Key West's Quirkiest Themed Restaurants

Some restaurants in Key West provide far more excitement beyond what you'll find on the menu. Dine with Parrotheads, drink among airplanes, and dance to Cuban beats at these places that found a theme, and stuck to it. They’re kitschy, they’re entertaining, and they're fun! Here are the quirkiest themed restaurants in Key West.

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First Flight Island Restaurant & Brewery

Formerly the birthplace of Pan American World Airways, First Flight Island Restaurant & Brewery features a treetop terrace, garden dining, and homemade beers on tap. In 1927, the building sold tickets for the first international air service flight out of the U.S. to Cuba. Like the name, the current business recognizes its Pan Am past, complete with a “crash bar” that has a Sikorsky seaplane plunging through the ceiling. 301 Whitehead St.

Margaritaville

Since the annual “Meeting of the Minds” gathering moved out of town, there’s only one place for Jimmy Buffett’s Parrotheads to congregate in Key West - Margaritaville, where Jimmy opened his first successful retail store in 1985. The Jimmy Buffett-inspired bar and grill serves up all the island fare you’d expect, alongside themed cocktails like Last Mango in Paris, Changes in Latitudes, and 5 O’Clock. 500 Duval St.

Better Than Sex - A Dessert Restaurant

There’s no need to choose between a post-dinner nightcap and a sweet treat - Better Than Sex offers both. The sultry dessert bar in the heart of Old Town features decadent desserts and chocolate and caramel-rimmed wine, beer, and house-made cocktails in an intimate speakeasy-like atmosphere covered in lush red curtains. Tables also have privacy curtains and candlelight to set the mood. 926 Simonton St.

El Meson de Pepe’s

Located directly in Mallory Square, the kitschy, Cuban family-owned El Meson de Pepe restaurant serves up delicious drinks, eats, and live salsa music. They have a wide variety of Cuban dishes, from picadillo (savory, well-seasoned ground beef) to rabirubia frita entera (whole fried yellowtail fish). For tapas, we recommend the Cuban nachos, which are made with homemade plantain chips, ropa vieja, and picadillo, topped with guacamole and cheese. Come samba during the Sunset Celebration to the rhythm of the music and enjoy one of the most beautiful views on the island. 410 Wall St.

Santiago's Bodega

We love the concept of Santiago’s Bodega, an eclectic yet charming tapas bar whose food embodies the diversity found in Key West. Their thoughtfully designed small plates are best described as “food for the soul.” Standout dishes include yellowfin tuna ceviche in a spicy citrus juice, smoked salmon carpaccio with crostini and crème fraiche, and prosciutto and scallion cream croquettes. The whole place is bedecked in handcrafted artistry, with reclaimed wood, stained-glass, hand-laid floors, and signage made from old barn wood from Founder and Operator Jason Dugan’s childhood home. 7305, 207 Petronia St #101

Amigos Tortilla Bar

Colorful sugar skulls bedeck the walls and traditional Mexican tacos are front and center at Amigos Tortilla Bar (in nearly 15 varieties including baja fish, shrimp, and fried avocado). Except, their tortillas have a signature square shape! Amigos swears these shells are more functional and hold more filling with less spilling. Their menu also includes burritos, bowls, nachos, quesadillas, and Mexican street corn. 425 Greene St.

The Conch Republic is known for conch fritters, Key lime pie, stone crab, and other gulf water varietals. Know where to go for the freshest, local seafood, as well as and the best time of year to eat pink shrimp or spiny lobster - check out our Key West Food and Dining Guide.

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Planning a trip? Visit Key West’s newest attractions with shuttle service to and from Old Town, available to our guests. Enjoy your island getaway with a longer stay at 24 North. Now for a limited time, Stay Longer and Save More with our special deal.

Enjoy fresh eats from Toasted Coconut, 24 North’s laid-back, family-friendly outdoor restaurant located right next to the pool, slinging tropical cocktails and dishes like Conch Fritters, Smoked Fish Dip, and Blackened Mahi Tacos.