Back in 2008, married couple Deb and Dave cycled the continent of Africa for Tour d’Afrique. Although they had been traveling as a hobby for a while, the ride turned out to be the catalyst for launching ThePlanetD, their award-winning, highly influential (Forbes named it one of the Top 10 Travel Influencers in the world) blog. Since then they’ve made their hobby into a living and have been inspiring adventure throughout the 110 countries they’ve visited and beyond. Follow their adventures on YouTube and Instagram

This comprehensive guide to the best things to do in Key West, Florida takes you from traditional sites like Mallory Square and Duval Street to some of the more unique, and lesser-known attractions in Key West. 

But wherever you end up visiting in Key West, you won’t be able to escape the island feel: Key West’s proximity to Havana gives it a particularly Caribbean vibe. The southernmost point of the United States is located here and it is only 90 miles from Cuba. To read the full article from The Planet D click here!

Day 1

9:00 AM Go to the southernmost point 

A visit to Key West isn’t complete without a stop at one of the most popular Key West attractions, the southernmost point of the United States mainland. Head over there early in the morning to miss the swathes of people taking selfies at the southernmost point buoy.

The cement marker is located on the southernmost point of the continental United States. Colorful painted lines and informative text lets you know just how close you are to Cuba.

12:00 PM – Eat Key Lime Pie

Whether you’ve got a sweet tooth or prefer your treats savoury, you can’t go to Key West and not taste Key Lime Pie. It was invented here and you’ll never have one that tastes so good as in its birthplace. One of the best places to try Key Lime Pie is Kermits. You may even find the owner, Kermit himself standing outside on the corner. There’s often a line, but never fear you won’t go hungry as there are plenty of places in Key West to try Key Lime Pie.

2:00 PM – Take a cycling tour 

a group of tourists cycling key west

This cycling tour of the Key West will take you through Old Town, the Southernmost Point, Mallory Square, and on to the renowned Key West Cemetery allowing you to ride along to the cemetery with a guide. Similar to the LaFayette Cemetery of New Orleans, the Key West cemetery has above-ground vaults. One of the most notable tombs is a memorial to the U.S.S. Maine which was blown up in Havana Harbor in 1898. If you want to continue with the spooky side of Key West be sure to check out the Ghosts and Gravestones tour. Not for the faint of heart!

5:00 PM – Visit Mallory Square

Take a walk down to the waterfront and enjoy seeing many of the top Key West attractions here: The Maritime Museum, The Waterfront Playhouse, Key West Shipwreck and Treasure Museum, and the Memorial Sculpture Garden. The old town of Key West is filled with historic structures and a great way to explore the history of Key West is on the waterfront. We love walking along the water and the Historic Sea Port has a beautiful boardwalk to take in the yachts and boat charters.

After getting a feel for the area in the early evening, make sure you stay put as it doesn’t get much better than watching the sunset from Mallory Square. How do I know this? All you have to do is look at the crowds! Every evening, a sunset celebration takes place as people gather in Mallory Square. Prepare to be dazzled by street performers who make a living putting on shows for the heaving throngs in the large square. Be sure to bring some small bills or change to tip the performers, they work hard for their money.

Day 2

9:00 AM – Ride the Conch train

an image of the conch train filled with tourists in key west

Looking for a guided tour that’ll help you find your bearings on your second morning? You may want to hop on the Conch Train. It gives you a good overview of Key West neighborhoods and highlights.

12:00 PM – Visit Ernest Hemingway’s home

From 1931 to 1939 the renowned writer Hemingway called Key West his home. A surprising highlight of the Ernest Hemingway house is the Hemmingway cats. They’re dotted all about the place and each cat is said to be a descendant of the six-toed cats that Hemmingway had as pets. Check out their paws, they really do have 6 toes!

3:00 PM – Go parasailing over the Florida Keys 

a mother and child parasailing in the caribbean in key west

The first time we ever tried parasailing was here in Key West and it was so much more fun than we ever expected. Parasailing is the perfect way to see Key West’s beautiful coast as you get a stunning birdseye view of the land. 

7:00 PM – Take a sunset cruise 

Thought the sunset experience at Mallory Square was one to top them all? Just wait ‘til you experience sunset while cruising on a schooner. You’ll see Fort Zachary Taylor, the Sand Key Reef, Mallory Square, and Sunset Pier from the deck of this from one of the finest boats on the schooner fleet.

Day 3

9:00 AM – Take to the water on a kayak or paddleboard

a couple on paddleboards in key west

I didn’t even know that Key West had such an abundant wildlife refuge. It’s one of the little-known but equally amazing facts about this pocket of the globe. The backwaters of the city are a beautiful, calming place to paddle through while watching cormorants, frigate birds, pelicans, and herons fly from the trees. It’s one of the oldest wildlife refuges in the country established by Teddy Roosevelt in 1908. 

The best way to explore it is by Sea Kayaking through the mangrove forests on this 4-hour eco-tour that includes kayaking, snorkeling, dolphin watching, and light snacks.

5:00 PM Pedal the Key West Hydrobikes 

After your animal adventure and a well deserve rest back at your accommodation, head out to catch the sunset on a tour with Key West Hydrobikes. Like everything in Key West, drinks flow freely, so you can even bring two drinks with you to enjoy a toast on the water at sunset. The city has an open drink policy so grab a couple of rum cocktails to put into the drink holders.

8:00 PM Hit the bars and pubs

On your last night, it’s time to let your hair down. It’s no secret that Key West was made for partying. Once the sun goes down, you’ll be hard-pressed to find a sober tourist, especially downtown in the party district. 
Duval Street is the main bar and nightlife street and bar hopping is a way of life when visiting the Keys. If you want to join a tour of Duval Street to see the top bars and restaurants while making new friends, check out this fantastic pub crawl tour that stops at 5 top-rated pubs with a cocktail at each stop. And you will get the T-shirt to boot!

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