With its 500-year history of Spanish, Bahamian, Cuban, and American influences, Key West’s reputation as a live-and-let-live Conch Republic has long made it a home and travel destination for the LGBTQ+ community.

Here, island time and the beach lifestyle take on a new meaning flanked by the Atlantic Ocean and the Gulf of Mexico. Whether you’re a morning person who loves to kayak through mangroves or a night owl who loves to bar hop, the Florida Keys, especially Key West, allow you to indulge and be yourself.

Thanks to its subtropical weather and Caribbean-adjacent position, the Florida Keys offers beach weather year-round. That said, March through May are the best months to visit to escape the winter crowds, or the last week of October if you want to experience Fantasy Fest, a Florida tradition with a Mardi Gras-level of bacchanalianism.

Regardless of the timing, here’s what you need to know before making a trip.

What to do in the Florida Keys

As RuPaul says, “reading is fundamental.” When it comes to the LGBTQ+ community, it’s important to be cultured. Key West has long been known as a haven for artists, hippies, immigrants, counter-culture activists, and the LGBTQ+ community. For a city ripe with ribald entertainment and day-drinking opportunities, it also hosts a healthy number of cultural institutions that you should visit (a full list of dates and events can be found on the Florida Keys site). But to start, you can’t go to the Florida Keys without enjoying some time on the water.

Blu Q Catamaran: These four-hour day trips and two-hour sunset sails cater to the gay community. I joined a Blu Q trip where the friendly staff took us on an excursion to a secluded sandbar rung by crystalline blue waters where the group swam, drank, and made new friends. We then sailed farther west to a shallow area where we snorkeled and came face-to-face with a multicolored array of fish, corals, sponges, and the remnants of a shipwreck. The Blu Q crew provided water, fresh fruit, and healthy snacks, inviting guests to bring their own alcohol.

Key West, FL, USA - January 29, 2018: Terrace of La Te Da bar in Key West

Photo: Rini Kools/Shutterstock

Bar hopping on Duval Street: Duval Street is Key West’s main drag – pun intended. The blocks between Angela and Catherine Streets are festooned with welcoming rainbow flags, LGBTQ+ bars, cabarets, an LGBTQ+ Visitors Center, and the Tennessee Williams Museum. The drag queens at 801 Bourbon are known for carrying on the tradition of Southern queens: spirited, gritty, and charmingly unpolished. We caught an old-school drag show at La Te Da, which, like many establishments in Key West, is a jack of all trades type of business with a cabaret, a restaurant, and a hotel. We caught Christopher Peterson’s Eyecons, in which he impersonated Marilyn Monroe, Liza Minelli, Reba McEntire, Cher, and Judy Garland in less than two hours. The highlight of Peterson’s tour-de-force is his commitment to singing live and creating a show that will shock you with its combination of bawdy humor and inspirational coming-of-age autobiographical narrative.

Tennessee Williams Museum: A fascinating museum that exists under the radar but just half a block off Duval Street is the Tennessee Williams Museum. One of America’s most important playwrights of the 20th Century, Williams considered Key West home, living on the island for 34 years – 14 of which with his romantic partner Frank Merlo. Dennis Beaver created the museum as a tribute to the Pulitzer Prize-winning author of A Streetcar Named Desire, Cat on a Hot Tin Roof, and The Glass Menagerie. Beaver’s passion for sharing the life and work of Williams is on display in the carefully curated exhibits that don’t shy away from the highs and lows of Williams’s life. The section on the playwright’s relationship with Merlo is a must-see when so many museums avoid discussing the queer identities of the very people they claim to celebrate.

