It’s not hard to sell prospective gay travelers on Key West’s gorgeous weather and vibrant LGBTQ+ community, but when it comes to the island’s clothing-optional culture, many folks are quick to decide it’s not for them.
I should know. I used to be one of those people.
I’d never been even a little curious about a clothing-optional vacation (in fact, I was fully swimming with a shirt on well into my 30s), but when I arrived for my first ever visit to Key West, it was nothing like I imagined … or feared.
If you’ve ever been curious about what it’s like to trade your swimsuit for your birthday suit, we’ve got 10 reasons why Key West is the perfect place to give clothing-optional a try on your next vacation.
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1. You’re In Control
The most important thing for first-timers to keep in mind is that “clothing-optional” does not mean “nudity-mandatory.” In most Key West clothing-optional spaces, you’ll encounter folks in all states of undress. Sure, some folks are wearing their bathing suit in the pool. They’re typically the minority, but they’re no less welcome.
“Just remember, it’s optional,” said Anthony Sibilly-Juarez, general manager of the Equator Resort, one of Key West’s clothing optional guesthouses. “The clothing-optional aspect is not something that is required. It’s not what you’re fearing it is. You’re going to have a good time, you’re going to relax. If you choose to lose your clothes, great, if you don’t, great, too.”
Is it a sexually-charged atmosphere? Sure. But not much more than most gay spaces. No matter anyone’s motivations, there’s room for all comers.
“It becomes a sanctuary where you feel safe, you are among like-minded people,” Sibilly-Juarez said. “Whether you’re more of a nudist, and you enjoy the freedom of it, or the more sexual component to it, there’s lots of factors that play into it.”
2. You’ll Fit Right in
A major concern for a lot of guys considering a clothing-optional vacation is what everyone else there will look like. Of course, every trip will feature its own rotating cast of fellow travelers, but it’s fair to expect you will be surrounded by people whom you do and do not want to have sex with, as well as people who do and do not want to have sex with you. Sort of like anywhere else.
On my trips to the island, I’ve met men ages 18-80, hairy and smooth, twinks, bears, otters and every zoo creature in between. If there’s one kind of person not welcome in the Key West “One Human Family,” it’s the judgmental.
3. You Can Let Loose
Most visitors aren’t in Key West for a long time, but they are typically there for a good time, which makes it easy to let your guard — and swim trunks — down.
“During one of my first conferences, someone asked me, “What do you do for a living?” Sibilly-Juarez said. “Well, I make sure the boys are naked, the porn is on and the liquor is flowing.”
Who could ask for anything more?
Because Key West is such a popular vacation destination, folks are already primed to party. It’s easy to strike up a conversation with a good-natured stranger when everyone’s leaving their worries (and clothes and inhibitions) at the door.
4. You May Surprise Yourself
Just slipping out of your Speedo may be achievement enough, but that could just be the beginning.
Sibilly-Juarez recalled one specific guest:
“I had one guy that came here, he was older, in his 60s or so, and he just came out of the closet, divorced his wife, has kids that are grown adults. He was in the military. He literally said. ‘I don’t know how to be gay.’ This was a sanctuary for him. By the time he left, he blossomed into a blooming flower.”
5. You’ve Got Options
Not all clothing-optional experiences are alike, and even on the 2-by-4 mile island, three male-only, clothing-optional guesthouses offer visitors a variety of vibes.
Equator, for example, boasts a collection of uniquely designed rooms, pools and jacuzzis in a sexy, secluded, grotto-like atmosphere. Every room has its own bathroom (versus guesthouses that offer a broader price range with shared bathrooms), and they don’t offer memberships from locals. It keeps the property peaceful and serene, though happy hour brings out guests to mix and mingle.
Meanwhile, New Orleans House on Duval Street offers guests unparalleled access to Key West nightlife and the backyard bar scene at Bourbon Street Pub. Centrally-located near the gay bars and drag shows, it’s a great spot for the guest who loves the nightlife (and doesn’t mean a little extra late-night ambiance from the streets below).
