Before 2018, Key West never appeared on my travel radar. It seemed pretty, comfortably gay-friendly and maybe even a little kitschy, in a Golden Girls tropical lanai sort of way. I expected a relaxed, “flip-flops and flip cup” Florida vibe. I expected to eat key lime pie, float around in a Speedo and check out those six-toed cats at the Hemingway house.
What I didn't expect was to fall in love with the island.
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. Leaving dirty snowbanks for sand and surf is a no-brainer. However, especially in today's increasingly complex travel environment, even nearby international destinations like Mexico have a heightened level of complication.
Ease 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. (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.
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. 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.
Even a perpetual indoor kid like myself could appreciate Key West's ideal climate, though I prefer my Vitamin-D with a vodka chaser, personally. 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.
There are four primarily LGBTQ+ guesthouses on the island, including three clothing-optional catering specifically to men. For many travelers, the clothing-optional culture is the primary motivation for visiting. It's unfamiliar territory for folks like myself, for whom dressing comfortably typically involves at least one cardigan. 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.
Make no mistake, there's no lack of things to do while wearing clothes in Key West, either. There are excellent restaurants that blend the creativity and imagination of the island with the unique culinary culture and locally-sourced seafood. Yes, there's the famous key lime pie, but there are staples like conch, spiny lobster and hogfish.
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. 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. Down the street at LaTeDa, celebrity impersonator extraordinaires Christopher Peterson and Randy Roberts wow audiences several nights a week.
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).
Naked happy hours and pool parties are social staples in Key West. 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. 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. 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.
If it all sounds a bit radical, that's because it is. 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. The rebellious streak is baked into the island's history, as a haven for pirates, artists and just plain weirdos. A long line of creatives have called the island home, including Ernest Hemingway, whose house is still a favorite point of interest for visitors, and Tennessee Williams, whose career can be celebrated at the small, but well-curated Tennessee Williams Museum. Original West Side Story scribe Leonard Bernstein, drag legend and John Waters muse Divine, beloved children's book author Judy Blume and even Top Gun star Kelly McGillis are among the icons who have lived on the island. Perhaps most notably, it's evident in Key West's tongue-in-cheek cessation from the United States in the 1980s.
As a proud pirate/artist/weirdo myself, it's what I appreciate most about visiting. The unique mix of LGBTQ+ travelers and locals means there's never a shortage of interesting conversation to be found over a cocktail or conch fritter. An open-mind is all that's required, as the friendly local populace encourages to “come as you are ” … as long as who you are isn't a judgmental jerk.
The welcoming atmosphere means Key West caters to a wide variety of travel style. It can be a restorative solo respite, a truly balls-out boys weekend, a romantic getaway or countless other combinations.
With the right attitude, you'll be rewarded with not only an unforgettable vacation, but a slew of new friends. (And I'm not just talking about the ones you meet in the hot tub or steam room.) It's been the greatest reward from my time spent speaking with local comedians, writers, drag queens and even Mayor Teri Johnston (the first openly-gay woman elected mayor in Florida). It's a special place that attracts a special kind of person.
It's always nice to find your people, but nothing beats doing it in paradise.