Island House RAW: What’s It Really Like at Key West’s Clothing-Optional, All-Male Resort?

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Island House RAW: What’s It Really Like at Key West’s Clothing-Optional, All-Male Resort?

You’ve seen the sexy ads, watched the slickly-produced videos and heard all the wink, wink coy dispatches from Key West’s all-male, clothing optional resort, Island House. But what’s it really like at the Key West institution that prides itself on being the “Best Gay Resort In the World?”

The first thing you must understand about Island House is that it could only really exist in a place like Key West, where the vibrant LGBTQ community is firmly established and the island’s welcome “come as you are” attitude all but requires visitors to drop any semblance of pretense … and, well, clothing. There are a few clothing-optional guesthouses (or with clothing-optional areas), but there are also bars with clothing-optional yards and street festivals where skin is in, and the style is letting it all hang out.

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The phrase clothing-optional isn’t the sort of thing you see on your typical, cheesy Caribbean all-inclusive brochure, so, naturally, people have questions. Is it just sex everywhere all the time? Do I have to be naked? Will I be the only one who doesn’t look like an Instagram influencer? (Or, conversely, will I be the only one who DOES look like an Instagram influencer?)

The curiosity is understandable, but the panic is unwarranted. Still, it’s important to arrive with the proper perspective to really get the most out of your visit.

Island House is often loosely described as tropical resort-meets-bathhouse, but that’s a clumsy description at best. There are certain areas of Island House that are definitely more “cruisey” than others, but the exact proportion of (welcome, consensual) sleaze and luxury varies wildly depending on the person and what you’re looking for.

If you’re after sex, you definitely don’t have to look far. You can spend your time at Island House without once opening an app and still find plenty of fun. (In fact, the few times we opened Grindr or Scruff, we ended up talking to someone who was also sitting at the pool.) For a resort that offers free 24/7 porn channels in every room, the randiness that permeates the property should come as no surprise.

The beautiful, heated pool is the epicenter of Island House. On Sundays and Wednesdays, they host massive naked pool parties, which attract not only guests but tons of locals as well. Most people go naked, but certainly not all. It’s perfectly acceptable to keep your swimsuit on, but, in our experience, it’s tough not to get swept up in the liberated energy.

Although there is eye-candy aplenty, the vibe is more mixer than orgy. One of the most striking things about Island House is just how casual the nudity can be. It’s difficult to imagine making the typical small talk with people you meet on vacation while your dicks are floating in a pool surrounded by hoards of hunky men, but there’s something really special about it as well. There’s a heightened intimacy that makes even the most casual conversation feel a touch more authentic.

While it’s not unheard of to see a couple (or group) getting to know each other around the pool, the scene is often more celebratory than sexual. The pool’s proximity to the resort’s well-regarded café and restaurant keeps the action at a comfortable distance, especially during peak daytime and early evening hours. At night, it’s more common to see folks getting friendly on the sundeck and poolside loungers.

Don’t let that fool you into believing this is the kind of place that’s dripping in fluids and necessitates keeping your shoes on the whole time. The staff at Island House has seen it all, and their commitment to maintaining a pristine property with a pleasant attitude and no judgment only enhances the joy of indulging in some of your wildest fantasies. (Plus, with heavenly, cloud-like beds in every room, a lot of guys would rather take the party back to their own private quarters.)

The two hot tubs are a bit more steamy. Under the cover of the bubbling surface, friendly hands and flirty feet engage in silent negotiation while guys maintain swan-like grace and calm above the water. The tubs’ smaller size and circular setup encourages more conversation than the pool, and the typical hot tub crowd is a mix of jovial drinks, good conversation and the occasional break in the party to let the bodies do the talking. Like most areas, things pick up at night. (In case you were wondering, ‘What is the maximum number of men that can give you a handjob at once in a hot tub?’ It’s five, the answer is five.)

The steam room and sauna are also popular hookup spots, similar to what you might experience at a bathhouse in other cities. If you’re not in the market for a little meat, there are plenty of times you can have the tubs, sauna or steam room all to yourself to just unwind.

That’s true for anything at Island House. While the atmosphere empowers guys to maybe be a bit more bold than normal with their intentions, it’s also a vacation spot first, and there’s no pressure to engage or not engage in any activity. The only place at Island House exclusively for sex is the (in)famous Red Room. Also know colloquially as “The Library” or “The Cultural Center,” the dark, labyrinthine collection of booths and a communal room with … I guess you would call it a “sex bench?” (I can’t believe I Googled this) … in the center. For those not interested in certain carnal delights, it’s the one place to avoid. For those familiar (and the curious), it’s worth taking a spin through after one of the aforementioned pool parties to at least see what it’s all about.

It’s possible to spend your entire time at Island House bouncing from room to room (and lap to lap) fulfilling fantasies. (This is a good time to remind everyone to be responsible for their own sexual health, whatever that looks like for you.) However, between the all-male clientele, complimentary happy hours, popular parties and other amenities steps away from your comfy bed, a stay at Island House is worth the trip even without the prospect of a good pounding or two (or ten).

A common question is, ‘Will I even want to have sex with the other guests?’ And the answer is, I don’t know. Unlike a lot of gay spaces, twinks, bears, daddies, polar bears, wolves, pups, geeks, jocks, tops, bottoms, singles, couples, thruples and every other stripe of the rainbow are welcome at Island House. The exact mix is going to depend on the day, but there’s likely to be someone to satisfy most tastes.

And for those who are worried about being subjected to seeing someone they aren’t attracted to simply existing in the nude: Yeah, this probably isn’t the place for you. (Though, if you know a vacation spot that only caters to guys you personally want to have sex with, please send me that recommendation!)

However, if that’s your attitude, Key West as a whole might not be for you.

The magic of the island is its independent spirit. They proudly boast the island (and its inhabitants) are “close to perfect, far from normal.” That’s especially true at Island House where there’s a distinct #goodvibesonly energy that makes everyone — regardless of size, shape, age, etc. — feel comfortable.

Plus, who could be shady soaking up all this gorgeous sun?

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