Day or Night, Key West Entertainment Abounds

Key West’s wide array of entertainment — throughout the night, into the wee hours and all day, every day — means it’s challenging to experience all there is to do. LGBTQ visitors can enjoy theater and music performances, book on-the-water excursions, meet new friends for dining or drinks, attend a drag show or simply “chillax” in the subtropical surroundings.
While Key West’s laid-back attitude means everyone is welcome virtually everywhere on the 2-by-4-mile island, some entertainment offerings are designed to appeal primarily to LGBTQ visitors.
Popular activities include happy hours, afternoon tea dances, adult pool parties, spirited karaoke and delightfully outrageous drag shows. LGBTQ 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 and 800 blocks of Duval Street, the town’s main 14-block entertainment and shopping thoroughfare that stretches from the Atlantic Ocean to the Gulf of Mexico.
Among the most popular spots are the Aquaplex at 711 Duval St., where “Reality is a Drag” showcases drag performers and DJ dance music. The compound’s entertaining attractions include karaoke, burlesque shows, a complimentary pool, outdoor and indoor dining and imbibing and dancing. The Sidebar dance club connects the Aquaplex’s five on-site venues.
Bourbon St. Pub, 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 extensive happy hours, afternoon karaoke on weekends, and drag performances by the fabulously bedecked Sushi and the 801 Girls.
La Te Da, at 1125 Duval St., is a popular boutique hotel whose upstairs Crystal Room features performers Randy Roberts and Christopher Peterson, nationally regarded as leading female impersonators. La Te Da also offers an acclaimed restaurant and popular 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 located at the southernmost tip of the continental United States. Venues 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 on the campus of the College of the Florida Keys. 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, just off Duval Street, offers contemporary films and independent foreign cinema.
Because of Key West’s year-round subtropical climate, daytime entertainment typically focuses on swimming, sunning and watersports. Visitors might choose to relax poolside or explore the beach at Fort Zachary Taylor Historic State Park or Higgs Beach.
For those preferring 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 charters 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 below the horizon.
Daytime visitors can cool off by exploring Key West’s many museums and nature attractions. Among them are the Key West Butterfly & Nature Conservatory at 1316 Duval St., Ernest Hemingway Home & Museum at 907 Whitehead St., Mel Fisher Maritime Museum at 200 Greene St. and Tennessee Williams Museum at 513 Truman Ave.
The island’s most popular photo stop is the Southernmost Point, a larger-than-life buoy that marks the southernmost spot in the continental United States — only 90 miles from Cuba. Virtually every visitor to Key West goes there for a selfie or group photo.
Most also experience the nightly Sunset Celebration, featuring colorful street performers and an island-style outdoor market. People of all ages flock to Mallory Square, the historic pier overlooking Key West Harbor and the Gulf of Mexico, to enjoy the carnival-like atmosphere as the sun sinks in orange-red splendor.
Key West visitor information: or 1-800-LAST-KEY
Gay Key West Visitor Center:, 305-294-4603 or 1-800-535-7797
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