’s pies are the real deal.

The Southernmost Point

Audubon House

El Meson de Pepe – All this Key West adventuring is bound to work up an appetite, so grab a bite, or two, of some of the very best Caribbean delicacies in all of the Conch Republic at El Meson de Pepe. Located in the heart of Key West in historic Mallory Square, this legendary eatery is always buzzing with the rhythms of the other island, just 90 miles away. You’ll delight in all the classics of the Cuban kitchen with a distinctly Key West twist for a culinary experience you can only find here.

Key Lime Pie

You’re on vacation, so put the breaks on that diet and indulge in one of the island’s most delectable creations. This local favorite has a luscious custardy texture, but eats like a cheesecake. The tart, pleasing essence of the Key Lime, with a dollop of freshly whipped cream, makes this a treat all its own. Here are the best places to get your piece of the pie:

Kermit’s Key West Key Lime Shoppe – For over 20 years, Kermit Carpenter and his sister Anita have been making quite a name for themselves with their take on this local specialty. Don’t forget to try their signature creation: a frozen slice skewered on a stick and dipped in dark Belgian chocolate. They also feature a gluten-free version of their tasty pies. Yum!

View this post on Instagram It wouldn’t make sense to celebrate #NationalPiDay without grabbing a slice of some world famous Key West Key Lime Pi(e) from our local favorite pie shop, @kermitskeylime ! 💛💚 ••• 📸: @katherinealice A post shared by Mallory Square (@mallorysquare) on Mar 14, 2019 at 10:21am PDT

Explore Mallory Square & Watch the Sunset

When in Rome, it’s the Trevi Fountain. When in the Conch Republic, it’s Mallory Square . This is the perfect end of day for any Key West adventure. This large promenade, extending out from the water’s edge, is a hub of activity surrounded by some of Key West’s most iconic attractions and shops. Soak up the atmosphere in the Sponge Market, explore the island’s roguish past at the Key West Shipwreck & Treasure Museum and, of course, take part in a long-held tradition by attending the Sunset Celebration where hundreds gather, among colorful street performers and local artisans, to salute the sun as it recedes into the sea.

View this post on Instagram Nature paints with all the colors of the rainbow. 🎨 #MallorySquare #SunsetCelebration 📸: @sarah.robich . . . . . . . . #florida #sunshinestate #lovefl #visitflorida #tropical #floridakeys #keywest #islandlife #paradise #relax #travel #explore #workhardplayhard #travelgram #wanderlust #conchrepublic #discover #vacation #fun #sunset #sunsetlover #waterfront #ocean #color #nature #celebrate #sunsetcelebration #tourist A post shared by Mallory Square (@mallorysquare) on Aug 9, 2019 at 10:04am PDT

Brunch Spots

Blue Heaven – This Bahama Village gem infuses all the best Key West cuisine is known for with their in-demand brunch. Dig into a version of a Low Country classic like pink shrimp and grits or a fluffy stack of scratch made blueberry pancakes; and definitely leave room for the homemade banana bread and decadent Lobster Benedict with Key Lime Hollandaise! The mimosa menu itself is something to behold with an incredible variety of this brunch staple; and they’re not shy with their pours either!

Moon Dog Cafe – This Whitehead Street favorite serves up good food as well as good vibes. This place is renowned for its baked goods, so if your appetite is craving tartlets with fresh fruit, fresh baked breads or mouth-watering mini quiches, look no further. They also boast one of the few menus in the area that is vegan and vegetarian friendly.

Truman Little White House

View this post on Instagram We love our #TrumanKeyWest adventure patch! 🇺🇸 💙 What’s your favorite #TrumanKeyWest souvenir? 📸: @jessdev081 A post shared by Truman Little White House (@trumankeywest) on Aug 6, 2019 at 9:15am PDT

Key West Butterfly and Nature Conservatory

Late Lunch at Fisherman’s Cafe

Located on the banks of the historic Key West Seaport where local fishermen can be seen unloading the day’s catch, this local joint is a must-eat! With seafood so fresh , it practically walks its way to your plate, this fourth generation family of ‘Conchs’ serves up the freshest, most delicious lunch on the island. Try the Lobster Enchilao taco’s, healthful salads and ceviches and local, sustainable fish prepared every way imaginable!

View this post on Instagram Perfect day to enjoy our patio. 🎣☀️| 📷: @joelle_deroche A post shared by Fisherman’s Cafe Key West (@fishermanscafekw) on Jun 12, 2019 at 9:35am PDT

Key West Aquarium

Located in Mallory Square since 1946, the hands-on Key West Aquarium is one of the most historic & interactive attractions on the island. This is a great place to experience the fantastic indigenous marine life that inhabits the offshore ecosystem through a window of wonder that enables visitors to interact with rays, sharks and other sea creatures while expert guides explain the hidden mysteries of the undersea realm surrounding the Florida Keys. You can hold a starfish, pet a shark and get up close and personal with many other aquatic species. Visitors of all ages will enjoy this deep dive into nature.

View this post on Instagram This is how we #fishgape when we #Gram! Happy #NationalAquariumMonth! 🐠🦈🐢 A post shared by KeyWestAquarium (@keywestaquarium) on Jun 3, 2019 at 8:14am PDT

Key West Ghost Tour

Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America. This and more await you on a Key West ghost tour .

Duval Street at Night

Old Town Key West’s main thoroughfare was named after Florida’s first territorial governor, William Pope Duval. If Old Bill were alive today, he would be very pleased with the notoriety the street of his namesake has earned. For a night out on the town and to immerse yourself in the nerve center of this unique town, Duval Street can’t be beat. Here are a few of our top picks for your Duval Crawl:

The Smallest Bar in Key West – With all the bigger-than-life bars on the Duval strip, it’s only right to visit the smallest bar in Key West! This 72-square-foot saloon does not disappoint. Beside their diminutive stature, their claim to fame are their rum runners, said to be the very best on the island. Order at the bar and enjoy your cocktail al fresco and watch the people go by.

Nine One Five – It’s a long weekend, so treat yourself. If you’d like to slow things down a bit and take your sweet time to smell the bougainvilleas, this excellent eatery is just the place to wind down with a beautiful bottle of wine. The menu here is known for its inventive Asian-inspired fare and luxurious, house-made pastas. Located inside a breathtaking, two-story, Victorian home complete with gingerbread house accents and a white-picket fence, this is a Key West date night destination for the ages!

It’s time to drift away from the mainland and cruise the ocean blue. Depending on your group preferences and itinerary, there are two excellent options we recommend for water activities on your last day in paradise.

Visit Dry Tortugas Aboard the Yankee Freedom III

(Full Day Trip, Advanced Reservations Required)

Located in the middle of the big, blue Gulf of Mexico, some 70 miles west of Key West, the Dry Tortugas is one of the most remote and fascinating national parks in the United States. Featuring the remnants of a 19th-century fort that was once the American Navy’s largest, you’ll get the feeling that you’ve suddenly become a character in the ‘Swiss Family Robinson’ or are on some far flung expedition for National Geographic. Get lost on a pristine, unspoiled stretch of beach or nature watch the spectacular array of seabirds and coral reefs. A truly remarkable experience, the only way to get there is by booking a trip on the Yankee Freedom III , a state-of-the-art, high-speed catamaran that transports you to and from this amazing place daily.

View this post on Instagram Escape the ordinary ☀️ #DryTortugas 📸: @wanderingheartbeat A post shared by Dry Tortugas (@drytortugas) on Aug 7, 2017 at 9:20am PDT

Fury Water Adventures

For those looking to get on the water, but don’t have an entire day to spend, Fury has the adventure just for you! Your long weekend should be long on fun and there’s plenty to be had here with special packages that feature everything from parasailing, jet-skiing, and snorkeling America’s only living coral reef to backcountry exploring, and dolphin watch excursions!

View this post on Instagram Leaving work on Friday like… A post shared by Fury Key West (@furykeywest) on May 31, 2019 at 12:26pm PDT

Now that you’re armed with the ultimate Key West to-do list, it’s your move. Ready…Set…LONG WEEKEND!

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YOUR KEY WEST EXPERTS!

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The Perfect 4 Day Key West Itinerary

We spent an amazing 4 days in Key West. Well, any time in Key West is amazing, right? The Kimpton Key West hosted us for a fun time. We explored all of their properties and tried a few new places for dinner. Along the way, I learned a few things I thought I would share about our Key West itinerary.

First off, let’s talk about planning an itinerary… do it, but don’t overdo it. Leave space in the day for random stuff. You are on vacation, after all, not every second of every day needs to be planned. Plan for an island time experience.

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Getting to Key West

How do you get to Key West? There are really three ways… by car, by plane and by ferry.

A lot of airlines now offer direct flights into Key West. Or, you can fly into Miami International Airport and experience the Key West Road trip. If you have never done this, I would plan it at least once. Plan to make stops along the way. Check out the Everglades National Park, Key Largo, and other cool spots along the overseas highway. Did you know there are 11 National Parks in Florida? Two can be found in the Keys (the Everglades and the Dry Tortugas)

The Ultimate Road Trip from Miami to Key West

Along the Overseas Highway, you will notice everything is marked by mileage, with Mile Marker Zero being in Key West.

Rather take a ferry? Check out the Key West Express.

So… with the ground rules set… let’s see how to explore Key West, enjoy some downtime, AND have an amazing time in just 4 days.

The Beginning

Ok.. we planned this on purpose, we arrived very early in Key West. This meant we traveled with very little sleep, but that’s ok.

Side note, I booked our plane tickets directly with the airline. So, they set the schedule, departure/arrivals, and time for the layover. BUT, their itinerary only allowed for 25 minutes from touchdown to take off on our layover down. Might work, if you aren’t 10 minutes late leaving …. but, we managed to make the connecting flight, so all good. But, next time, I will ensure we have plenty of time between connections.

We always travel with carry-on only. It just makes the trip that much easier. Plus, for 4 days… you really don’t need that much stuff. Once we land it’s straight to the hotel. For this visit, we headed to Winslow’s Bungalows. This Kimpton property is just amazing.

Winslow’s Bungalows

Located at 725 Truman Ave, you are fairly close to everything. If you get tired of walking you can always take an Uber or the free Duval Loop bus. If you are taking a cab from the airport to the hotel, you may want to let them know it’s the Kimpton on Truman instead of Winslow’s Bungalows. The reason is these properties used to be part of the Historic Key West Inns, but now are part of the Kimpton family.

