Don't come to Key West expecting world-class nightlife. The options are limited, and can't even begin to compare with Miami or even Fort Lauderdale in terms of size, sophistication or energy. This is decidedly a low-key town -- except during Fantasy Fest and WomenFest each fall. However, the addition of adult licensing for all the bars means you can expect the full monty from the local male dancers.
The biggest dance spot is Aqua (711 Duval St.; 305/294-0555), which hosts a daily happy hour, drag shows five days a week and live entertainment Sundays. KWest Men (711 Duval St.; 305/292-8500) is a strip bar next door.
Even if drag shows make you roll your eyes, don't miss the stars of La Te Da's Crystal Room Cabaret (1125 Duval St.; 305/296-6706). Performers Randy Roberts and Christopher Peterson present top-notch celebrity impersonations and actually sing. Peterson even ups the ante by completing his character transformations in full view of the audience. "Broadway 3 Ways," which pairs a gay boy with two drag queens, rounds out the lineup.
The gay epicenter of Duval Street is the Bourbon Street Complex (724-801 Duval St.), which includes multiple bars, a gay guesthouse, and restaurants. 801 (801 Duval St.; 305/294-4737), a streetfront cruise bar, packs in a straight and gay mix for its nightly second-floor drag shows. The 801 also encompasses The One Saloon, a leather/Levi bar which is accessible to the rear. Bourbon Street Pub (724 Duval St.; 305/296-1992) is diagonally across the street and remains the most popular nightlife option. A friendly mix of ages and tastes congregates around the large central bar, where attractive strippers vie for the attention of dollar-toting tourists. Adjacent to (and accessed via) the Bourbon Street bar is the very popular New Orleans Guesthouse poolside bar, where clothing-optional swimming and sunbathing is welcome and a fun, boozy crowd plays. The pool patio area has recently been expanded. Women are welcome at the poolside bar after 6 p.m.
Head around the corner to the newest member of the complex, Bootleggers (411 Petronia St.), a country & western dance bar. For T-dance on Sunday afternoons, head to the Atlantic Shores Resort. T-Dance officially starts at 8 p.m., but most revelers don't arrive until well past 9 p.m. The pier, bathed in moonlight, provides a romantic setting above the warm Atlantic water. The divey Bobby's Monkey Bar (900 Simonton St.; 305/294-2655) caters to a mixed local crowd, which gathers late at night.
Pearl's Patio, a shaded bar and caf?, provides the only nightlife option just for women on the island, and happy hour usually draws a lively crowd. Games night and karaoke are the draw on Saturdays, movies are shown on Wednesdays and TV shows, such as The L Word lure in local ladies and visitors on Mondays and Thursdays.