Where to Stay and Play in Key West

OUT sent newlyweds Kit Williamson and John Halbach, from the acclaimed series, Eastsiders, to our favorite gay mecca, Key West. From breakfast pineapple pancakes to poolside margaritas, and from private tours of the Hemingway Home to nude snorkeling off the Florida coast, these guys experienced and discovered all that Gay Key West has to offer. Follow along as Kit and John take you OUT in Key West. 

Key West is a great tourist destination for the LGBT community, and they have the bars and hotel accommodations to prove it. No matter what kind of scene you’re looking for, you’ll be able to find it here. 

The Island House

All-male and clothing optional, The Island House has everything you need under one roof. In addition to great rooms and suites, guests have access to a swimming pool, multiple hot tubs, a restaurant, and a gym. 

Kit’s Take: The Island House definitely has a more festive vibe, with a weekly clothing optional pool party, and the pool and cafe bar are both open 24/7. That said, you can definitely unwind and relax here as well. We recommend booking one of their detached apartment suites if you’re looking for a more low-key, private getaway. 

Alexander’s Guest House

Alexander’s Guest House welcomes both members of the LGBT community, and allies. Simultaneously stylish and homey, this three story Conch style home is listed on the National Historic Register. Guests are treated to breakfast, a jacuzzi, a swimming pool, and a complimentary happy hour to mix and mingle with new friends. 

Kit’s Take: Alexander’s Guest House is absolutely beautiful and we had an amazing time at their happy hour chatting with the guests gathered around the pool and over complimentary margaritas. The atmosphere was really warm and welcoming; all the guests and staff were so friendly. We’d definitely love to go back and enjoy the sunset in one of their hammocks again. 

The Cabaret at LeTeDa

Featuring both a piano bar and a cabaret space, The Cabaret at LeTeDa is home to some of the best shows in Key West seven days a week. Check out Christopher Peterson’s Eyecons or Randy Roberts Live! to see incredible celebrity impersonators, or let 3sum treat you to the greatest hits of Motown, Disco, and today in the piano bar. 

Kit’s Take: Come for the Marilyn Monroe opening number and stay for the Judy Garland/Liza Minelli finale. Christopher Peterson puts on a great show! We recommend grabbing dinner at the cafe at LaTeDa before or after. 

Aqua Bar and Nightclub

Offering afternoon happy hour, nightly shows, and Karaoke Monday-Thursday, Aqua is always one of the busiest bars in the gayborhood. 

Kit’s Take: These southern queens know how to put on a great show; just sit back and let them show you how it’s done! And bring singles!

Bourbon Street Pub

Key’s West’s original and only video bar, Bourbon Street Pub has something for everyone with nightly performances from the famous “Men of Bourbon” gogo dancers, VJ’s, live shows, 5 separate bars, and a male only clothing optional bar with pool and jacuzzi in the back. If you want to make some extra cash while you’re in town, Joe the owner is accepting shirtless pics for consideration for future “Men of Bourbon.”

Kit’s Take: This place brings a lot of the fun of the big easy down to Key West.  Growing up down south, I had my first kiss at the Bourbon Street Pub in New Orleans and I felt like this bar captured a similar vibe to its Louisiana counterpart.

​For more coverage of Kit and John's trip to Key West, head to OUT.com/gay-key-west, and to book your own OUT in Key West experience, visit Fla-Keys.com.