This property used to be the Chelsea House and Key Lime Inn. Kimpton has combined them into one property now known as Winslow’s Bungalows.

Here’s a bit of quick history about the property…..

• It’s named after the famous painter and summer Key West resident Winslow Homer
• Has 3 pools, an outdoor bar, and vibrant gardens
• 85 guestrooms including 2 deluxe suites and is Kimpton’s largest Key West hotel
• The room designs pay homage to the property’s past owners including an Army officer, an Irish steamboat Captain, and a circus performer
• On the property is Maloney House, where the first mayor of Key West lived. He planted an amazing fruit grove that is still used by the hotel today.
• The property has 3 stand-alone bungalows to accommodate guests wanting a bit more privacy
• The property is very pet friendly. They offer Henry’s dog treats to their dog guests
• If you want to try the famous Key West bagel made by Goldman’s, they are offered at breakfast (they are very very yummy)
• Music is played at the pool bar
• The old Blue Parrot Inn is across the street and is now part of this property. They have 11 rooms and their pool is called the serenity pool because they don’t play music and it offers a zen tranquil feeling

They didn’t have our room ready yet, remember we arrived early (before checkout). But, that was ok. They held our luggage so we could head off to have breakfast and a much needed cocktail to start the vacation off. Our breakfast of choice? Blue Heaven of course.

After breakfast, it was time to head back to the hotel and enjoy a bit of pool time. Best way to cool off and refresh after a day of traveling.

As you can see, our room was, perfect. Winslow’s Bungalows offers great spaces to relax and enjoy Key West. Not too far from the heart of Duval Street, this place offers three pools and an amazing pool bar.

Fully refreshed, we head out to explore. First stop… the Mile Zero sign. No vacation in Key West is complete without a picture in front of the Mile Zero sign.

Needing a place to cool off, we then headed over to the Custom House. This place offers rotating exhibits all about Key West and those who influenced Key West. Always a great stop. Some the coolest and best things can be found in their gift shop.

Now, it’s time for dinner. A favorite stop of ours is Sloppy Joe’s. I know, I know, it can be a bit touristy, but I still love this place. The food is always good, the drinks are poured strong and they offer live music. Who could ask for more?

Speaking of live music, plan a stop at the Smokin’ Tuna, one of the best places in Key West for music. They have an outdoor courtyard that offers shade and cold adult beverages.

Most of the time I suggest sunset celebration at Mallory Square, but this night, we opted for a different perspective. Sunset from the top of Schooner Wharf. This is the perfect place to see the harbor, enjoy a cold beverage and listen to live music.

Today, hubby heads off to enjoy a morning out on the water fishing. Me… well, I do what I love to do while in Key West, I head out for a morning walk. Who doesn’t love a morning walk around Key West? I love to look at the historic homes that are scattered all over this small island. It’s one of the great things about the Island, they have kept the charm and preserved its history.

Historic Walking Tour

When I get back, it’s time for breakfast. I head down this wandering path at Winslow’s and partake in their complimentary breakfast. It’s a basic continental breakfast. It’s served in the bar area. Enjoying my second (and maybe third) cup of coffee, I did a bit of work. Caught up on a few emails, and, worked on this blog post. At the bar, is a great spot to work. I don’t spend too much time working… after all, there is a lot more to see and do before Kevin returns from his fishing trip.

Kevin returned after a successful fishing trip, and we then set out for the next adventure. Kimpton Hotels hosted us for a tour of their Lighthouse property. This place is very cool Across the street from the Hemingway House, it offers a great view of the lighthouse and they have a very nice bar.

Not staying at the Lighthouse? No worries, the bar is open to the public, Plan to stop in and enjoy this place. The bartender is engaging and can mix many amazing cocktails. We had the best time trying the house specialties. We actually couldn’t decide which ones we liked best. It’s ok to like them all, right?

While in Key West, it seems to always be cocktail time. With that in mind, we had time before our dinner reservations and headed over to General Horseplay. This place is known for their cocktails and fun Happy Hour. It’s a great place to start off an evening.

For dinner… we were hosted by Poke in the Rear. Don’t overlook this place. It was, one of the best dinners we had while on Island.

Today we have a quick bite of breakfast and then head out to explore the streets of Key West. Being married to a photographer, I spend a lot of time wandering around. But, I wouldn’t have it any other way. We saw roosters, flowers, palm trees, and stickers. All my favorites.

Grabbed a cold brew from Cuban Coffee Queen and walked around the Historic Seaport.

Heard the band starting to play at Sunset Pier… which means we are stopping to listen and enjoy a cold beverage. Here’s where I would insert the idea of having free time built into your Key West itinerary. If you “had” to be somewhere … you might miss out on an awesome view, cold beverages, and amazing live music.

A few more stops for pictures and then we are heading back to Winslow’s Bungalows. Not only do they have a great pool bar and pool area, but they offered a free tasting of Mutiny rum. It was yummy and the story was just as interesting.

We didn’t have any dinner plans to speak of so we “thought” we would head over to Mallory Square and enjoy sunset and then play it by ear. I think that’s a great way to spend any evening in Key West, at least one night. No particular plans and let the evening unfold.

Well, as we walked by Little Pearl and saw they had two chairs open at the bar… and we hopped on the chance to eat at Little Pearl. This place offers a tasting style menu and is worth every penny if you can get a reservation.

We have a later flight, also planned on purpose, which gives us almost a full day to play in Key West. What is always fun to see is the “guest” ships that dock at Mallory Square. On this day we were able to see the USCGC Eagle. This 295-foot, three-masted barque is used as a training vessel for future officers of the United States Coast Guard. This is also known as “America’s Tall Ship” and is the largest tall ship flying the Stars and Stripes and the only active square-rigger in US service. Very, very cool to see in Key West.

Then it was off to lunch at First Flight. This is the Southernmost microbrewery and they offer a great courtyard seating area and a wonderful menu.

Afterward, we head off to the airport to head home. As per usual, we grab a last vacation cocktail and share a frozen Key Lime pie on a stick (dipped in chocolate).

We tried new places for food and drinks and had plenty of down time to relax. That’s what makes the perfect vacation… a perfect balance.

More…

I get it, we didn’t do much on this trip. But, we had a really good time. If this seems a bit too slow for you, then check out these ideas:

• Take a guided tour – a food tour, a walking tour, a ghost tour ( see our recommendations here )
• Take the ferry (or seaplane ) out to the Dry Tortugas National Park – be sure to book this one in advance as it sells out quickly.
• Head out on the water to snorkel the coral reefs
• Go up the Keys for a day trip and see Bahia Honda State Park, sea turtles, or the Key Deer on Big Pine Key.
• 3 Reasons Smathers Beach is the best
• Visit one of the 18 museums on the island… like the Truman Little White House

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Ultimate Weekend Itinerary for Key West

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Looking for the perfect weekend getaway.

Look no further than Key West!

This sunny destination is perfect for relaxation, exploring and fun in the sun. Check out our ultimate weekend itinerary to make the most of your time in paradise.

Getting Around During Your Key West Weekend Trip

Planning a weekend trip to Key West? Get ready for three days of rest and relaxation in the sunshine! Whether you prefer to take things slow and stroll along Duval Street or rent a bike, scooter or electric car to explore all the nooks and crannies, you will have plenty of opportunities to get around during your Key West weekend trip. And, when you get tired of walking, the Conch Tour Train can give you a guided tour of the best places to visit and hang out in Key West.

Explore Classic Key West

If you’re planning a trip to Key West, why not explore the classic sights? From taking a stroll on the gorgeous beaches with their crystal-clear waters and powdery white sand to soaking in the key’s rich history at the Ernest Hemingway Home and Museum, there’s something for everyone to discover. Make sure to appreciate the key’s unique culture, as it continues to remain a beloved destination for so many. Here’s some of our favorite classic Key West attractions worth exploring on day one!

Southernmost Point Concrete Buoy

Planning your Key West itinerary? Don’t forget the iconic Southernmost Point concrete buoy, a must-see destination found at the end of Whitehead Street in Key West, Florida. Marking the southernmost point of the mainland United States, it’s a great place to take photos and to say you’ve seen where the USA ends. Get there early too — while it is open 24/7, crowds form in the mornings and afternoons to get their turn at taking pictures. So, head over to catch a glimpse of this landmark before tackling those sunsets on Key West’s beautiful beaches!

Hemingway Home and Museum

The Hemingway Home and Museum is a must-see for Hemingway fans. Located in Key West, FL, the Hemingway Home and Museum provides an intimate and detailed look into Hemingway’s life and work — from his family artifacts to his Nobel Prize and Pulitzer awards. In addition to Hemingway’s personal belongings, the museum offers educational programming that highlights Hemingway’s works as well as tours of Hemingway’s home with a guide that tells stories about Hemingway’s writing process. It truly is a unique experience for Hemingway fans of all ages and backgrounds!

Brunch at Blue Heaven

Brunching at Blue Heaven in Key West is an experience like no other. From the moment you walk through their doors and take in the unique atmosphere of this lively restaurant, it feels like stepping into a special place. The menu is extraordinary — fresh seafood, local favorites and delectable morning options are all on offer. Each dish is lovingly prepared with the highest quality ingredients and an inspiring array of spices and flavors. Brunch at Blue Heaven will leave you feeling satisfied and eager to return!

Key West Lighthouse

The Key West Lighthouse is the perfect landmark to visit if you’re looking for a Key West getaway. Located on historical grounds with breathtaking views, it is sure to provide an unforgettable experience. The grounds are home to many colorful birds, making it a great place to go for some bird-watching as well. Not only can you take a tour of the grounds but visitors can learn all about local history, cultural artifacts and nautical items. Whether you’re looking for an educational outing or just want to soak up the amazing views and atmosphere, this old lighthouse will surely not disappoint!

Check Out Duval Street

If you’re looking for a one-of-a-kind experience, look no further than Duval Street in Key West. Boasting an incredibly unique atmosphere and entertainment options, this exciting street is the heart of Key West. Check out the shops, restaurants and bars that line the street — Duval offers something for everyone. With endless nightlife, diverse cultures and rich history all converging on one vibrant street, it’s no wonder that Duval Street has developed such a devoted following over the years.

