Key West’s wide array of entertainment — throughout the night, into the wee hours and all day, every day — means it’s a real challenge to experience everything there is to do. LGBT visitors can enjoy theater and music performances, book on-the-water excursions, meet new friends for dining or drinks, attend a drag show, simply “chillax” in the subtropical surroundings and much more.
Key West visitors can enjoy lazy afternoons by the pool at renowned guesthouses like New Orleans House. (Photo by Mike Freas, Florida Keys News Bureau)
While the 2-by-4-mile island’s laid-back attitude means everyone is welcome virtually everywhere, some entertainment offerings are designed to appeal primarily to LGBT visitors.
Popular activities include happy hours, afternoon tea dances, adult bingo or Texas Hold ‘Em games, spirited karaoke, and delightfully outrageous drag shows. LGBT and straight visitors and residents mingle freely at “come as you are” establishments throughout the island.
Some are located in the “Pink Triangle” around the 700 block of Duval Street, the town’s main 14-block entertainment and shopping thoroughfare — which stretches from the Atlantic Ocean to the Gulf of Mexico.
Among the most popular spots are Aqua, at 711 Duval St., where “Reality is a Drag” showcases the performers Inga and the Aquanettes. Other attractions include karaoke, poker, intriguing special events, and Aqua’s new “Sidebar” dance club.
Bourbon St. Pub, at 724 Duval St., is known for its witty themed parties, male dancers and other performers, and a male-only clothing-optional garden bar and pool. Diagonally across the street at 801 Duval St. stands the 801 Bar, boasting an extensive happy hour and bingo on Sunday afternoon, karaoke nights and drag performances by the fabulously bedecked Sushi and the 801 Girls.
La Te Da’s Terrace Bar offers a warm welcome and great people-watching on famed Duval Street. (Photo courtesy of La Te Da)
La Te Da, at 1125 Duval St., is a popular boutique hotel whose upstairs Crystal Room showcases performers Randy Roberts and Christopher Peterson, regarded nationally as leading female impersonators. La Te Da also offers an acclaimed restaurant and Sunday afternoon tea dances.
Other favorite spots include Bobby’s Monkey Bar, located off the beaten path at 900 Simonton St., frequented by locals for its friendly nightly karaoke and reasonably priced drinks.
Key West’s top-notch theater, featuring big-city sophistication and professionally trained entertainers, may seem surprising for a destination at the southernmost tip of the continental United States. Establishments offer theatrical and musical shows and performances, hosting guest artists and road companies from around the world.
Theaters and musical venues include the Waterfront Playhouse, Red Barn Theatre, San Carlos Institute, Key West Theater and Tennessee Williams Theatre at Florida Keys Community College. Named to honor the Pulitzer Prize–winning playwright who lived in Key West for decades, the spacious playhouse hosted the premiere of Williams’ “Will Mr. Merriweather Return From Memphis?”
For fans of the silver screen, Tropic Cinema offers contemporary films and independent foreign cinema just off Duval Street.
Few dining options can top an open-air feast overlooking the Atlantic Ocean in easygoing, subtropical Key West. (Photo by Mike Freas, Florida Keys News Bureau)
Because of Key West’s year-round subtropical climate, daytime entertainment typically focuses around swimming, sunning and watersports. Visitors might choose to relax poolside or explore the beach at Fort Zachary Taylor Historic State Park (sometimes nicknamed Fort Elizabeth Taylor) or Higgs Beach near the Reynolds Street pier.
If you prefer livelier activities, the azure water surrounding Key West is the place to be. The only living coral barrier reef in the continental United States can be found just 7 miles offshore, teeming with vivid tropical fish and fantastic coral formations that draw divers and snorkelers. Snorkel and scuba excursions are plentiful, with instruction available for novices. Paddleboarding and kayaking are popular as well.
Several vessels offer specifically gay trips and even clothing-optional excursions. And no escape to Key West would be complete without taking a romantic sunset cruise — listening to the creak of the rigging as the tropical sun descends beneath the horizon in a blaze of vivid orange and pink.
Ready to plan a Key West getaway to sample the island’s entertainment options? Begin here!
Click here to subscribe to the Florida Keys & Key West’s LGBT travel blog.
