29 Ways To Spend Your Extra Day This Leap Year In Key West: The Absolute Best Things to Do in Key West

Leap Year means an extra day that you could be lazing in Key West. From iconic bars to water excursions, historic sites, and the best eats on the island, we’ve put together an epic list of 29 ways to spend your 29 days of February in the Conch Republic. Here are the absolute best Key West activities and things to do to get to know the island town that’s second to none.

[Plan the Perfect Valentine’s Day Date in Key West]

1. Join the Mallory Square Sunset Celebration

Key West celebrates the sunsets daily at Mallory Square with live music, jugglers, and other live acts working the crowd. It’s an all-out party that draws quite the gathering. See if you can spot the “green flash,” a phenomenon that happens the moment the sun sets into the horizon. As scattered light disperses into the atmosphere, the sun’s top half may appear to flash green for just a few seconds. Mariners believe it to be a sign of good luck!

2. Walk Down Duval Street

Running straight through Old Town, Duval Street is a historic strip of debauchery and fun. You’ll find plenty to do in the “unofficial” downtown of the Conch Republic, whether it be imbibing at some of the most popular watering holes or simply sauntering for the spectacle of it. During the day, stop by the Key West Butterfly & Nature Conservatory (more on that below) or the San Carlos Institute for a fascinating look at Key West history.

3. Have a Drink at Sloppy Joe’s Bar

The famous (and infamous) saloon was Ernest Hemingway’s favorite bar on the island, beloved for its off-beat ambiance and friendly crowd. Today, it still has those old time charms, except with a much, much bigger crowd. Order a daiquiri, Hemingway’s favorite. Honorable mention: Captain Tony’s Saloon, Hog’s Breath, and Green Parrot Bar are all historic Old Town dives worthy of your time.

4. Walk Along the Key West Bight at the Historic Seaport

The Bight has a boardwalk that hugs the shore and is packed with shops, popular eateries, and live music and events nearly every night of the week. Notable stops include Half Shell Raw Bar, Schooner Wharf Bar, The White Tarpon Bar & Restaurant, and Conch Republic Seafood Company.

5. Seek out the Native (and Non-Native) Animals

The Florida Keys are home to a unique subspecies of many animals. By land or sea, keep an eye out for native species like dolphins, loggerhead sea turtles, and mangrove buckeye butterflies, and even non-native species like iguanas and roosters (somewhat a mascot for Key West!).

6. Sip a Key Lime Pie Martini

In Key West, we also take our key lime pie in liquid form. Try Sloan’s Key Lime Pie from Rum Row, located next door to 24 North Hotel. The dessert cocktail is made with Key West First Legal Rum, fresh key lime juice, a dash of condensed milk, cardamom liqueur, simple syrup, and a fresh egg. The really interesting aspect is the dollop of whipped cream and crushed graham cracker and Captain Crunch rim, which finishes off the pie experience perfectly. Honorable mention: There are a lot of places to sip brews you’ll only find in Key West. Try the Waterfront Brewery for craft beer and Key West Legal Rum for spirits (there’s Cuban Coffee Rum, Coconut & Pineapple Rum, and even Key Lime Rum).

7. Order a Plate of Conch Fritters

You’ll find this dish at nearly every seafood restaurant on the island, and for good reason. The battered and deep fried dough balls with spices and ground conch are just a part of island life. Honorable mention: Key West pink shrimp, grilled Florida spiny lobster tail, seafood ceviche, and smoked fish dip are all top seafood dishes here on the island as well.

8. Explore the Hemingway House & Museum

The stately Hemingway House & Museum on Whiteland Street in Old Town is a big draw for those visiting Key West. When touring the author’s former home, make sure to see the gigantic 65’ long cerulean pool out back (the first residential one on the island and still the largest) and pet the six-toed Hemingway cats that roam throughout the garden.

9. See Key West’s Gigantic Tarpon

At nearly every marina on the island you’ll see the massive “Silver Kings” lurking below the docks, waiting for fish scraps discarded by the fishermen above. There’s even tarpon feedings. The boardwalk outside A&B Lobster House on the Bight is a great place to start.

10. Stroll through the Harry S. Truman Little White House

Florida’s only presidential museum has hosted inventor Thomas Edison, scientist Edward Hayden, and six American presidents, the most important being Harry S. Truman, who spent 175 days of his presidency there from 1946 through 1952.

11. Visit the Key West Butterfly and Nature Conservancy

Always a top attraction in Key West, the Duval Street conservancy houses hundreds of free-flying butterflies, exotic birds, and flamingos inside its glass-domed habitat. It’s truly a magical experience to walk among 50 to 60 different butterfly species from around the world.

12. Browse the Tennessee Williams Key West Exhibit

The great American playwright (A Streetcar Named Desire, Cat on a Hot Tin Roof, and The Glass Menagerie) and Pulitzer Prize winner Tennessee Williams lived in a cottage on Duncan Street from 1949 until his death in 1983. Visit the museum at 513 Truman Ave. to get a better understanding of the introverted writer. Artifacts on display include his old notebooks, a typewriter, photos, newspaper clippings, and more.

13. Take a Picture at the Southernmost Point Buoy and Mile Marker Zero

The anchored concrete buoy at the corner of South and Whitehead Streets marks the southernmost point in the continental United States, with Cuba only 90 miles beyond. Get there early, the buoy always has a long line of people waiting to take a picture with the 12’ tall structure. Take the walk up Whitehead Street afterwards to see Mile Marker Zero at the corner of Fleming Street. Honorable mention: Another popular photo op is at Fort Zachary, where you’ll spot the iconic, wooden directional signs.