Time to Enjoy the Ocean!

Day two of your Key West itinerary is no less exciting than the first day! Spend the morning soaking up some sun at Higgs Beach and then enjoy a traditional Cuban coffee to get your day started. Head over to the Key West Butterfly and Nature Conservatory to explore their exotic butterfly gardens. In the afternoon, take an incredible Sunset Sail around Key West’s harbor to truly appreciate the beauty of Key West. Then, end your day with a visit to Schooner Wharf Bar for live music and drinks with friends! With so much to do, you won’t want to miss this Key West itinerary’s day two!

Sunrise at Higgs Beach

Sunrise at Higgs Beach is an unforgettable experience that you won’t want to miss! Taking in the sight of the sun rising over the horizon while standing on a peaceful beach is something everyone must do at least once. So, make sure to plan your trip so you don’t miss out! Sunrise at Higgs Beach is best enjoyed during the early morning hours when the sun is just beginning to peek out from its sleep. Sunrise is also a great time for other activities, such as paddleboarding or kayaking, so make sure to take advantage of this unique experience.

Drink Cuban Coffee

Make sure to also enjoy a cup of Cuban coffee at Cuban Coffee Queen’s Waterfront location. Taking a break and sipping on some authentic Cuban coffee is just what you need after exploring the best of Key West. Take a walk and stroll down the pier with your cup of café cubano for an experience unlike any other! Cuban coffee is best enjoyed during the afternoon hours when you can truly enjoy the ambiance of the Key West waterfront.

Key West Butterfly and Nature Conservatory

Don’t forget to make some time to visit the Key West Butterfly and Nature Conservatory. This unique conservatory is home to some of the rarest and most beautiful butterflies in all of Florida. You can take a self-guided tour of the conservatory and learn about all the different species of butterflies found there. There’s also a gift shop where you can purchase souvenirs to take home with you. No matter what time of year it is, visiting the Key West Butterfly and Nature Conservatory will be an unforgettable experience that your family and friends won’t soon forget.

Sunset Sail

A sunset sail is a wonderful way to end your day, so make sure to take advantage of this incredible opportunity. Enjoy the view of the sun setting over the horizon while sailing through the waters of Key West — it’s something you won’t soon forget! A sunset sail is best enjoyed with friends and family, so grab your hats and get ready for a memorable voyage. You’ll be talking about it for years to come.

Schooner Wharf Bar

Schooner Wharf Bar is the perfect place to go for a late-night snack or drink after a long day of sightseeing in Key West. With an incredible selection of tasty rum-based drinks and delicious snacks, Schooner Wharf Bar is the perfect way to end your day right! Take your time exploring Schooner Wharf Bar, and make sure to sample a few of their signature cocktails. Schooner Wharf Bar is a unique experience that you won’t soon forget and will be one of your most memorable nights in Key West! So, don’t forget to add Schooner Wharf Bar to your list of must-visit spots while visiting Key West — you won’t regret it!

Best Things to Do in Key West

Day three of your weekend in Key West is all about having a laid-back day of relaxation. Start the day off right with a mouthwatering boozy brunch at Glazed Donuts. After you’ve refueled, it’s time to take full advantage of all that Key West has to offer! Whether you decide to snorkel the colorful coral reef, grab some delicious food to-go or shop for handmade leather sandals at Mallory Square, you won’t be disappointed. If you’re looking to explore a bit more of the island’s history, head over to Fort Zachary Taylor State Park or the Truman Little White House. Last, but not least, make sure to get the famous Kermit’s Key Lime Pie before your weekend comes to a close.

Breakfast at Glazed Donuts

Whether you’re looking for a relaxing weekend escape or an adventurous day of sightseeing, Key West has something to offer everyone! Get the most out of your time here by beginning your day with breakfast at Glazed Donuts. Enjoy the unique flavors of this sweet and savory island paradise!

Fort Zachary Taylor State Park

Located in Key West, Fort Zachary Taylor State Park is a popular spot for visitors and locals alike. The park offers stunning views of the Gulf of Mexico, as well as plenty of opportunities to explore its historic fortification. Visitors can take a guided tour of Fort Taylor or wander around on their own to explore the old cannons and armory. The park also features a beach, picnic areas and nature trails, making it the perfect spot to spend an afternoon. Fort Zachary Taylor State Park is a great way to get away from it all and experience some of Florida’s history.

Truman Little White House

The Truman Little White House in Key West, Florida, is a historic museum. Built in 1890 by railroad tycoon William Curry, it served as the winter retreat of President Harry Truman from 1946 to 1952. Truman held many meetings here with dignitaries such as Winston Churchill and made key decisions about U.S. foreign policy during his stay. Today, the Truman Little White House is a popular tourist attraction with educational tours and programs that allow visitors to learn about Truman’s presidency and the history of Key West. Visitors can also explore Truman’s original furnishings, artifacts from his time in office and photographs from his years here.

Kermit’s Key Lime Pie

Kermit’s Key Lime Pie is a beloved Florida classic. It’s tart and creamy — the perfect combination of sweet and tangy. Baked fresh every day with luscious Key limes from South Florida, this pie is sure to be a hit with your family and friends. The graham cracker crust adds just the right amount of crunch to make this pie irresistible. Whether you’re enjoying it alone or sharing it with someone special, Kermit’s Key Lime Pie is sure to be a hit!

Mallory Square

Mallory Square in Key West is the place to be during sunset. It’s where locals and visitors alike congregate to watch the sun sink into the horizon and admire this picturesque part of Florida. The City of Key West has designated Mallory Square as the official location of the Sunset Celebration, featuring local street performers, musicians and craftsmen who display their work for all to enjoy. Whether you’re looking for live music, stunning sunsets or just want to people-watch, Mallory Square is the spot to be. The atmosphere is one of community and celebration that can only be experienced in person.

Dinner at Latitudes

If you’re looking for a delicious dinner spot, Latitudes is the place to go. Located in the heart of town, this chic restaurant offers an eclectic menu featuring both traditional and modern dishes that will please everyone in your party. The atmosphere at Latitudes is warm and inviting with its wood furnishings, cozy lighting and lush greenery. As you dine, enjoy the serene music that plays in the background — it creates a soothing ambiance perfect for an intimate dinner with friends or family.

When you’re ready to order, choose from Latitudes’ ever-changing menu of locally sourced dishes. Delicious appetizers, such as crispy calamari and beef carpaccio, will get you started. Then, pick your favorite entrée, such as the steak frites or roasted salmon, to complete your meal. And, don’t forget to save room for a sweet dessert!

Key West Travel Tips

Know Before You Go

Exploring Key West is a fun and exciting adventure. Whether you’re planning on a quick weekend getaway or an extended stay, here are some Key West travel tips to help ensure your trip goes smoothly.

Getting Around

Key West is a small island city with limited public transportation options, so plan on renting a vehicle or using ride-sharing services to get around. Key West also has a few bike-share programs and electric scooter rental companies, so depending on your budget and mobility needs, you’ll have no trouble getting where you need to go.

Key West is located in the subtropics, so expect hot and humid weather year-round. The temperature usually ranges from the high 70s (Fahrenheit) in winter to the low 90s in summer, but expect it to feel much warmer due to the humidity. Make sure you pack plenty of sunscreen, a hat and light clothing for your Key West getaways!

Where to Stay

Key West is a great destination for both budget travelers and luxury seekers. The island offers plenty of hotels, Airbnb rentals, and camping sites for all kinds of budgets. For those looking for more luxurious options, Key West also has several resorts and boutique hotels that offer top-notch amenities, such as spas, pools and private beaches.

No matter where you stay, chances are you’ll be able to find a hotel or rental near Key West’s attractions, restaurants and nightlife. So, whether you’re looking for budget-friendly accommodations or something more upscale, Key West has the perfect place for your getaway!

Best time to Visit

If you’re planning to visit Key West, you’ll want to make sure you have the best time possible. To do this, you should be aware of the best time to go. Generally, the best time is between March and May or October and mid-December. The temperatures during these months are mild and pleasant, typically in the mid-70s to low 80s. The lower humidity makes for a great time to explore all that Key West has to offer — from Mallory Square and Kermit’s Key Lime Pie to the Truman Little White House and Fort Zachary Taylor State Park. Be sure you have your camera packed, so you can capture the best of your experiences — from the sunrise at Higgs Beach to the Key West Lighthouse. And, don’t forget something sweet for breakfast at Glazed Donuts or a trip to the Butterfly Conservatory!

Is two days enough in Key West?

If you want to relax, two days could be enough. However, you need a few more days to explore the island, as there are various things to do in Key West. There are many unique attractions, such as the Ernest Hemingway Home and Museum and Mallory Square’s nightly Sunset Celebration. You can also visit various restaurants, bars and shopping centers. Having a Key West itinerary can be helpful.

How many days do you need to visit Key West?

You should plan for at least four days and have an ultimate weekend itinerary. Spend one day lounging on the beach, another day taking a boat tour and the rest of your time wandering around the city. Visit local boutiques, eat delicious food from the seafood markets and explore the natural beauty of the area.

How to spend half a day in Key West

You can start off your day with a coffee and a stroll through Duval Street. Check out the various shops, restaurants and eclectic architecture of the buildings. Don’t forget to take in the street performers, who often bring laughter and entertainment to the area. Consult with a seasoned Key West trip planner to get the best plan.

When is the best time of year to visit Key West?

The best time to visit Key West is between late spring and early fall. The temperature is warm, the days are long and sunny and the beaches are open. The island offers various outdoor activities, including snorkeling, sunset cruises, swimming and kayaking.

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• Florida Keys

The Best Weekend Itinerary for Key West

See recent posts by Neil Gladstone

Ernest Hemingway may be Key West’s most well-known former resident, but plenty of famous faces have sailed, drank, and partied their way through the popular Florida island getaway. Jimmy Buffet, Judy Blume, and Ralph Lauren have all spent time basking in the mix of adventurous artsiness and beachside pleasures here. The island is approximately four square miles, so it’s small enough to tackle on a quick weekend jaunt, especially for those looking for a break from the cold winter up north. With that in mind, we rounded up the best itinerary for a weekend in Key West.

