Key West is the southernmost island in The Florida Keys and is referred to as the “Conch Republic.” The rowdy town is perfect for a girlfriend getaway because of its walkability and tropical vibes. There’s always something going on, including Fantasy Fest and the New Year’s Eve Shoe Drop. Whether you’re road-tripping from Miami or flying into Key West Airport, you’ll need at least three days to fully enjoy the island.
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There’s no shortage of delicious eateries for every taste from casual cafes to award-winning restaurants that require reservations.
Blue Heaven– The former home where Hemingway hosted boxing matches is the most popular breakfast spot in town for lobster benedict, banana bread, and key lime pie. But go early since they don’t take reservations.
Moondog Cafe & Bakery– This cozy cafe is open daily with breakfast tacos, shakshuka, and French toast. There are also vegan and gluten-free pastries for those with special diets.
Firefly– The welcoming restaurant has brunch daily in the Bahama Village neighborhood with Southern-style sausage biscuits, shrimp and grits, and chicken and waffles. If you have a big group, make a reservation.
Garbo’s Grill– The a taco truck that now has a permanent location, this place serves up delicious and spicy varieties like fish tacos, Korean barbecue tacos, and Jerk chicken quesadillas.
Pepe’s Cafe– The cafe has been a Key West staple since 1909, serving omelettes, sandwiches, and steaks. Chow down on oysters and key lime pie, one of the best on the island.
Fisherman’s Cafe– The casual counter-service eatery has sandwiches and wraps with fresh local seafood as well as Cuban coffee. Grab them to go and enjoy in Mallory Square.
The Stoned Crab– The waterfront restaurant focuses on sustainable seafood like offer stone crab and a “green” cocktail menu. Enjoy the fish of the day before feeding the sharks.
Little Pearl– This neighborhood wine bar and restaurant is known for conch chowder, local snapper, and Caribbean-inspired flavors. The space is decorated in coastal decor.
Latitudes– Located at Sunset Key and only accessible by ferry, the restaurant has views of Mallory Square and a menu of seafood dishes. Reservations are required!
Key West boasts a little bit of everything, from cocktail bars to classic pubs, especially on Duval Street. If you’re not looking to imbibe, there are also coffee shops.
Cuban Coffee Queen– The quick-service shop is obviously known for its Cuban-style coffee but they also have breakfast dishes and Cuban food. Beware that they brew it strong!
Caroline’s Other Side– This bar and restaurant is a cozy spot known for its cocktails, including their Hemingway Daiquiri and authentic absinthe. They also have local craft beer.
Schooner Wharf Bar– Set around the large courtyard, this outdoor space is a popular hangout for locals with live music every night of the week and frozen drinks.
The Green Room– Built with environmentally responsible materials, the themed bar has green drinks, made with sustainable ingredients, and offers live music.
Rooftop Cafe– This space which resembles a greenhouse and has specialty martinis. If you’re looking for a rooftop bar, keep in mind that many are clothing optional. But this is one of the few that isn’t.
La Te Da– For live entertainment, don’t miss the cabaret show at this legendary gay bar, held three to four nights per week. They have both a terrace bar and piano bar.
Distilleries- Key West is also home to two rum distilleries that are open for tours and tastings. Key West First Legal Rum Distillery offers free mojito classes while Papa’s Pilar Rum Distillery is inspired by Hemingway and his boat.
Relaxing, Beauty and Fitness
Your girl’s weekend doesn’t have to be just eating and drinking. It’s also a chance to relax and catch up over a class or get yourself pampered.
Spas- There are a number of spas where you can get a massage, including Prana Spa, which also has body treatments and facials. Nailtini Nail Bar & Spa is the perfect place to get a manicure before hitting the town with complimentary drinks.
Yoga- Take advantage of the relaxation the Keys lifestyle has to offer with a relaxing day at the beach at Fort Zachary Taylor or a morning yoga class there. Key West Yoga Sanctuary also offers classes.
Bikes- The best way to see the most on the island is on two wheels. Grab a One Day Bike Rental in Key West to explore while also getting your heart rate going.
Kayaking- The area around Key West is full of mangrove forests that can be explored by kayak. Geiger Key is one of the places the trips leave from. Book your Key West Half Day Kayak Rental.
Browse the hip boutiques and offbeat stores found in downtown Key West for the perfect souvenirs.
Books & Books– There’s an island outpost of the Miami bookstore that is owned by Judy Bloom. You might even see the acclaimed author there. The staff is helpful in selecting books including bestsellers and regional history.
Tucker’s Provisions– The fishing provisions shop and general store is the perfect place to grab Keys-inspired clothing and accessories. They also have cold drinks when you need refreshments.
Key West Pottery– Visit the shop where the hand-thrown and glazed pottery is made and sold. They use incredible shades of blue that are sure to remind you of your Keys vacation.
Vignette Key West– The stylish women’s clothing store has a little bit of everything including breezy coastal attire and accessories.
This trip may not be about sightseeing, but that doesn’t mean you can’t cross a few attractions off your list during your visit.
Key West Art & Historical Society– The art museum has rotating exhibits and a collection of regional art and historic photos. There are also art galleries to browse for unique souvenirs.
Key West Tropical Forest & Botanical Garden– Explore the tropical plant life at this botanical garden that has native species as well as those found around the Caribbean.
Honest Eco Tours– This company has snorkeling and dolphin watching tours in solar-powered boats. They provide everything you need from refreshments to gear.
Sunset Sail in Key West with Cocktails and Hors d’Oeuvres– End the day on the water as well with the best sunsets in the state, enjoyed over food and drinks.
Dry Tortugas National Park Day Trip by Catamaran– If time allows, visit the country’s southernmost national park, a former fortress with mangrove forests and surrounding smaller islands.
Small-Group Key West Food Tasting and Cultural Walking Tour– Chow down on the island’s best food on a walking tour of downtown Key West.
There’s no shortage of unique places to stay in Key West, no matter your budget. You don’t have to sacrifice style and amenities at these girlfriend getaway-friendly accommodations.
Parrot Key Resort– Located outside the main area of Key West, this hotel has villas with porches, multiple pools (including an adults-only!), a bar and restaurant, and Duval Street shuttle. Read our review here.
Margaritaville Key West Resort & Marina– The fun resort takes its inspiration from Jimmy Buffet with coastal-inspired rooms with balconies overlooking the port, onsite dining, and an outdoor heated pool.
The Saint Hotel– A part of the Autograph Collection, this boutique hotel contains 36 artsy rooms with multiple beds, kitchenettes, WiFi, and an outdoor pool. There’s also a casual restaurant.
The Perry Hotel– Rooms at this hotel have balconies overlooking the water and Stock Island. Guests also have access to an outdoor pool and an area shuttle as well as a welcome drink.
This guide was created with assistance from the Florida Keys Tourism.