Then there’s Island House, which famously blends the best of bathhouses and resort amenities while attracting a steady stream of locals for a reliably lively party atmosphere. The dedicated “play space,” steamrooms and wild pool parties make it a more sex-forward environment.
6. You Don’t Need Apps to Get Laid
Let’s get real: For all the talk about how sex isn’t a necessary component of the clothing-optional experience, it’s certainly not hard to find either.
“This is debauchery at its finest, but it’s five-star sleaze,” said Jeffrey Smead, general manager of Island House.
At Island House, sex does spill over from the “red room” to the jacuzzi and steam rooms, but it’s just as easy to avoid if it’s not your thing. For those travelers who have replaced cruising with apps, Island House offers a radically refreshing way to connect.
“For that new generation that isn’t used to hearing about a product like this, they kind of put it in a box, they say, ‘Oh, well, that’s a bathhouse, and I don’t go to bathhouses.’ It’s like why don’t you just take the label away, and give yourself permission to experience something new?”
7. You’ll Make Friends
No, really. Not “friends” like the guy saved in your phone as “Brandon? (Eagle),” but actual friends.
“No other environment introduces people so casually yet in a setting that is so outrageous,” Smead is quick to point out. “This is the place where the couple from Tulsa, Oklahoma meets the couple from Tampa meets the couple from Connecticut, and they end up going to dinner together on the fly. Then a couple of them end up going to Bourbon Street Pub for late night cocktails and then they inevitably will come back 3 a.m. to Island House and get some elevated bar fare here, then hot tub and jacuzzi time. That’s what this place does, you don’t plan your experience. You come here with a clean slate, you take your watch off your wrist, you put your cell phone down and you jump in headfirst into the experience.”
I’ve seen this at work in my own travels around the island. In just three short trips, I’ve nurtured enough relationships with locals and fellow travelers to coordinate future travel together. It may not have been solely the nudity that led to our friendship, but the general sense of openness and community didn’t hurt.
8. You’ll Take More Than Half Off at This Sail
Clothing-optional Key West experiences aren’t limited to the guesthouses — or even dry land! The BluQ offers all-male, clothing-optional sails (as well as sunset sails open to all LGBTQ+ people).
The trip includes a half day on Key West’s beautiful waters, snorkeling, enjoying drinks (the sails are BYOB) on a sandbar with a group of fellow travelers. Sure, sitting in the surf with a cold one is great, but you should try it while soaking up all the sun in those places it doesn’t usually shine.
Group sizes range from less than 10 to about two dozen for larger groups. It’s a great way to meet travelers staying at different guesthouses.
9. You Can Experience a True Key West Party
For those looking for an even deeper dive into the clothing-optional experience, there’s Bone Island Bare It All, a gathering of gay nudists that takes over all three, all-male, clothing-optional resorts, plus Alexander Guesthouse, which typically is open to LGBTQ+ guests of all genders.
10. You’ll See How Normal Naked Can Be
The most surprising thing about the nudity in Key West is just how unsurprising it can feel in practice. In Key West, even the realtors are naked, just ask Paul Brooks.
You might recognize him from his cheeky postcards displayed at Island House and Equator (and soon New Orleans House as well). On the front, he’s naked, a black bar with the text “LOOKING … ” covering all the best bits. On the back it says, “TO BUY OR SELL A HOME IN KEY WEST?” It’s a clever way to catch some eyeballs, but it’s also a tactic tailor made for the Key West crowd.
“Being here, being in a very clothing-optional community definitely allows me to do that,” he said. “Otherwise, it would be very plain real estate marketing.”
Key West’s queer community and welcoming “Come As You Are” spirit are two reasons it’s so open to clothing-optional experiences, but Brooks thinks there’s another element at play.
“It’s the tropics,” he said. “You’re in endless sunshine, of course you want to get naked and sunbathe, who doesn’t?!”
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