Hotels in this story

Friday: Arrive and Check-In

Sunset Key Cottages, Key West/Oyster

While Miami may be the most popular airport destination for a trip to Key West, keep in mind you’ll need to drive over three hours after you land. If you can afford to fly directly into Key West (the extra mileage will likely add $50 or more to your ticket), you may save yourself some road wear and gas money. 

Once in town, check into your hotel. The island offers many properties with white-sand views and ultra-plush rooms. The Casa Marina Resort (part of the Waldorf Astoria chain) features in-room espresso machines and a swimmable beach. The Sunset Key Cottages caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities, including a lovely pool, a gorgeous (though somewhat rocky) beach with palm trees and clear, calm waters, and a pleasant spa. However, note that it’s set on a small residential island off Key West and only accessible by boat.

Stroll Through the Seaport

Ocean Key Resort, Key West/Oyster

Key West’s historic seaport is a great introduction to the destination since it has a lot of what visitors want to see plus access to stellar sunsets. Several local watering holes start happy hour at 4 p.m., so hopefully you’re prepared to get your drink on. Hungry travelers who want to get started on a Key West seafood binge should head over to the Half Shell Raw Bar, which shucks 200 oysters, on average, every happy hour. For anyone inspired to have a cookout on the beach, Half Shell also owns its own fish market. Conch Republic Seafood Company offers 80 brands of rum and claims to have the largest bar between Miami and Cuba. Regardless of what you’re drinking, the restaurant’s four, 160-gallon saltwater tanks filled with local marine life make for some seriously impressive decor.

You can also scope out one of the numerous fishing day trips that leave from the port. Clearly Unique Charters rents glass-bottom kayaks and the Key West Eco Tours meanders through coral gardens. Sailers can also choose to take a trip on the svelte Echo Catamaran or historic, 90-year-old Hindu wooden schooner.

Celebrate the Sunset

Key West/Oyster

Commemorate the end of a fun day with drinks along the water. Grab a pastel stool on Sunset Pier (located at Ocean Key Resort) and soak in a horizon filled with tangerine and lavender hues. Another popular watching spot is the Galleon Tiki Bar at the Galleon Resort and Marina. Plenty of nearby bars have excellent happy hour specials, so as long as you can see the sunset, be sure to celebrate. After a long day of travel you’ll probably want to rest up for the big day ahead.

Saturday: Get a Cuban Breakfast

Cayobo/Flickr

Since Cuba is only 90 miles away, go ahead and salute our southern neighbors with a pressed breakfast sandwich. Cuban Coffee Queen (also located near the seaport) serves the Key Wester (eggs, American cheese, and chorizo) for $7 and a Cuban breakfast burrito (eggs, cheese, rice, and beans) for $8.50. Many tourists say the best local food is also the cheapest — find out for yourself, then wash it down with the Queen’s roasted java.

steve lyon/Flickr

If you’ve planned ahead, you can board one of the numerous charter trips from the seaport. Much of the game fishing is — by law — catch and release. However, grouper, mahi-mahi, and snapper can be eaten. Many of the expeditions include fishing gear, or you can rent it at places such as The Angling Company or Key West Bait & Tackle. Those who don’t have a hankering to hook a fish can choose from sailing trips that include dolphin watching and snorkeling. Luxury excursions serve up the sunset with Champagne. Some boats even take tourists out to Dry Tortugas National Park, home to one of America’s largest coastal forts. If you can fit in a trip to Dry Tortugas during the weekend, it will likely be worth the extra organizing.

Stroll Duval Street

Duval Street, Key West/Oyster

Depending on your perspective, Key West’s Duval Street is party central and top-notch people-watching territory or an extremely long tourist trap. If you’re in Key West, you definitely need to stop by and see the array of crafty boutiques, brash bars, and mom-and-pop fresh seafood restaurants. Taking a stroll is a nice way to unwind from a half-day boat ride. While there are plenty of tourists who go on a “Duval Crawl,” the street is also safe and family-friendly. You can easily browse the shop windows and get a slice of Key lime pie or a couple of scoops of ice cream. The clothing store options can be either kitschy or artisanal.Indigo boutique has bohemian-inspired swimsuits and handmade jewelry. The Green Pineapple sells affordable  eco-chic choices, including Rich Hippie fragrances and animal print home decor. For eats, DJ’s Clam Shack has one of the best lobster rolls in town ($18) and Mangoes is known for its friendly service and Caribbean-influenced comfort food.

Go on a Self-Guided Art Tour

Mark Mitchell/Flickr

Key West’s art galleries boast a collection much more impressive than you would expect to see on an island at the tail end of Florida. Many of these outposts are located on the streets just beyond Duval, making for an easy detour during a shopping tour. Gallery on Greene showcases the work of several Pulitzer Prize-winning photographers and cartoonists as well as Cuban and Key West painters. Curator Nance Frank has worked with museums in Switzerland, Chile, New York, and Cuba, and developed a collection that also includes pieces by one-time local residents Tennessee Williams and Annie Dillard. Frank also takes groups to Cuba for private art tours. Alan Maltz, the official wildlife and fine art photographer for Florida, keeps his fine art pieces in an eponymous gallery. In addition to nature prints, he also sells images of the Everglades and coastline on note cards and lithographs. The Key West Art Center celebrates local artists who work in numerous disciplines and also organizes the Key West Craft Show in January and Old Island Days Art Festival in February. If you want to view some of Key West’s best art, be sure to keep an eye on the clock, as many of the galleries close at 5 or 6 p.m. Tip: You may want to call ahead to check on closing time.

Enjoy a Night Out on the Town

If you’re only in Key West for the weekend, Saturday is your big night to go out, and there are plenty of bars to enjoy. Sloppy Joe’s opened its doors on the day alcohol prohibition ended — December 5, 1933 — and has been grooving ever since. Yes, Ernest Hemingway drank there and the bar is now home to an annual look-alike contest every July during the Hemingway Days festival. It also has live bands — blues, country, rock — every night. The Bull and Whistle Bar has three floors that each have a different theme, including the Garden of Eden — a rooftop watering hole that’s clothing optional. Feeling a little more introverted? The Green Parrot Bar is a dive located a block off the main drag, and is popular with locals and tourists looking for a low-key place to tie one on and listen to classic soul and rock on the jukebox. If you’ve planned wisely, your hotel is within walking (or stumbling) distance.

Sunday: Have Breakfast in Heaven

Sam Howzit/Flickr

If you want a memorable morning, Blue Heaven has al fresco dining under the trees and a selection of silly artwork. The Blue Heaven Benedict gives the traditional dish a local twist with lime hollandaise sauce. The lobster and grits are a hearty mix of upscale and down-home.

Soak in the Key West Culture

Mandy/Flickr

After a night of debauchery, pop your synapses back into action with a little Key West culture. First stop: The Ernest Hemingway Home, an 1851 Spanish Colonial-style structure where the writer finished “A Farewell to Arms” and “To Have and Have Not” and lived with his wife Pauline. The Hemingways’ European art collection still decorates the house. Feline fans will appreciate the six-toed cats that roam the grounds — descendants of the one that lived with the Hemingway family. 

The San Carlos Institute was the location where Jose Marti launched the expatriate movement to free Cuba from Spanish colonial rule. Cuba’s government still owns the stately house with scrolled details and ornate ironwork. 

In the early 1900s, the Key West fishing industry nearly drove turtles to extinction. The Key West Turtle Museum explains how the species was brought back from the brink and also hosts lectures about other local conservation efforts. 

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Ultimate 3 Days in Key West Itinerary for Beach Lovers

Key West, Florida is one of the most popular destinations in the USA.

With its beautiful beaches, charming old town area, and amazing tropical weather year round, many visitors have this southern Florida vacation on their bucket list! 

Key West is rich in history and culture, with a diverse population that makes it an exciting place to visit.

Key West has plenty of attractions such as Ernest Hemingway’s Home & Museum, Duval Street with its eclectic stores, clubs, and restaurants, Historic Key West Seaport, southernmost point, the Key West lighthouse, and its beaches. 

Our Key West itinerary takes you around the many amazing attractions the city has to offer. 

Tourists can also enjoy many water attractions such as snorkeling, scuba diving, whale watching, dolphin watching, deep sea fishing, kayaking and guided tours by boat or airboat!

Dotted Globe contains affiliate links. If you click one of them, we may receive a small commission at no extra cost to you. Read my full  Disclosure  here. Thank you!

Weekend in Key West Itinerary

Explore Key West in a weekend or 3 days by following our perfect Key West itinerary.

Enjoy the attractions and activities including pretty beaches, historic sites, and amazing restaurants.

If you find yourself in Key West for a weekend trip, here is what you should do to make the most of your visit:

Day 1: Old Town Key West

Start your day by exploring Old Town Key West and its historic buildings.

Next stop, Southernmost Point in Key West and eat some famous key lime pie.

End your day at Duval Street and Mallory Square.

Old Town Key West

There are lots of things to do and see in Old Town, making it a popular first stop on the Key West Weekend itinerary.

You can walk to see the historic buildings on a self guided tour and see attractions such as Railroad Depot and East Martello Fort.

You can also take the hop on hop off Old Town trolley tours which stop at all popular attractions.

See the hens walking down the streets, browse shops such as the Conch Shop, and stop at Sloppy Joe’s for some drinks.

Key West Southernmost Point Buoy

Key West’s Southernmost Point Buoy is a popular spot to visit in Key West.

This is the southernmost point in the continental United States.

The buoy is an iconic symbol for visitors to see while they are exploring Key West Southernmost Park and Pier.

Try some Key Lime Pie

One of the most popular things to do in Key West is to enjoy some delicious key lime pie!  

This sweet & tart dessert tastes especially refreshing when you’re spending your day soaking up the sun while exploring this island paradise. 

Key Lime Pie has been a staple in Key West for over 100 years and there are several restaurants famous for the delicacy.

Some of the best restaurants to try key lime pie include Ricky T’s, Florida Keys Café, Key Lime Pie Company, and Conch Republic Grille.

Definitely add this to your bucket list, while spending 2 days in Key West.

Sunset Celebration at Mallory Square

One of the most well-known events in Key West is the daily Sunset Celebration at Mallory Square.

Mallory Square is the heart of Key West. It is located right on the water and has an unobstructed view of the ocean! 

Locals and tourists alike come here to enjoy stunning sunsets, live music, street performers, food stands, and souvenir shopping. 

