Travelers love Key West for the sunshine, and there’s plenty of it. But when the sun sets, this welcoming destination transforms into something entirely different, with a dynamic nightlife scene, craft cocktails, al fresco dining, and unique experiences that can only be found at the southernmost tip of the continental United States.
Drag legend Randy Roberts, who first visited Key West in 1986 and relocated permanently to the area 12 years later, says, “It was magical” to see so many local businesses thriving. At only four miles long and two miles wide, Roberts, like many locals and visitors alike, finds getting around town easy and hasn’t left. As he puts it, “You can’t beat the weather.”
GayCities discovered some terrific finds, including dancing, entertainment, drag — and even a graveyard tour — all adding to the perfect 48 hours in Key West (or longer!).
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The best drag shows in Key West
Despite its compact size, Key West is packed with entertainment options, and some of the country’s premiere drag entertainers have chosen to join Roberts in calling Key West home. Roberts plays La Te Da’s intimate cabaret venue, the Crystal Room, bringing to life some of our favorite entertainers, including Cher, Bette Midler, and Barbra Streisand.
Christopher Peterson headlines the venue on alternate days for those hoping to catch a glimpse of Lady Gaga, Madonna, and other pop icons and celebrities. For those looking for a quick show tune, the piano bar offers entertainment nightly with no cover charge.
The Aquaplex, a longtime anchor of Key West nightlife, serves up nightly drag shows with a rotating roster of queens. And if you’re traveling with a group, VIP booths for up to six people ensure extra-special attention. Located at the intersection of Duval and Angela Streets, the recently renovated venue now boasts four unique spaces, an expanded dance floor, and new lighting and sound all under one roof.
“By upgrading our patrons’ experience in a variety of new and enhanced venues, we will continue to provide the finest entertainment complex in the Keys,” says owner and general manager Michael Ingram, who purchased the club in 2013.
Of course, you can’t live on drag alone (or can you?). The Aquaplex features Poké in the Rear, which serves lunch and dinner, along with several other venues for cocktails and dancing, including an expanded dance floor and CLUB 504 at the Sidebar, an outdoor garden bar, and 22&CO, famous for its neon flamingo design.
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A ghostly good time
Key West is known as one of the most haunted cities in America and was originally called “Island of Bones.” Nearly a dozen different tours offer access to the creepy and captivating stories of Key West, including the Ghosts & Gravestones Tour.
Board the Trolly of the Doomed and hear intriguing stories about Captain Tony’s Saloon, Elvira’s grave, and a visit to Key West Shipwreck Treasure Museum. And if you thought M3GAN was terrifying, wait until you encounter Robert the Doll. After decades of frightening incidents, the doll is now glass-encased at the East Martello Museum, though his evil gaze has been known to send chills down the spines of even the most fearless visitors.
For hands-on ghosthunting, paranormal pioneer David Sloan’s Ghost Key West tour outfits participants with ghost-hunting equipment, including electromagnetic field detectors and custom-built spirit boxes for an other-worldly experience.
A taste of Key West
Key West’s culinary and craft cocktail scene continues to explode. With access to some of the freshest seafood on our eastern shores, chefs take advantage of local ingredients while mixologists reimagine the classics in inventive ways.
Self-described as “one part retro supper club, one part sassy bistro, and one part highly personal whim,” The Flaming Bouy embodies the very best of quintessential Key West. Diners will discover a bounty of local seafood, including pink shrimp, yellowtail snapper, and black grouper, accompanied by an affordable wine list.
For more than 40 years, Mangoes has brought Caribbean flair to Key West with a menu that pays homage to Bahamian, Cuban, and West Indies culture. Blackened cobia and jerk-style chicken with spicy sweet potatoes are among the menu’s highlights, with cocktails to match, like a spicy Mexican mule and habañero Bloody Mary. Live entertainment is always on hand to keep things bustling. And for those who prefer day drag, its monthly Drunken Drag Brunch benefits local charity partners, including Reef Relief, MARC House (which supports developmentally and intellectually disabled adults), and the Key West Business Guild.
Where to stay in style in Key West
Key West has plenty of accommodation options for every type of traveler. Here are some noteworthy options to consider:
Grand Maloney — The recently opened LGBTQ+-friendly property dates back to the 19th century and features chic, historic touches with modern amenities. With only six rooms, it’s ideal for an exclusive takeover. An outdoor pool and patio, second-floor balcony, and lobby offer plenty of nooks to hang out with friends or curl up with a good book or musical recording by one of Key West’s LGBTQ+ cultural icons, like Tennessee Williams or Jerry Herman.
Alexander’s Guesthouse — The gay-owned and operated guesthouse consists of three historic homes built between 1902 and 1904. Architectural details create Instagram-worthy moments throughout the property, while three levels of sun decks provide the ideal backdrop for that perfect Key West weather.
The Capitana Key West — Opened in 2020, this boutique property offers the intimacy of a bed & breakfast with the amenities of a luxury hotel, including beachside cabanas, spacious cottages, and a pet-friendly policy to travel with your favorite pup.
Whether by day or night, Key West continues to attract LGBTQ+ travelers worldwide. And if you’re looking to meet more of them, consider visiting for one of the city’s landmark events, including Key West Pride (June 7-11) or Womenfest (September 6-10).