KEY WEST, Florida Keys — A cat dubbed Leonardo da Vinci rests atop an antique typewriter at the Ernest Hemingway Home & Museum on Whitehead Street in Key West, Fla. Hemingway lived and wrote at the home for most of the 1930s, penning some of his best-known works. Now a registered National Historic Landmark, the home is a museum honoring the author — and a haven for several dozen cats, many of them with six toes and descended from a sea captain’s feline given to Hemingway. (Rob O'Neal/Florida Keys News Bureau)

Photo: Rob O’Neal/Florida Keys News Bureau

The Ernest Hemingway House: This stunning piece of Key West architecture is well worth the visit to glimpse into the author’s writing studio. But make no mistake, the six-toed cats steal the show. Many a visitor can be seen wandering the property trying to photograph and pet as many of these polydactyl cats as possible. Whether it’s the whimsical bathroom tiles or the first pool built in Key West, each corner of Hemingway’s house has something to appreciate. You can take a guided tour or walk around at your own leisure.

Photo: Horacio Sierra

Key West Butterfly and Nature Conservatory: The LGBTQ-owned center is a favorite among locals and visitors alike. The climate-controlled, glass-enclosed habitat gives you a chance to come face-to-face with butterflies and birds from around the world. Don’t be surprised if while you’re watching a pair of strikingly pink flamingos perform a courtship dance, a duck waddles by your feet and a blue morpho butterfly lands on your shoulder. It happened to me. Although it’s small compared to a state- or university-run butterfly museum, the intimate nature of the conservatory invites you to lull for a good 30 to 45 minutes and immerse yourself in a lepidopteran wonderland.

Visitors stroll outside the Harry S Truman Little White House Museum in Key West, Fla. In 1946, Truman began visiting the island for rest and relaxation and returned for 175 days during his presidency. Photo by Andy Newman/Florida Keys News Bureau

Photo: Any Newman/Florida Keys News Bureau

The Little White House: President Harry S. Truman considered Key West his second home. He spent 175 days of his presidency in what is now known as The Little White House. It’s here where he strategized and drafted some of the most influential Civil Rights legislation of the 20th Century, such as an Executive Order desegregating the military. President Truman invited noted Black Civil Rights leaders such as Dr. Mary McLeoud Bethune, who founded one of Florida’s HBCUs, to be one of his advisers. The house’s collection demonstrates how much President Truman embodied Key West’s live-and-let-live attitude. One fascinating piece is the custom-made poker table he used to gamble on and its accompanying cover that hid all hints of its at-the-time taboo purpose. Other highlights include his collection of Hawaiian and guayabera shirts and a painting of the Everglades, which he made a National Park, hanging above his bed. When taking a tour of the house and learning more about Truman, it’s easy to imagine that the Midwestern boy from Missouri would have evolved right along with society thanks to his time in Key West.

Photo: Horacio Sierra

Kayaking with Tortuga Jack and Key West Eco Tours: Another reason to drive down to Key West is so that you can stop at Geiger Key and meet Tortuga Jack. A character well known in the Lower Keys, Tortuga Jack led us on an eco-minded kayak tour of the Keys’ flats. With his Santa Claus beard and witty quips, Tortuga Jack taught us about the mangroves, sponges, jellyfish, birds, and starfish that live in the unique ecosystem created by the Keys, which are built on the carbon of decomposed corals. If you’re lucky enough, he’ll recite some of his original poetry for you while you glide over the key’s azure waters.

Where to eat and drink in the Keys

Grilled shrimps in the authentic environment of a harbour restaurant in Key West

Photo: mezzotint/Shutterstock

The Docks at Stock Island: Here you’ll find an unbeatable combination of fresh seafood and gourmet preparation. Located on the docks in an out-of-the-way neighborhood, the Dock’s limited menu ensures the offerings are fresh and the chefs have perfected their skills. Baked oysters, Key West pink shrimp, tequila-sprinkled drunken scallops, delectably textured swordfish and snapper. Invite your friends and try it all. Then save room for dessert. The hand-made zeppoles, fried dough balls coated in power sugar, are rivaled only by the strawberry bread pudding topped with toasted coconut.