Watching the day end with a brilliant display of colors in the sky over the Gulf of Mexico at Mallory Square is an unforgettable experience.

The Mallory Square sunset celebration draws large crowds daily. We recommend arriving early for the best views.

Duval Street Shopping & NightLife

Buy amazing souvenirs for yourself and loved ones on Duval Street in Key West.

If you’re more interested in going out at night than buying key west souvenirs, then Duval Street also has an excellent nightlife scene with karaoke, DJs and live bands!

You can go bar hopping and paint the town red on your Key West trip.

Sleep and wake up early to finish your Key West itinerary 2 days.

Day 2: Museums and beaches

See your favorite museums before leaving Key West.

We recommend the Ernest Hemingway Home and Museum or Harry Truman White house.

If you have small kids, consider visiting the Key West aquarium.

Relax on the beaches near Fort Zachary Taylor and have a picnic on the sand – a must activity on the Key West itinerary 3 days.

End the day at the Historic Seaport admiring the docked boats and enjoying fresh seafood.

Harry S Truman Little White House

The Truman Little White House is a historic house museum in Key West, Florida. It was the winter White House for President Harry S. Truman. 

The property includes a beautiful Victorian cottage) and grounds that offer spectacular views of Old Town Key West. 

On guided historic tours of the property, visitors can see several artifacts including paintings by Norman Rockwell; period furniture such as writing desk used by Franklin Roosevelt and sofas given to Truman by Queen Elizabeth; books about Truman, as well as his personal items.

The Truman Little White House is a must for history lovers!

Ernest Hemingway Home Museum

Key West’s top attraction for literary lovers!

The Ernest Hemingway Home and Museum is a house museum in Key West, Florida.

The house has been carefully restored with original furnishings and offers historic tours to visitors.

Visitors can see his writing desk, first editions of Ernest Hemingway books on the walls as well as other personal items he used during his time there. 

The house is a U.S. National Historic Landmark and popular for its architecture, gardens, six toed cats, and proximity to Duval Street.

Key West Aquarium

The Key West aquarium has a collection of more than 40,000 aquatic plants and animals for visitors to explore.

It’s a great resource for Key West visitors who want to learn about the incredible creatures that live in the waters of southern Florida.

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park is one of the most popular tourist destinations for those visiting Key West. 

Located on the coast, it offers a spectacular view of both the Atlantic Ocean and Gulf of Mexico. 

This historic fort was built to defend Key West from pirates and foreign invaders. Today, it is home to a museum with exhibits on the history of Key West. 

Visitors can also enjoy biking or hiking along the trails around the park. The park also has picnic tables with sweeping views of the ocean. 

Key West Lighthouse

There are many reasons why the Key West Lighthouse is a tourist destination. 

It’s situated on Fort Zachary Taylor and has been restored to its original condition.

On a tour, visitors can also explore the lighthouse and its grounds to see attractions such as an old cistern with a conch shell motif, cannons that date back to the 19th century, and beautiful views of Old Town Key West and the Atlantic Ocean. 

The best time to visit this historical landmark is at sunset.

For many, the light is the highpoint of the weekend in Key West, Florida.

Key West Butterfly and Nature Conservancy

This beautiful conservancy is a must-see attraction in Key West – definitely visit it if you have the time on your Key West 2 day itinerary.

The Key West Butterfly and Nature conservatory features live exhibits with nearly two hundred species of native insects including many endangered or threatened species or butterflies.

The nature conservatory has lush tropical gardens that are beautiful to take a stroll and offers amazing views of the coastline.

Key West Historic Seaport

The Historic Seaport is a place that exhibits the unique history and architecture of Key West’s past.

You will find museums, historic buildings, ships in docks, buskers dressed as pirates, and people strolling on the boardwalk.

The historic Seaport also has many bars and restaurants and is the perfect place to eat fresh seafood including raw oysters and conch fritters or to gulp down an oyster shooter!

After enjoying two days in Key West, head back with awesome tropical memories in your head!

Day 3 in Key West

For those visiting Key West and looking for ways to extend your trip or explore this part of Florida, here are some day trips that can be done from this southern Florida city.

Dry Tortugas National Park

The Dry Tortugas National Park is a remote, uninhabited group of islands and reefs well-known for its rich natural beauty. 

It consists of seven small islands (only six are open to visitors) and the surrounding marine area near Key West. 

The national park is located at the end of the Florida Keys, 90 miles west of Key West.

Dry Tortugas National Park is accessible only via ferry boat – the Yankee Freedom III – or by sea plane tour – both which depart from Key West.

The park is often visited on a day trip by tourists who want to experience the unspoiled nature in an untouched environment. 

The park’s main attraction is Fort Jefferson which was never completed but remains one of America’s most massive brick structures. 

Visitors can explore the island on foot or by boat, camp out under the stars, see the massive Fort Jefferson, or take advantage of one of many water activities available such as fishing, snorkeling and kayaking. 

Dry Tortugas has no lodging or campground facilities so visitors must bring their own food and water with them. 

Read More: Visit Dry Tortugas National Park day trip via Yankee Freedom ferry from Key West

Bahia Honda State Park

There are several state parks in the Florida Keys, but the most popular one is Bahia Honda.

It’s about an hour north of Key West and includes a nature trail that will lead to one of the most beautiful beaches in Florida.

The road here goes over the Seven Mile Bridge and offers panoramic views of the islands.

Florida Keys Road Trip

Key West makes the perfect base for exploring the small islands of the Florida Keys, including Key Largo.

The Florida Keys have a unique culture and way of life. They are an island chain that is known for their laid-back attitude, beautiful beaches, coral reefs, and warm weather. 

The Florida Keys also have some of the best fishing in the world! 

The water here is home to many unique species such as manatees, iguanas, and sea turtles, making snorkeling and scuba diving popular activities. 

You can extend your road trip on the popular Overseas Highway or US-1 all the way to Miami.

Apart from the Overseas Highway road trip, you can also enjoy other attractions such as Dolphin Research Center and state of the art Turtle Hospital on Marathon Key, John Pennekamp Coral Reef State Park, Florida’s first undersea park, which is home to a living coral reef, and the Islamorada artist community.

Read: Road trip Miami Florida Keys Itinerary

There are many other attractions near Key West such as the exclusive Sunset Key, Key Largo, and the Everglades!

Spend a day on the water

One of the most popular tours in Key West is kayaking to see marine life like manatees, Roseate Spoonbills, and dolphins.

Water Sports is also popular in Key West.

You can rent watercrafts like jet skis, fishing charters, and sailboats. Or enjoy parasailing to see the island city from above!

Romantic champagne sunset sail charter is popular with couples.

Dolphin cruises are preferred by families as are scuba diving and snorkeling excursions.

There are many dive shops around Key West that will take you on trips to see Key West shipwreck, treasures, and coral reefs.

You can create your own Key West sailing itinerary to explore the surrounding waters and reefs.

Key West 1 Day Itinerary

If you have less time, then use our one day itinerary for Key West.

Start your trip at the Southernmost Point Buoy and Mile Marker 0.

Then explore Old Town Key West and see historic buildings such as the Truman White House and Ernest Hemingway home.

Eat fresh seafood and key lime pie for lunch.

Spend a relaxing afternoon on the beach at Fort Zachary Taylor State Park.

End the day with watching the sunset in Mallory Square, followed by dinner on the Seaport.

If you love partying, enjoy the nightlife on Duval Street to wrap up your one day in Key West itinerary on a high note. 

5 Days in Key West

If you have more time, you can also plan a Key West itinerary for 5 days. 

Spend 2 days in Key West exploring the Old Town, museums, and beaches.

Then take a day trip to Dry Tortugas National Park and admire Historic Fort Jefferson.

Then rent a car and road trip the Florida Keys for 2 days.

Stop at attractions like Bahia Honda State Park, Islamorada, Marathon key, and Key Largo.

For Key West itinerary 4 days, skip the Dry Tortugas or spend just one day exploring the rest of the Keys.

Or if you like slow travel, spend all 4 days in Key West: 2 for the major attractions, 1 day on the water, and 1 day shopping and relaxing on the beach!

This relaxing alternative also works perfectly as a Key West honeymoon itinerary – you can enjoy quality time with your loved one in the charming city.

Or plan a Miami and Key West 4 day itinerary: spend 2 days each in both the cities!

You can also plan a Key West itinerary 7 days by driving all the way to Miami and spending time on South Beach, Ocean Drive, Wynwood Walls, and Little Havana.

Where to eat in Key West

There are many great restaurants, cafes, and seafood shacks serving delicious food in Key West.

Some of our favorites include Hogfish Bar & Grill, the Conch Republic Seafood Company, Blue Heaven, and Southernmost Beach Cafe.

Located in the heart of Key West, Blue Heaven Cafe serves amazing Caribbean food. This is  a local favorite and Key West institution.

Blue Heaven Cafe is great for breakfast to dinner and has live music too!

Must eats in Key West include fresh seafood such as conch fritters, fried oysters, Cuban sandwich, fish tacos, fresh fruit juices, and the iconic key lime pie!

Best Time to Visit Key West

The Atlantic hurricane season runs from June 1 to November 30 each year. If you plan a trip during this time, be prepared for storms, rainy days, and unexpected delays.

One of the most well-known events in Key West Florida is the annual Fantasy Fest that takes place every October.

This is one of the busiest times in the city, especially Duval Street, and you will need advance reservations.

Winter is also the busy season: high crowds and expensive hotels!

Spring is a great time to Key West for warm weather and low crowds.

Summer in Key West can be hot and humid but you can spend all the time relaxing on the beach, making the most of your Key West vacation.

Essential travel tips to explore Key West

It is easy to get around Key West. You can get an inexpensive taxi or even rent a scooter or an electric bike to truly experience the beauty of this vibrant city!

The bikes are our favorites: the Key West vacation itinerary will have you covering a lot of ground, and it’s not worth getting stuck in traffic!

You can also sightsee Key West on the Conch Tour Train –  a train ride that takes you around major attractions!

If planning to get a rental car, then be prepared for busy streets and almost no free parking, especially in downtown Key West.

Remember: there’s no cell phone reception whatsoever on the Dry Tortugas!

Don’t forget to bring your camera to capture the beauty of Key West.

We hope you liked our Weekend in Key West Itinerary.