14. Lay Out at Smathers Beach

The largest public beach stretches along New Town and is just a few miles from 24 North Hotel. It’s long, sandy, lined with coconut palms, and offers excellent views of the Florida Straits. Honorable mention: Of course, there’s no bad beach in paradise. See also Fort Zachary Taylor State Park Beach and Higgs Memorial Beach Park.

Want to get out on the water? In Key West, a day out on the water is always within reach. Book your hotel stay in advance at 24 North Hotel.

15. Rent a Golf Cart

24 North Hotel’s shuttle delivers you straight to Old Town, but for a quick jaunt around the historic neighborhood, consider renting a golf cart. They’re a blast to drive, plus it’s a great way to split the cost of a fun excursion with friends. Check out Fury Water Adventures for their golf cart rentals.

16. Play Key West Bingo

We’ve included this fun activity in the list because it’s something you can take with you, even if you leave Key West! It’s simple, stream Sloppy Joe’s real-time street cam online and fill out the digital bingo card (link below). Bingo squares include actions like seeing someone “skateboarding,” giving a “high five,” and “dancing.” Key West Bingo is at its most fun when done with a group.

17. Grab a Cup of Coffee at Cuban Coffee Queen

Islanders take their Cuban coffee seriously, and there’s no better spot for authentic Cuban coffee than Cuban Coffee Queen. There’s three locations to choose from to get cups of pure energy. Their Café con Leche and Cuban Frappe are always popular. Plus, their iced coffee drinks are on another level, as the ice cubes are made entirely of coffee.

18. Shop for Key West Souvenirs

Don’t leave Key West empty handed. Shop mementos exclusive to Key West like cigars at Rodriguez Cigars, handmade sandals at Kino Sandals, and everything key lime at Kermit’s Key Lime Shoppe (where you’ll find key lime scented/flavored bath products, gourmet food items, seasonings, pies, and so much more).

19. Go Scuba Diving

Dive below the surface to see North America’s only coral barrier reef. Coral reef habitats and wrecks located just miles offshore are all swimming with activity. 24 North Hotel’s Dive then Dream Package includes a 20% discount on all dives and excursions with Southpoint Divers, a reef-safe suntan lotion, and a convenient drop off just one block from Southpoint’s Old Town shop.

20. Go Fishing

The Keys are home to abundant sources of fish and a variety of species. No matter the season, there’s always fish. Grab a fishing permit and hook a marlin, swordfish, dolphinfish, snapper, spiny lobster, stone crab, and more from the shores or deep within the Florida Straits on a fishing charter. Check out fishing restrictions ahead of time.

21. Take the Ferry to Dry Tortugas National Park

Dry Tortugas National Park is made up of seven small islands about 70 miles west of Key West, accessible via daily ferry from the Bight. The ride out is just over two hours, and visitors typically spend the four hours on Garden Key, checking out the civil-war era Fort Jefferson and snorkeling the pristine water.

22. Visit the Smallest Bar in Key West

The 72-square foot bar on Duval Street lives up to its name. Rumor has it that they have the best rum runners on the island. Order at the tiny bar, enjoy your rum runner outside, and people watch.

23. Grab a Seat on a Cruisin’ Tiki Bar Cruise

Why go bar hopping when you can hop on a bar? Once you see one of these tiki bar boats whiz by from Mallory Square, you’ll want to hop on the next departing cruise. The 120-minute excursion glides through the water with your party seated around the bar. The bar seats six and it’s BYOB, so you can bring whatever you like.

24. Board a Catamaran for a Sunset Sail

Fury offers a sunset sail complete with live music from Key West’s best musicians, a Chef’s selection of seasonal appetizers, and drinks like margaritas, Champagne, wine, and draft beer. Save on this memorable experience with 24 North Hotel’s Fury Watersports Package.

25. Climb the Key West Lighthouse

Decommissioned since 1969, the historic 1849 lighthouse now serves as a museum and symbolic pillar dedicated to the island’s maritime heritage. Walk up the 88 steps to see the island from above.

26. Rent a Jet Ski

Jet Skis were made for those who love to travel at high speeds and explore the open water. Take a 90-minute guided tour for two on a tandem jet ski with 24 North Hotel’s Jet Ski for Less special offer. View varying points of interest from the sea while enjoying this scenic trek.

27. Paddle through the Mangroves on a Kayak

The mangrove forests of the Florida Keys are an important part of the island’s ecosystem, acting as a nursery area for coral reef fish, a nesting spot for birds, a habitat for Key deer, and a protector of Florida shorelines. Key West has plenty of them to explore. Kayak through winding mangrove creeks for a totally unexpected island experience. We recommend Lazy Dog Adventures for your mangrove kayak trip.

28. Take a Sightseeing Tour

See the best of the island in one go with the Old Town Trolley, the Conch Tour Train, or a ghost tour aboard Ghosts & Gravestones for a convenient and time-saving way to learn all about Key West, its history, and colorful characters.

29. Attend Fantasy Fest

Although this annual event takes place only in October, a list of the top things to do in Key West isn’t complete without mentioning the biggest party of the year. The 10-day extravaganza overflows with activities, mostly adults-only, although there are family-friendly events like the Zombie Bike Ride, Goombay Festival, and weird and wild Fantasy Fest Parade. The festival dates back to 1979 and draws approximately 75,000 party-goers every year.

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Leap to it. Planning a stay in Key West? Check out our best rates at 24 North Hotel. We have an on-site Starbucks, shuttle service to Old Town, and our pool area is one of the best on the island. See our special offers - including rates just for Florida and Georgia residents.