Cuban cuisine: Known in Spanish as Cayo Hueso, Key West is closer to Havana than Miami. After soaking in the history of Key West’s centuries-long Cuban community at the San Carlos Institute on Duval Street, you can check out two great Cuban restaurants: El Siboney in Old Town or El Mesón de Pepe on Mallory Square. Both restaurants serve healthy portions of Cuban classics such as picadillo (ground beef), ropa vieja (shredded beef), puerco asado (roasted pork), and camarones enchilada (creole shrimp). Again. Save room for dessert – especially at El Meson, where we ordered a grand triumvirate consisting of coconut flan, guava pudding, and Key Lime pie.

Latitudes on Sunset Key: If you want to splurge and live your best Oprah Winfrey life, then make a reservation for Latitudes on Sunset Key. Unless you were fortunate enough to be invited to Oprah’s 44th birthday when she rented all the cottages on the island for her and her friends, you can take a ferry to Sunset Key and enjoy a beachside meal. Freshly squeezed fruit and vegetable drinks complement hearty breakfast meals like lobster eggs benedict and key lime ricotta pancakes. Order a side of yucca hash browns for something different.

Chef Michael’s: Islamorada also offers some gourmet dining while you’re on your way to Key West. Chef Michael’s offers an array of fish that can be prepared in sundry ways. To try something unique order lionfish, an invasive species that conservationists are more than happy to see disappear, or the meaty hogfish. Another only-in-the-Keys highlight is a shrimp-and-lobster ceviche medley served in a cracked coconut shell.

Islamorada Brewery and Distillery: The best bar in Islamorada is its very own brewery. Islamorada Brewery and Distillery offers locally brewed craft beer and cocktails made from spirits distilled on site. The family- and pet-friendly beer garden is the perfect place to cool off with its tropical canopy and misting fans. Spanky’s food truck will supply you with all the fries, nachos, pretzels, and burgers you need when washing down a cool beer.

How to get to the Florida Keys

While you can easily fly into Key West’s airport with direct flights from Boston, New York, Chicago, Dallas, and DC, the most memorable and social media-worthy way to get there is by car. If you book with a car rental agency early enough, you can score one of the hundreds of brightly colored convertibles available from the Miami or Fort Lauderdale airports to cruise down the iconic Seven-Mile Bridge and visit Key Largo, Islamorada, and Tavernier Key along the way to it’s-so-gay-it’s-straight-friendly Key West.

How to get around

Although you’ll need a car to explore the other islands, measuring four miles long by 1.5 miles wide, Key West is as pedestrian friendly as it gets. Staying anywhere south of White Street allows you to walk from the Atlantic Ocean to the Gulf of Mexico in 30 minutes. Parking is in short supply, so you can hope to score one of the coveted free visitors spots on side streets or just opt for one of the parking garages near the docks on the Gulf side.

Where to stay

We hope you love the places we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay.

For LGBTQ+ visitors, Key West is about where you stay as much as what you do. Alexander’s Guesthouse is the epitome of inclusivity. Although it’s owned by and caters to the LGBTQ+ community, all are welcome. And who wouldn’t want to stay in this boutique hotel that features a heated pool, a hot tub, and multi-level sun decks? Comprised of 17 room spread out over 3 Conch-style houses built in the early 1900s, Alexander’s has been lovingly updated with modern amenities. The best feature about Alexander’s is the sense of community that’s created during its complimentary breakfasts and daily happy hours. Located off the corner of Fleming and Frances Streets, Alexander’s offers you a relaxing respite from the bars and restaurants of Duval Street, which is a quick 10-minute walk down the street. Other LGBTQ+ guesthouses such as Equator and Island House are located down the street, forming a mini-gayborhood of hotels nestled among residential homes and locally owned antique stores and art galleries.

Islamorada is a family-friendly key and the Islander Resort offers all the amenities: a children’s pool, an adult-only pool, hot tubs, a pool-side bar, a beach fronted by calm waters, a dock, and a wide selection of activities and watersports. Each room has been recently renovated so that the high ceilings and private porches offer a cool respite from the hot weather. A cool feature that makes the hotel stand out is the fact that all the buildings are covered by solar panels.