More Southern Florida Travel Guides

Here are additional resources to help you plan your 3 Days in Key West weekend trip:

20 Best Tours in Key West, Florida

Best things to do in Key West with kids

Best Museums in Key West, Florida

Dry Tortugas National Park Visitor Guide

Miami to Key West Drive: 25 Best Itinerary Stops

3 Days in Miami Itinerary

22 Most Romantic Things to do in Miami for Couples

Ultimate Florida Road Trip Itinerary

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California Family Travel

By Gwen Kleist · April 10, 2023

How to Spend a Weekend in Key West

Last updated on May 23rd, 2024 at 06:54 pm

Wondering what to do in Key West? 

Located at the southern tip of the Florida Keys, Key West is an island of tropical sunshine, amazing water activities, and a lively downtown known for its haunting history and world-famous sunsets. Three days is the perfect amount of time to hit all the highlights.

We visit Key West often, so I have put together this itinerary for a fun and family-friendly Key West getaway to help you plan an amazing trip.

Table of Contents

Things to Do in Key West

Though only four miles long, there are many fun things to do in Key West and lovely spots to do absolutely nothing.

A weekend in Key West is a great escape, with or without kids! You’ll feel like you’re visiting a Caribbean island without the hassle of leaving the continental United States.

How Many Days in Key West Do You Need?

Key West is worth a day trip, but the more time you have, the better! You could easily spend a week in Key West, but 3-4 days is optimal if you want to do it all and still have time to relax.

If you only have three days for a Key West weekend getaway, you’ll need to pack a lot into each day if you want to hit all the popular attractions. But it can absolutely be done!

Here’s a three days in Key West itinerary to help you get the most out of your stay.

Day One: Explore Key West Historic Sites

The Florida Keys have a rich history and there are many Key West historic sites to check out. Most of these attractions can be easily reached on foot from most Key West hotels in town.

You can also take the Key West Hop-On-Hop-Off Trolley Tour , which I highly recommend! More than a tour, the trolley is fully narrated with interesting facts, history and legendary stories of Key West, all while providing transportation around the city. You can explore Key West at your own pace without having to worry about transportation or parking. Visit more than 100 points of interest and attractions around Key West  and hop off anytime you want.

► Explore Key West at your own pace on this highly-rated Hop-On-Hop-Off Trolley Tour

Hemingway Home & Museum

Start your Key West weekend by visiting Ernest Hemingway’s home. It is one of the most iconic things to do in Key West.

Not going to lie – I wanted to visit this iconic place to see the famous six-toed cats just as much as to see where Ernest Hemingway lived and worked during his years on Key West.

Nestled in the heart of Old Town Key West, this unique property was home for more than ten years to one of America’s most honored and respected authors. It’s where Hemingway worked on many of his literary masterpieces. The house is now a museum dedicated to the writer. Beautiful gardens surround the house.

The Hemingway Home & Museum is also home to approximately 40-50 polydactyl (six-toed) cats. A ship’s captain gave Ernest Hemingway a white six-toed cat. Some of the cats lounging around the museum grounds are descendants of that original cat, named Snow White.

The cats are well cared for and obviously used to visitors, so don’t hesitate to reach down and give the kitties some love if they look willing.

The Hemingway Home and Museum is located at 907 Whitehead Street.

Key West Lighthouse

After a visit to the Hemingway Home, take a quick walk to the Key West Lighthouse & Keeper’s Quarters. I On our first visit to Key West, I was surprised to find it is not located right on the water!

The Key West Lighthouse was built in 1848 by the U.S. Navy, who recognized the need because of the many coral reefs and shallow waters around the island.

Today the Key West Lighthouse serves as a museum dedicated to the lighthouse keepers who lived and worked there over the years. You can climb the 88 steps to the top for a fantastic view of the city, and go into the adjoining Keeper’s Quarters to view photographs and belongings of the former lighthouse keepers.

They Key West Lighthouse & Keeper’s Quarters is located at 938 Whitehead Street.

Key West Aquarium

When you’re done at the Key West Lighthouse, head back up to the Mallory Square area and have lunch! Then you are ready for a fun afternoon.

First stop: the Key West Aquarium.

The Key West Aquarium is located right next to Mallory Square in the heart of town. Originally built as an open-air aquarium in the 1930s, it is one of the oldest aquariums in Florida. Home to a variety of native sea creatures, visitors can get a good view of sea turtles, tropical fish, sharks, and alligators.

This aquarium is fairly small, and only took us about an hour to see everything. Educational talks and feedings occur every 30 minutes.

Although we weren’t sure if he’d be too old, my son really enjoyed the aquarium. He especially liked being able to feed the stingrays and sharks. Younger kids will like the touch tanks and craft table.

Shipwreck Treasure Museum

If you are visiting town with kids, the Shipwreck Treasure Museum is a must on your Key West itinerary!

Across from the Key West Aquarium is the Shipwreck Treasure Museum. This fun and unique museum takes visitors back to the mid-1800s, the era of the wreckers. It’s an interactive museum where kids can learn about Key West’s maritime history.

The Shipwreck Treasure Museum combines actors, films, and the actual artifacts from the wrecked vessel Isaac Allerton, which sank in 1856 in the Florida Keys.

Kids will especially enjoy the interactive exhibits and being able to climb up the 65’ tall lookout tower.

Discover Haunted Key West

Enjoy dinner (and perhaps a few drinks at Sloppy Joe’s) then end Day One of your Key West weekend getaway by exploring the darker side of town with a nighttime ghost tour.

My son and I went on the Ghosts & Gravestones Tour , which is a combo trolley and walking tour. The trolley took us past the city’s most notoriously haunted sites, and then into two buildings – the East Martello Fort and the Shipwreck Treasure Museum – to experience some haunts first-hand. Tours are led by “Ghost Hosts.”

The Ghosts & Gravestones Tour was cool and just moderately scary enough for my 13-year old. For older teens and the truly daring, make sure you borrow an electromagnetic meter from the tour guide to detect the presence of ghosts.

Day Two: In, On and Near the Water

With its tropical warm waters and some of the most amazing coral reefs in Florida, Key West is prime for snorkeling, jet skiing, parasailing, and other ocean adventures. Teens love being active, and this is an ideal option for the whole family.

There are several tour companies that offer fishing and watersport excursions in Key West.

We did a combo sailing and snorkeling tour with Sebago Watersports . If you prefer more action, you can request their Power Adventure excursion, with snorkeling, jet skiing, parasailing, kayaking, and paddle boarding. All tours provide food and drinks, and their staff is very attentive and friendly.

Another great option is to plan a visit to  Dry Tortugas National Park , home to the magnificent 19th Century Fort Jefferson. Located about 70 miles from Key West, the cluster of seven small islands is only accessible by boat or seaplane.

The park is home to a wide range of tropical birds, marine life, coral reefs, and Fort Jefferson, which is surrounded by a moat and was formerly used as a prison during the Civil War. Guided tours are available.

When you return to shore, spend some time at Mallory Square. Facing the Gulf of Mexico, the waterfront plaza is a hub in Key West’s historic Old Town and world famous for its sunsets.

► Travel Insight If you are headed to Mallory Square for the sunset, get there early! The area gets very crowded.

This nightly “Sunset Celebration” is one of the most popular things to see and do in Key West. This tradition began in the 1960s, and the celebration still takes place every day.

If you are headed to Mallory Square for the sunset, get there early! Every evening before the sun begins to set, hundreds of tourists gather at Mallory Square to watch the sunset and to enjoy exhibits of arts and crafts, live music and street performers. The area fills up fast!

You can also enjoy a Key West sunset sail and view the gorgeous sunset from a boat off shore.

Day Three: Butterflies and Beaches

Start your final day in Key West at the Key West Butterfly and Nature Conservatory .

More than 60 species of butterflies and 20 exotic birds fly freely throughout the glass-enclosed, tropical habitat within the Conservatory. It’s also home to a wide spectrum of bright and beautiful flowers, plants and bushes for the butterflies to land on, putting visitors quite literally in the center of all the action.

The Key West Butterfly and Nature Conservatory is located at 1316 Duval Street.

Just down the street from the Conservatory is the Southernmost Point, arguably Key West’s most famous landmark. A massive, colorful concrete buoy marks the Southernmost Point of the USA, which is closer to Cuba (90 miles) than mainland Florida.

This is one of the most photographed spots in all of Key West. As such, it also tends to get crowded as people line up to wait their turn to get a photo. It is not unusual to see upwards of 100 people in line.

On our visit we got lucky (if you can call it luck) to hop off the trolley at the site just as a torrential rainfall started. Armed in our rain ponchos, we were the only ones crazy enough to be at the shore. So while we didn’t have to wait in line to get a picture, we did get more than a little wet!

Rain or shine, don’t miss your chance to get a photo at the Southern Most Point in the United States.

End your Key West weekend getaway with some beach time and perhaps a fruity cocktail or slice of key lime pie. It is the perfect way to cap off the perfect weekend in Key West!

Key West Walking Tours

Key West is a destination best explored on foot! Consider adding a walking tour to your Key West itinerary if you’d like to see the major sights while getting some exercise and enjoying the fresh ocean air.

Key Wests offers a myriad of great walking tours – everything from pub crawls to historic walking tours to ghost hunts. You can search for free self-guided walking tour ideas online, or click here for a list of the best walking tours in Key West .

Key West Hotels: Where to Stay for Your Key West Weekend

Trying to decide where to stay in Key West? Here are our suggestions based on experience and reviews.

We made the Best Western Hibiscus Inn home base for our most recent weekend in Key West, and I highly recommend this hotel if you are on a budget.

The Best Western is conveniently located just one block from the popular Duval Street – Key West’s main drag – and within easy walking distance to beaches, shops, restaurants, entertainment and Key West’s top attractions. It has large rooms, a fantastic pool, and offers free breakfast every morning (a big money-saver, especially when traveling with kids!)

► Read our full review of the Best Western Hibiscus Motel in Key West .

Alternatively, here are a few other hotel options closer to the water in Key West:

Opal Key Resort & Marina has what many consider the best location, right next to Mallory Square on the marina. It features beautiful grounds and a nice outdoor pool, and is just steps away from all the area’s shops, restaurants, attractions and museums.

Margaritaville Beach House Key West is in a quiet area just steps away from Smathers Beach.

