Before 2018, Key West never appeared on my travel radar. It looked pretty, comfortably gay-friendly and maybe even a bit kitschy, in a Daddy’s Girls kind of tropical veranda. I was expecting a laid back Florida “flip flops and flip cup” vibe. I expected to eat key lime pie, float around in a Speedo, and watch those six-toed cats at the Hemingway house.
What I didn’t expect was to fall in love with the island.
With increasingly harsh winters beating New York every year, it doesn’t take much to make this city more stylish elsewhere in 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 present an increased level of complication.
Ease of entry is always a plus for any gay traveler, but Key West offers the complete tropical fantasy as soon as you step onto the tarmac at its charming little airport. (Don’t worry, there’s still a bar.) Warm breezes, sunshine, and palm trees seem much closer to heaven than begging.
The island has a host of beaches, from the soft sands of Smathers to the local favorite at Fort Zachary Taylor, but once you catch a glimpse of the clear waters, it’s hard to resist. Options on the water range from gentle 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 child like me could appreciate Key West’s ideal climate, although I personally prefer my vitamin D with a vodka chaser. A cocktail by the pool is always worth the price of airfare, in my opinion, and there are plenty of options for sipping and soaking in Key West, especially for gay travelers.
There are four primarily LGBTQ+ guesthouses on the island, including three clothing-optional catering specifically for men. For many travelers, the culture of clothing optional is the primary motivation for visiting. This is uncharted territory for people like me, for whom dressing comfortably usually involves at least a cardigan. I learned that it’s not only possible to go from swimming in a shirt to leaving everything hanging out to happy hour, but the confidence and comfort it inspired became my fondest memory of my time in Key. West.
Don’t get me wrong, there’s no shortage of things to do while wearing clothes in Key West either. There are excellent restaurants that combine the creativity and imagination of the island with the unique culinary culture and local seafood. Yes, there is the famous lime pie, but there are staples like conch, crawfish and hogfish.
Nightlife can still be naughty at Island House after dark, bumping and rubbing alongside go-go boys at Bourbon Street Pub or late night at Saloon 1. dirty girls at 801 Bourbon Bar, run by the iconic Sushi. Down the street at LaTeDa, celebrity impersonators extraordinaire Christopher Peterson and Randy Roberts wow audiences several nights a week.
However, dipping your toe into the island’s clothing-optional culture unlocks most of visiting Key West (and we don’t just mean eye candy).
Naked happy hours and pool parties are a society staple in Key West. You can see people dancing in the pool at the bar behind Bourbon Street and the New Orleans House guesthouse while partying tourists on Duval Street mingle with laid-back locals over drinks. At the legendary Island House, Wednesday and Sunday pool parties are lively with heavy pours, raffle prizes, and enough naked men of all shapes and sizes to satisfy almost any taste. The gay-owned and operated BluQ offers a men-only, no-clothes sail and snorkel for those looking for the funniest sunburn you’ve ever had.
If this all sounds a little 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 that straight travelers tend to spread. The rebel streak is steeped in the island’s history, as a haven for pirates, artists, and just plain weirdos. A long line of creators 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 muse of John Waters Divine, beloved children’s book author Judy Blume and even Superior gun Star Kelly McGillis is one of the icons who have lived on the island. Perhaps most notably, this is evident in Key West’s ironic cessation of the United States in the 1980s.
As a proud pirate/artist/weirdo myself, this is what I enjoy most about the visit. The unique mix of LGBTQ+ travelers and locals means there’s never a shortage of interesting conversations over a cocktail or a conch fritter. An open mind is all it takes, as the friendly locals encourage 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 styles. It could be a restorative solo respite, a really crazy boys weekend, a romantic getaway, or countless other combinations.
With the right attitude, you will be rewarded not only with an unforgettable vacation, but also with a host of new friends. (And I’m not just talking about the ones you meet in the hot tub or the steam room.) It’s been the biggest reward for my time talking with local comedians, writers, drag queens, and even the mayor. Teri Johnston (the first openly- gay woman elected mayor of Florida). It’s a special place that attracts a special type of person.
It’s always nice to find your loved ones, but nothing beats doing it in paradise.