The rebellious streak is baked into the island’s history, as a haven for pirates, artists and just plain weirdos. There’s a well-established transgressive side to the island belied by the tacky t-shirt shops and tourist traps straight travelers tend to spread. If it all sounds a bit radical, that’s because it is. The gay owned and operated BluQ offers a men-only, clothing-optional sail and snorkel for those seeking the most fun sunburn you’ve ever had. At the legendary Island House, Wednesday and Sunday pool parties are lively affairs with heavy pours, raffle prizes and enough naked men of every shape and size to satisfy almost anybody’s tastes. You may catch some folks bobbing in the pool at the bar behind Bourbon Street and New Orleans House guesthouse while tourists partying down Duval Street mix with laidback locals over drinks. Naked happy hours and pool parties are social staples in Key West. Though, dipping your toe into the island’s clothing-optional culture unlocks the greatest part about visiting Key West (and we don’t just mean for the eye-candy). Down the street at LaTeDa, celebrity impersonator extraordinaires Christopher Peterson and Randy Roberts wow audiences several nights a week. There’s drag aplenty on Duval, from the crowd-pleasing lip syncs at Aqua to the down and dirty gals at 801 Bourbon Bar, led by the iconic Sushi. Nightlife can still be naughty at Island House after dark, bumping and grinding alongside the go-go boys at Bourbon Street Pub or late nights at Saloon 1. Yes, there’s the famous key lime pie, but there are staples like conch, spiny lobster and hogfish. There are excellent restaurants that blend the creativity and imagination of the island with the unique culinary culture and locally-sourced seafood. Make no mistake, there’s no lack of things to do while wearing clothes in Key West, either. I learned it’s not only possible to go from swimming with a shirt on to letting it all hang out at happy hour, but the confidence and comfort it inspired became my greatest souvenir from my time in Key West. It’s unfamiliar territory for folks like myself, for whom dressing comfortably typically involves at least one cardigan. For many travelers, the clothing-optional culture is the primary motivation for visiting. There are four primarily LGBTQ+ guesthouses on the island, including three clothing-optional catering specifically to men. Key West’s Island House serves up a popular pool party twice a week. A poolside cocktail is always worth the airfare, in my opinion, and there are lots of options to sip and soak in Key West, especially for gay travelers. Options on the water range from mild to wild, from leisurely sunset cruises to jet skis and parasailing, but no trip to Key West is complete without leaving dry land at least once.Įven a perpetual indoor kid like myself could appreciate Key West’s ideal climate, though I prefer my Vitamin-D with a vodka chaser, personally. The island has a host of beaches, from the soft sands of Smathers to the local favorite at Fort Zachary Taylor, but once you get a glimpse of the clear waters, they’re tough to resist.
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A beautiful view of Smathers Beach in Key West. (Don’t worry, there’s still a bar.) The warm breeze, the sunshine and the palm trees feel much closer to paradise than the panhandle.
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However, especially in today’s increasingly complex travel environment, even nearby international destinations like Mexico have a heightened level of complication.Įase of entry is always a plus for any gay traveler, but Key West delivers the full tropical fantasy the moment you exit onto the tarmac at its small, charming airport. Leaving dirty snowbanks for sand and surf is a no-brainer. With increasingly brutal winters descending on New York City each year, it doesn’t take much to get this city slicker anywhere else come February. What I didn’t expect was to fall in love with the island. I expected to eat key lime pie, float around in a Speedo and check out those six-toed cats at the Hemingway house. I expected a relaxed, “flip-flops and flip cup” Florida vibe. It seemed pretty, comfortably gay-friendly and maybe even a little kitschy, in a Golden Girls tropical lanai sort of way.
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Photo by Mike Freas/Florida Keys News Bureauīefore 2018, Key West never appeared on my travel radar. Key West’s iconic Southernmost Point marker is a popular spot for a photo.