For a more budget-friendly option, check out the Marriott Fairfield Inn & Suites Key West . Located just a pinch away from downtown Key West but still right on the water, Fairfield Inn offers a complimentary breakfast and nice outdoor area.

Getting to Key West

There are several options for traveling to Key West.

If you’re thinking of a road trip for your Key West weekend, the drive from Miami to Key West is 165 miles and will take just over three hours if you don’t stop.

But of course, you’ll want to stop along the way!

The Overseas Highway through the Florida Keys is one of the most scenic stretches of road in the country, with ocean vistas in every direction and lots of fantastic spots to stop along the way.

The other option is to fly directly to the island for your Key West weekend getaway! The Florida Keys are served by Key West International Airport and though the airport is small, it is served by many airlines with direct flights from a number of US cities.

Although the road trip is an adventure in itself, flying into Key West International Airport will allow for more time to explore the island. Key West is fairly small, so you won’t need to rent a car once you arrive unless you want to! Take a taxi or Uber to your hotel, and from there the town is walkable or you can hop on the trolley to get around.

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Vacations in Key West

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Most popular key west flight and hotel deals, search by stars, search by review score, search by board, search by price, search by freebies, when to book a vacation in key west, tips for finding key west package deals.

• There are loads of types of vacations in Key West and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $614; Family vacation $582; Romantic vacation $578; Luxury vacation $708.

Why should you book a vacation package to Key West?

There are many points of interest along Key West, including Ernest Hemingway's home, Dry Tortugas National Park, Martello Towers, and the Key West Aquarium. A rental car is the easiest way to travel at your leisure between these popular cultural attractions.

When should you book a vacation package to Key West?

The best time to visit is between March and May before the heat and crowds of summer tourists arrive. However some of the most popular cultural festivals include Ernest Hemingway Days, Goombay Festival, and Fantasy Fest, which take place in the summer and fall.

Where should you stay in Key West during your vacation?

For any vacation type in key west:.

Ocean Key Resort-A Noble House Resort lets you soak in the island's charm with a barside pool, private cabanas, and uninterrupted views of the Caribbean. Located on Key West's biggest island, it's easy to connect via rental car from Key West International Airport.

Hilton Garden Inn is part of the renowned collection of Keys hotels which features year-round outdoor pools, modern tropical décor, and friendly knowledgeable staff. Consider taking a lyft, uber, or taxi from Key West International Airport to avoid paying parking fees.

For family vacations in Key West:

The Marker Waterfront Resort is one of the newest hotel additions to Key West, providing updated amenities and an intuitive layout. Keyshuttles will transport the whole family from the airport to your hotel's front door from Key West, Fort Lauderdale, or Miami International Airport.

Southernmost Beach Resort on Duval Street is close to boutique shops, art galleries, eclectic restaurants, and non-stop nightlife. Daily bike rentals are also available from several locations to keep your family entertained and active on your Key West getaway.

For romantic vacations in Key West:

Chelsea House Hotel is a quiet historic inn with an acre of botanical gardens so you can travel back in time to the days when Ernest Hemingway called these islands home. The VIP concierge can help guide you towards your best transportation options on the island.

The Gardens Hotel offers intimate cottages with tropical verandahs for a romantic beach vacation in Key West. This hotel is located just 3.7 miles from EYW Airport.

For luxury vacations in Key West:

Crown Plaza Key West-LA Concha is a historical landmark situated on the popular Duval Street. It puts you within easy reach of Key West's most popular shopping district. Key West International Airport is just a few miles away and easily accessible by taxi.

Hyatt Centric Key West Resort and Spa offers sweeping views of the Caribbean, docks, Mallory Square, and the Key West Aquarium. You can easily rent a car at Key West International Airport for added flexibility when travelling around the islands, however Hyatt Centric Key West charges a $20-a-night parking fee for guests.

For budget vacations in Key West:

Fairfield Inn & Suites by Marriott Key West is one of the few hotels that also offers free breakfast with your nightly rate. Easily hop on the trolley which stops in front of the hotel for a new vantage point of the city when traveling between different locations on the island or to Key West International Airport.

Eden House and Suites is a 4-star guest house in the old city that prides itself on old-fashioned customer service coupled with modern comforts to help you find your home away from home. In addition to a heated pool, Eden House also offers guests waterfalls, hammocks, swings, and a garden café on-site.

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Learn how to easily plan your dream trip to Florida!

20 Best Things To Do In Key West, FL You Shouldn’t Miss

January 6, 2022 //  by  Florida Trippers

There are so many exciting and unique things to do in Key West, Florida. This town is found at the southern tip of the Florida Keys and is known for its nightlife, entertainment, and relaxing island vibes.

Driving down from Miami to Key West is one of the best Florida road trips . You will pass many beautiful sights along the way!

Planning your trip to Key West last minute?

Make sure to book ahead! Hotels and tours often sell out the closer you get to your trip. Here are our top picks for Key West!

Top Experiences And Tours In Key West:

• Dolphin Watching And Snorkeling Eco Tour (Top pick!)
• Schooner Sunset Sail (2 hours)
• Reef Snorkel From Key West (Includes breakfast and mimosas)
• Hop-On Hop-Off Trolley Tour (Great way to see the city)

Top Places To Stay In Key West:

• Margaritaville Beach House Key West (Modern mid-range)
• Blue Marlin Motel (Affordable in downtown)
• Hampton Inn Key West (Waterfront with pool)
• Wicker Guesthouse (Great location!)

Along with a party atmosphere, Key West offers a lot of history and adventures. Whether you are here for a day trip , weekend getaway , or even longer, there are plenty of fun Key West activities to keep everyone entertained.

Are you a history buff? Explore the home of a great American author or the winter getaways of former U.S. Presidents! Maybe you want to live life more on the edge? Key West is filled with dives and rentals that will keep you going!

This Florida beach town is perfect for everyone in the family, and this list will help you decide what to do in Key West, Florida!

If you are looking for places to stay in Key West, there are a ton of cute Airbnbs and hotels that range from budget to luxury !

Before you plan your trip, make sure to check out The Best Times To Visit The Keys where we break down each month and talk all things weather!

Get a Drink on Duval Street

It’s not a trip to Key West if you don’t spend time on Duval Street! This lively and colorful area is one of the most popular things to do in Key West for adults.

Make sure to check out the best bars and nightlife in Key West!

This is the best place in Key West to take in some sights and enjoy local food and drinks. You will also enjoy the sounds of live music and street performers while you embrace the city! This is truly one of the Best Places To Stay In Key West!

The bar crawling scene is notorious on Duval and is a great way to spend a day or two. Even if you don’t drink, you can come for the fun atmosphere. Hanging out on Duval Street is easily one of the best things to do in Key West at night .

Sloppy Joe’s Bar is a staple in Key West and is a great stop for a drink or history. It has been around since 1937 and many famous people have ordered a drink here. It was allegedly Ernest Hemingway’s favorite bar. They even have a “Papa” Hemingway look-alike contest every year.

Book Here: Key West: 2.5-Hour Duval Street Pub Crawl

Celebrate Sunset at Mallory Square

Mallory Square is one of the most notable Key West attractions! This location is famous for its beautiful Florida sunsets and is the perfect place to unwind from your busy day.

Located on the water in the Old Town, Mallory Square is full of family fun. The Square has shops and restaurants that the whole family can enjoy!

The fun doesn’t stop there! While you’re walking through the Square, you will enjoy the entertainment of musicians and street performers, and you can even buy something unique from a street vendor!

Make sure to come for the nightly Sunset Celebration. This tradition has been happening for decades and should not be missed! Crowds fill the Square to watch the sun sink over the Gulf and watch street performers such as jugglers and magicians. This is one of the best free things to do in Key West !

Tour Harry S. Truman’s Little White House

You can learn a little bit about American history by stopping into Harry Truman’s Little White House. This is Florida’s only presidential museum and is one of the best places to visit in Key West for American history.

The home was built in 1890 and was originally used as housing for naval officers. During his presidency, Harry Truman used this house in Key West as his winter getaway when D.C. got too cold to bear. He use the house from 1946 through 1952.

It may be named after President Truman, but he is not the only president to seek the warm weather of Key West. Presidents Taft, Eisenhower, Kennedy, Carter, and Clinton have all visited as well.

For $20 per adult and $10 per child, you can tour the house and the grounds and see how the presidents lived while they were visiting Key West.

Book Here: Truman Little White House: Key West

Visit the Ernest Hemingway House

Another place to visit in Key West for history buffs is the Ernest Hemingway House and Museum. Nestled just a block from Duval street, the Hemingway House is a great way to take in some beauty and local history.

The beautiful Spanish Colonial-style mansion is full of the famous writer’s personal items, historic furnishings, photographs, paintings, and more. This is a must-see Key West destination for anyone who loves history, architecture, or literature. Make sure to put this on your list when doing a Florida Keys Road Trip!

Hemingway and his wife were gifted the home in 1931 from his uncle-in-law. They lived here from 1931 to 1939 and the deed stayed in his name until his death in 1961.

As you walk through the grounds, you will see stunning decor, lush gardens, and even some feline friends prowling around! These famous cats are descendants of cats that roamed the grounds while Hemingway himself lived in the house. Interestingly, they all have six toes like their ancestors.

Book Here: Key West Conch Train Tour

Find Great Views at the Key West Lighthouse

If you’re going to pop into the Hemmingway House, you might as well cross the street and take in the sights at the Key West Lighthouse and Keeper’s Quarters Museum!

Lighthouses always bring an extra bit of history, and this one is no exception. This black and white structure was built in 1848 to protect ships from the surrounding shallow water and coral reefs.

If you take a tour of the lighthouse, you will learn about the first lighthouse keeper, who was a woman, and you will see historic photos from when the lighthouse was operational.

Climb 88 stairs to the top of the 65-foot lighthouse to be greeted by amazing sights. You will have a 360-degree view of the island of Key West and the surrounding ocean! Don’t forget your camera!

Dive to Discover Vandenberg

Key West is one of the best places in Florida for scuba diving . One of the most stunning dives you can take is down to the Vandenberg.

This retired Navy ship was sunk seven miles off the coast of Key West in 2009 to become an artificial reef to help aquatic wildlife. The skeletal ship can be explored 150 feet below the surface if you have an up-to-date scuba certification.

