Key West

SleepAfloat’s Top 25

If you’re looking to have fun in Key West but don’t know where to start check out our list of the best things to see and do around the island. This list doesn’t even represent half the things the island has to offer, but it’s a good place to start! Please feel free to share with us any of your favorite activities that you’d like to see added to our list.

1. Hit the Beach
Life’s a beach so enjoy it! Spend time lounging around the private beach at our marina Key West Harbor Yacht Club or head on over to Fort Zachary Taylor State Park for the best swim spot on the island. There is an admission fee but it’s the ultimate spot to swim, snorkel, sunbathe, and watch the cruise ships come and go. There are also beach chair and umbrella rentals, clean restrooms, and a snack bar. Higgs and Smathers Beach are also nice beaches to catch some rays but please note Key West is not known for expansive white sand beaches. Most beaches are a bit rocky so bring water shoes if you have them.

2. Go Deep Sea Fishing
For those of you who love to fish, welcome to paradise! There’s a plethora of deep sea fishing charters available around the island for day and overnight trips. Stop by Historic Charter Boat Row to sign up with one of their many fishing charters or contact our friends at Andy Griffiths Charters who will take you to the best spots for fishing from Key West to the Dry Tortugas. Depending on the season, you’ll have the opportunity to catch a variety of tropical fish from Yellowtail Snapper, to Mahi Mahi, Wahoo, Grouper, Cobia, Amberjack, Kingfish, Sharks and Barracudas!

3. Catch the Conch Tour Train
A great way to tour Key West, the world famous Conch Tour Train is one of the island’s most popular attractions for a good reason. Climb aboard the open air mini train for a 90-minute tour around Old Town that is both fun and educational. Hop off at one of their many stops along the way to explore a little further on your own or sit for the entire ride start to finish.

4. Hop on the Ferry to the Dry Tortugas
Take a day trip to The Dry Tortugas National Park, located 70 miles west from Key West. Accessible only by ferry or seaplane, you can spend the entire day exploring Fort Jefferson, the park’s picturesque blue waters, coral reefs, marine life, and the vast assortment of bird life that frequent the area.

5. Discover a Natural World of Wonders
Take a journey into the world of the native plants and animals of the Keys at the Eco-Discovery Center. Fun and educational, you’ll leave with an increased appreciation for the South Florida ecosystem.

6. Make a splash!
Get in the water! Key West has terrific spots for snorkeling and diving. Explore the many reefs and underwater shipwrecks accessible to visitors by land or sea.

7. Celebrate Sunset in Mallory Square
You can’t visit Key West and not experience a sunset at Mallory Square. A big draw for tourists, the square at sunset is full of street performers from jugglers, to wire walkers, guys made up like robots, magicians, and singers all performing for visitors as the sun sinks slowly over the horizon. Local artisans also set up shop here selling their own handcrafted knickknacks.

8. Experience a Key West Sunset
Sunsets in Key West are spectacular. After you’ve experienced Mallory Square, check out the many other great spots for amazing sunset views. The La Concha Hotel rooftop bar (free, open to non guests) is a great spot for a sunset viewing with its wrap around viewing deck and panoramic views as well as the Sunset Pier at Ocean Key Resort. Sunset Pier has waterfront seating and if you go early grab a table towards the end of the pier for an amazing view of the sun melting away into the horizon. Of course our boats’ roof decks are our favorite spot to relax, with drink in hand of course, as the day comes to an end.

9. Crawl Duval
All roads lead to Duval Street. Filled with shops, restaurants and bars, this is the main drag on the island and tourist central. Always busy, it’s a great walk from one end to the other, drunk or sober!

10. Visit the Hemingway House and See a Six Toed Cat
You don’t have to be a fan of Ernest Hemingway to enjoy a visit to his Key West home. This impressive house offers a great look into the life of the famous author and what life was like in Key West back in his days. Please Note: If you are allergic to cats you might want to stay away as there are about 40 cats living at the Hemingway House, all descended from Ernest Hemingway’s cat. Most have six or seven toes on their front paws. All of them are named for movie stars.

11. See a drag show
Ready to be entertained? Take in some of the best drag shows around at one of our many gay-friendly bars like La Te Da, Bourbon Street, Bobby’s Monkey Bar or Aqua. It’s sure to make your night a little more interesting.

12. Visit our Famous Watering Holes
Spend an evening at one of Key West’s famous watering holes. You’ll enjoy cooling off with a tropical drink at Margaritaville, Sloppy Joe’s, Captain Tony’s, Schooner Wharf Bar, Hog’s Breath and The Bull & Whistle just to name a few.

13. Tour the Key West Shipwreck Museum
A great spot to take the kids, the Key West Shipwreck Museum is an interactive museum that will take you back in time as you discover Key West’s unique maritime heritage and how it became the richest city in the United States.

14. Catch Some Air
Put on a jetpack and take flight with Flyboard Key West! Take a one-on-one lesson and experience the exhilaration of flying above the water!

15. Eat Key Lime Pie
After you’ve eaten all the delicious local grub you can handle, you’ll want to wash it all down with a refreshing piece of key lime pie! Key West is known for our decadent Key Lime Pie (yellow not green). Chocolate lovers will love it dipped in chocolate!

16. Throw a Coin in the Fish Mouth at Capt. Tony’s
Capt. Tony’s a favorite hangout for Ernest Heminway, Tennessee Williams, Shel Silverstein and Jimmy Buffet is not just a bar but a piece of living history. It is believed that if you throw a quarter into the mouth of the fish, good luck will follow you until you leave the island.

17. Spend Time with Butterflies
A truly unique experience, the conservatory is home to hundreds of butterflies, a variety of exotic birds and native plants. Visitors can walk amongst the beautiful indoor gardens with colorful butterflies flitting all around. If you’re lucky one might even land on you!

18. Visit the Dead
The Key West Cemetery is a rather interesting spot to visit. Pick up a pamphlet when you enter the main entrance and it will point out all the interesting plots you’ll want to stop by. See humorous tombstones such as the one for B.P Roberts which reads, “I told you I was sick.”

19. Climb the Key West Lighthouse
Climb the 88 steps up to the top of the historic Key West lighthouse for a spectacular view from above.

20. Find Nancy Forrester’s Secret Garden
Artist and environmental activist Nancy Forrester has been rescuing abused and orphaned parrots for 25 years. She gladly welcomes nature lovers to the Secret Garden to interact with endangered South & Central American macaws and other parrots. Nancy hosts a presentation between 10 to 11 AM where guests can take pictures of uncaged birds, hold them and ask questions.

21. Take a picture at the Southernmost Point of the United States
Don’t forget to stop by and take the obligatory photo at the Southernmost Point of the USA (corner of South & Whitehead Streets). It will only take a few minutes but it’s a must do.

22. Kayak the Mangroves
Rent some kayaks from the marina clubhouse and take a cruise around the mangroves. If you’re lucky you may even spot a manatee!

23. Get Up
Soar the skies on a biplane! Explore Key West from above, flying over our famous coral reef, shipwrecks and other interesting sites this is an experience you won’t soon forget!

24. Play a round in paradise at Key West Golf Club
If golf is your game you’ll want to stop in and play a round at Key West Golf Club, an 18 hole, 6,500 yard course, designed by golf legend Rees Jones.

25. Take a walk
Put on your walking shoes and join one of Key West’s walking tours – Ghost Tours of Key West, Parrothead Tour, Bar Stroll, Scavenger Hunt, Historic Sites Tour, etc. There’s a tour to fit everyone’s interests.

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