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Things To Do in Key West

Rediscover Key West. The ideal Staycation in the Florida Keys

Key West is one of our favorite Staycation destinations. This vibrant little island is only 4 miles long and 1 mile wide. It’s small, but there's a bunch of fun waiting for tourists from all around the world. People really get captivated by the vibrant hues of the water and the endless beaches, but there's more than just sand and palm trees here. Hotels in the keys are full of luxuries everyone can enjoy and offer incredible perks for Staycationers! 
There are always fun things to do in Key West, get the inside scoop by becoming a member of Staycation South Florida.

Key West. An Island + a city

Do you live in Florida? If you live a little further up, in the northern cities, or right smack dab in the middle where beaches are not so close to home, you can still become a member of Staycation South Florida, plan a road trip every weekend and have fun in the Keys sun whenever you want. Whenever you need some extra sun you can plan a quick getaway south in order to discover the best of Key West. 

Go ahead, take a dip in the Florida Keys! And then visit some of these exciting attractions.

Discovering Florida. 500 years of island fun

Did you know Juan Ponce de León was the first tourist to arrive at the Keys? In 1521 the Spanish explorers that arrived here were greeted by The Calusa people, a Native American tribe that populated the southwest coast of Florida. Well, it wasn't exactly a party. In fact, the Calusa weren't so happy to share their island with the explorers. They defended their beaches because they knew the island was special.

Thankfully, since then a lot has changed. Tourism and hospitality are now a must in all the pretty Hotels in the Keys. There’s lots  to do and so much to see in the Florida Keys, especially in Key West. Make sure you take the time to get to know the best sites this island city has to offer. Why not plan a weekend away from home? 

Members only: Start your Staycation by booking the hotel room with the most incredible view of Key West, right now.

So many activities. Where should you start?

We created a short list of things to do in Key West. We want to make sure you see the best of the city and we know it isn't always easy to figure out which sites are must-see attractions. Here’s an example itinerary.

What to do in Key West? 

If you only have a couple of days to enjoy the best of what the city has to offer, include these activities in your next Key West staycation.

7:00 AM Start the day off visiting the Hemingway house. 

  • Make sure you arrive early, before all the tourists hop off their cruises in order to start flocking to this popular attraction. 
  • What's so special about it? Have you read A Farewell to Arms? The novel, published in 1929 narrates a steamy love affair during the First World War and quickly became Hemingway's first best-seller. 
  • Rumor says, Ernest spent lot's of time in his house in Key West, relaxing, enjoying the sun, fishing, and writing the book that would become a high-point of American literature, along with  For Whom the Bell Tolls (1940) and The Old Man and the Sea (1952). 
  • Maybe you will feel inspired after visiting the acclaimed author’s home and start writing the next great american novel. Who knows! 

10:00 AM

Feeling nostalgic? Are you the kind of person that enjoys imagining what life was like a century ago? Take a stroll down memory lane, visit the historical district at Jackson Square. 

12:00 PM

Oh, so hungry! But the beach is waiting… Good thing you can do both. Take your lunch to Smathers Beach. Enjoy the afternoon sun and fill up your stomach so you have energy to continue exploring the island.

2:00 PM

Shop at Mallory Square. Find a cute outfit, Key West inspired fashion is all about feeling free, relaxed and enjoying the latest colorful trends. Sunglasses are a must!

10:00 PM

Time to rest. Find a great hotel with a beautiful view, book a massage and just relax! You are in Key West, life's good.  

The best part of staycationing in Key West?

You can do all this without driving a mile. The buses in Key West are a great transportation method. Grab a bus or walk around! Start discovering Duval Street from start to finish, it's only 6 km long but there's a lot to see and experience here. Eat, play, shop, discover! 


Hey, Florida!

Are you considering a Key West Staycation? You've worked hard and deserve some time off. We hope you feel inspired to book a Staycation in Key West and enjoy the best of what this city/island has to offer in order to satisfy the most demanding tourists. Start unwinding, honey. No excuses! 

Are you ready to enjoy all the perks of being a tourist in your own backyard? Receive a newsletter with all available discounts if you are a Florida Resident. Become a member of Staycation South Florida and start enjoying every weekend to the fullest.