The ship is found in the Florida Keys National Marine Sanctuary which offers many other places to dive. You can find North America’s only coral barrier reef and many shipwrecks. Some attractions are not as deep underwater as the Vandenburg and can be explored by snorkeling if you are not scuba certified.

Book Here: Key West: SNUBA Experience

Admire Wildlife at the Key West Butterfly and Nature Conservatory

The Key West Butterfly and Nature Conservatory is one of the best things to do in Key West with kids who love animals and nature. This is truly a tropical paradise that will cause visitors of all ages to gaze in wonder.

If you like butterflies, this place will be your heaven! There are between fifty and sixty species of butterfly housed here and over twenty species of exotic birds. Stroll through the climate-controlled, enclosed habitat and try to spot as many creatures as possible.

The conservatory has a learning center where you can learn all about the butterfly’s anatomy, life cycles, and migratory patterns. There is also an art gallery where you can see tons of art inspired by the butterflies and birds of the conservatory.

The Nature Conservatory is located right near Duval Street and is in the heart of Key West.

Taste Test at Some Rum Distilleries

Key West is known for its rum and the Rum Runner is said to be the island’s official drink. This cocktail dates back to the 1950s and is named after the rum runners who would illegally bring alcohol to the U.S. during Prohibition.

If you are interested in the production of rum, or just drinking it, there are actually three locations in Key West that may be of interest. Key West’s First Legal Rum Distillery, Papa’s Pilar, and Key West Distilling are all excellent places to pop in and learn about the distilling process of delicious rum and other liquors.

Each distillery has its own unique taste, so you have to tour each one, right? These distilleries are also a great place to learn how to whip up some new recipes!

Take a Day Trip to Dry Tortugas National Park

If you have the time, taking a tour to Dry Tortugas National Park is worth it! Exploring Dry Tortugas is definitely one of the most unique things to do near Key West. If you love checking off the U.S. National Parks , make time for this activity.

Technically Dry Tortugas is not on the island of Key West. It’s seventy miles off the coast, and while it’s not the easiest excursion to get to, it is so worth the trip.

Once on the island, you are free to explore the grounds, relax by the beach, and even go snorkeling! It is a fantastic opportunity to take in history and adventure at the same time!

The biggest attraction of the park is Fort Jefferson, which was built between 1846 and 1875. Take a guided tour to learn the complete history of this place and see how soldiers lived.

Unfortunately, visiting Dry Tortugas is not the cheapest or easiest thing to do. To get here, you have three options.

You can take the ferry for $190 per adult and $135 per child. The seaplane is the fastest and most scenic option, but it will set you back anywhere from $361 to $634 per person depending on how long you plan to stay. You can also charter a boat or take your own.

If you want to stay longer than a day trip, this is one of the best places to camp in Florida .

Book Here: Dry Tortugas National Park Day Trip by Catamaran from Key West

Learn at the Coast Guard Museum

American history can be found all over Key West, especially tied into the ocean. One of the best Key West activities to entertain history buffs is the U.S. Coast Guard Cutter Ingham Maritime Museum.

Take a tour of the Coast Guard Cutter Ingham and learn all about what life was like on board while it was in service and after. This ship was in service from 1936 to 1988 and helped save lives during both World Wars.

You will be immersed in testimonials from those who served aboard. You will also see equipment, weapons, and uniforms used by the servicemen at the time.

Step Back in Time at the Audubon House and Tropical Gardens

The Audubon House is a beautiful historic site, allowing us to catch a glimpse of the wealthy lifestyle of the mid-1800s. Built by Captain John Huling Geiger in 1840, the home was made to fit his family’s wealthy lifestyle in the heart of Key West.

In 1958, the house was saved from demolition and renovated to reflect its heyday. The house has become a beautiful destination for tourists to enjoy. Inside, you will find decor and art dating back to the home’s beginnings.

The outside is just as intriguing as the inside. The gardens are landscaped with picturesque flowers and greenery. Stroll the winding paths and admire the blooming flowers and tropical plants.

Book Here: Key West Historic Homes and Island History – Small Group Walking Tour

Stroll the Historic Seaport and Harbor Walk

Taking a walk down the Historic Seaport and Harbor Walk is one of the top things to do in Key West because there is so much to experience along the way. The seaport is lined with restaurants and happy hour’s to enjoy. There are also great gift shops and picturesque, Instagram spots.

If you make your way down the Harbor Walk, you are sure to find fishermen coming in with their catches of the day and some of the expensive private boats parked by wealthy people from around the world.

This area has been a cultural and economic hotspot for almost two hundred years! This is a great place for a relaxing walk away from the larger tourist crowds, even more so when you are taking in the sunset! Bring your significant other for one of the most romantic things to do in Key West for couples

Rent a Kayak or Jet Ski

Seeing Key West from the water is such a fun experience, and it can be yours with a simple jet ski or kayak rental. You are in Florida; you have to get out on the water!

If you prefer high-octane water sports then there are a variety of locations you can choose from to rent jet skis and tour around the island. Get your heart pumping as you zoom through the bright, blue ocean water.

Kayaking is also a popular way to explore the surrounding ocean waters. Take a solo or a tandem kayak beyond the break of the waves and enjoy a relaxing day out on the water. This is a great way to spot wildlife as well. There are also guided tours to take that are both entertaining and informative!

Book Here: Key West: Jet Ski Island Tour with Free Second Rider

Book Here: Florida Keys: Key West Kayak Eco Tour with Nature Guide

Enjoy Nature at the Key West Garden Club

The beautiful grounds of the Key West Garden Club are stunning for so many reasons.

This garden has the goal of teaching guests about tropical gardening. You will be amazed as you along the brick paths and through gorgeous courtyards all the while surrounded by amazing greenery and colorful flowers. There is a pretty water lily pond and waterfall as well.

Within the garden, you will also find the West Martello Tower. Built in 1862 during the Civil War, this tower is now listed on the U.S. National Register of Historic Places.

The Garden Club also sits right near Higgs Beach. The edges of the gardens overlook the ocean making for a serene experience.

This attraction is great for the wallet, too, because this is one of the best free things to do in Key West, Florida!

Take an Old Town Trolley Tour

Old Town Trolley Tours have always been a popular way to take in scenery and history while traveling.

Luckily, Key West has implemented Old Town Trolley Tours into their city so you can see all of the hidden and not so hidden gems this city has to offer!

The trolley is a great way to see a lot of the city without having to walk all over, especially in the Florida heat. If you have kids, this is an easy way to see the city without fear of them getting lost or tired.

If you want to add a bit of a spook factor to your trip, take the trolley after dark when it transforms into the Ghosts and Gravestone’s Tour where you can learn about the creepy history and present of Key West!

Book Here: Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Book Here: Ghosts & Gravestones Tour of Key West

Dine at Sunset Pier

Sunset Pier is one of the best restaurants in Key West , not just for the food, but for the view!

Located at the Ocean Key Resort near Mallory Square, Sunset Pier is everything you can expect from Key West. Dine at a colorful table right on the pier and look out over the water.

They do not take reservations, so make sure you get there in time to snag a seat for the sunset. The seafood is delicious, especially the seasonal oysters!

Since it is part of the resort, there is much less bustle than at Duval Street or Mallory Square, but the atmosphere and views are everything you would expect from Key West!

Take a Selfie at the Southernmost Point

One of the best attractions in Key West is the one that can only be seen here. Did you know Key West is the southernmost point of the continental U.S.?

At the corner of South Street and Whitehead Street, you’ll find a big, brightly colored buoy that marks this claim to fame. The buoy was placed in 1983 and has been a popular tourist spot since. If you want to take a picture with the monument, make sure to get there early because the line can get long.

There are also plenty of other things to do in this area. Take a picture of the Southernmost House Hotel with its pretty, pastel colors or eat at one of the nearby restaurants.

Book Here:  Key West: History and Culture Southernmost Walking Tour

Try Key Lime Pie

You cannot come to the Florida Keys and miss an opportunity to eat some genuine key lime pie! No one knows exactly when or where this Southern delicacy was first created, but the first written recipe dates back to the early 1930s.

Key West offers the perfect climate for growing key lime trees and the famous pie is the signature dessert here. Almost all restaurants have some sort of version for you to try. If you want to do a tasting to find your favorite, you can check out our list of best places to get key lime pie in Key West .

Key lime pie is a light and refreshing dessert with a crumbly graham cracker crust and a fluffy, sweet, and tart filling. Pie is not the only way to enjoy key limes. You can try key lime ice cream, fudge, cocktails, and more! Satisfy your sweet tooth with the best of Key West desserts!

Book Here:   Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

Explore Fort Zachary Taylor Historic State Park

Fort Zachary Taylor Historic State Park at the southern tip of the island is one of the best activities in Key West for the whole family. If you have the time, this is an awesome place to spend a couple of hours relaxing.

Explore the Civil War-era Fort Zachary Taylor and learn about the significance of this location. Come for one of the monthly historic reenactments to see history come alive.

The beach here is one of the best beaches in Key West , especially for snorkeling. Just off the beach, you will find amazing tropical marine life. Don’t have snorkel gear? You can rent some at Chickee Hut Beach Rentals. You can also get umbrellas, chairs, and rafts here.

Bring water shoes to protect your feet from the coral beach. This is a great place for fishing and birdwatching, too. Stop by the Cayo Hueso Café for a snack.

Relax at Smathers Beach

If you want more beach time, head to Smathers Beach . While it is a manmade beach with imported sand, it is just as beautiful as any of the natural beaches in Florida .

This is the largest beach in Key West and has a half-mile of soft sand. This beach is known for its clear water and calm waves. It is the perfect place to swim with your kids. This is also a great place for snorkeling , parasailing, and playing beach volleyball.

This beach is free to access, so it should be on your list of best places to go in Key West if you are looking to save money. Bring a picnic to enjoy at one of the tables.

Don’t forget to check out our list of the Best Florida Keys Beaches for some more ideas of places to visit!

There are so many fun things to do in Key West that everyone can enjoy! It’s a location rooted in fun and relaxation, so it is virtually impossible not to have a good time!

There is history and adventure sprinkled throughout all of Key West. That coupled with the natural beauty of the island is what keeps tourists coming back year after year.

Add some of these locations to your list of places to visit in Florida and your next trip will surely be a vacation you will never forget.