Key West's more mellow than Miami, but it's definitely no convent, a fact made more than clear at the Bourbon Street Complex, a network of gay bars and clubs on Key West's main drag, Duval Street. The titular bar, Bourbon St. Pub, offers the good old fashioned dance music and go-go boys one would expect from a gay watering hole, but outdoors, at New Orleans Guest House, you'll come upon a clothing optional poolside garden bar that's pure Key West. It's around these parts that the Conch Republic's gays and their admirers ring in the new year in grand fashion, as seen above.
Diagonally across the street there's 801 Cabaret, where in addition to strong drinks you can play bingo, sing your heart out during karaoke and, yes, sit back for cabaret acts. Those in the mood for a rougher evening will be delighted to find Key West's leather and Levi's bar, 1 Saloon, right next door.
If you can pull yourself away from Bourbon St's revelry and are down to dance, check out Aqua, the biggest, gayest dance spot in town. Bonus: it also features drag shows every night of the week. And if you want even more drag revues, tucked at the further end of Duval is the Crystal Room at the La Te Da Hotel.
Ladies looking for a different sort of woman, meanwhile, will find them at Pearl's Patio, Key West's premier lesbian bar.
In the mood for a dive away from Duval's touristy vibe? Head over to Bobby's Monkey Bar on Simonton Street, where the friendly staff mix formidable drinks and friendly locals are typically down to play some pool. Be sure to swing by for karaoke Thursdays. And if for some reason you have free time in the afternoon, check out the tea dances at Atlantic Shores Resort.
While most of the hotels and resorts have bars, the taproom at Speakeasy Inn stands out. Though not gay, they're definitely welcoming, and the locals who saddle up to the Inn's bar can give great oral history. And if you take your cocktails seriously,
clean yourself up and have a sophisticated sip at Orchid Bar.
Live music can be found at the Green Parrot on Whitehead Street. Or, if you're curious to see what has been described as "the wildest and wackiest country bar," mosey on to Cowboy Bill's Honky Tonk Saloon. The topless women running around should be indication enough, but just to be clear, this is a straight bar. Still, like most of Key West, it's more than open to hosting LGBT patrons, as is the divey The Bull and its terraced cousin sibling upstairs, Whistle Bar.