Visiting Island House: Beyond the Beds, Boys and Booze at Key West’s Gay Paradise

I Missed Being Around Gay People

After 18 months of canceled Pride celebrations, postponed weddings and more sourdough starters than sunshine, my travel bug had grown to Dune sandworm-sized proportions. Without so much as a weekly Drag Race viewing at the local bar, I didn’t just miss the world outside my sofa; I missed being around gay people. I didn’t need to merely go somewhere gay-friendly, I needed to go somewhere gay-saturated.

And there’s no destination gleefully gayer than the renowned, all-male, clothing optional resort, Island House.

(It doesn’t hurt that it happens to be located in the idyllic island paradise of Key West.)

A short, direct flight from NYC got me into town early one Monday morning. The island’s tiny airport is the first indicator to visitors they’ve left the drudgery of their origins behind for something different. Walking across the tarmac (there are no jetways), you see a replica of the southernmost point landmark and large figurines that look right out of Squid Game under the words “Welcome to the Conch Republic.” It’s a cheeky nod to the island’s brief (mostly performative) cessation from the nation, but it’s also an enduring reminder of Key West’s proud independent spirit and uncompromising weirdness. 

The island embraces uniqueness with its more-than-a-marketing-tagline “Close to perfect, far from normal” ethos. It’s on display with the drag queens down Duval, at the annual Fantasy Fest and even in City Hall, where they proudly installed Florida’s first openly-lesbian mayor, Teri Johnston. The local queer community is woven into the DNA of the island, from politics to business leaders and artists, but the central hub for gay life in Key West is Island House.

Nestled in Old Town, the resort feels comfortably isolated once inside the grounds, but is just a quick walk to most areas of interest on the island. However, if you’re not up to much exploration, Island House is the perfect one-stop spot for the best, gayest vacation you can get.

Early Arrival

I arrived before check-in and planned to stash my bag and hit the pool right away. The always cheery front-desk clerk told me the room was ready early, but I decided to delay settling in just yet. Even though this was my third visit to the Island House, I always opt for a quick refresher tour when I arrive. The friendly staff at Island House is one of its greatest assets, and this is a great way to get to know the faces you’ll see as you traipse around the grounds in a towel or less. (Plus, when they’re not on the frontlines of the resort’s COVID response, they’re great sources of gossip as you get the lay of the land.)

He led me to my room beside the heated pool, the epicenter of Island House activity. That’s where they host the lively Sunday and Wednesday pool parties, and it’s right beside the resort’s delicious, 24-hour bar and café.

My initial concern about late-night noise keeping me awake proved unfounded (though the luxe, feather-topped bed probably helped). Plus, the convenience of dinner, coffee or a party just a step outside my door felt like an additional layer of luxury. The only downside, I’d come to learn, is everyone enjoying the social scene by the pool witnessing all the comings and goings from your room. 

Despite feeling like an Island House veteran, I immediately made a rookie mistake. An earlier than expected check-in and the rush of excitement of my arrival inspired a very early start to the cocktails. I forgot how generous the pours are at Island House, but before long, it hardly mattered. The pool filled up with newly arriving travelers for the week, and the gaggle of gays I’d been craving descended on the pool like a flock of waterfowl. 

Traveling solo can certainly be lonely, and not having a wingman with you at a party full of gay men, naked, could understandably sound like a nightmare. However, there’s not a gay bar I’ve entered on Earth (and, trust me, I’ve been to many), that comes close to the level of friendliness and congeniality at Island House. 

When Some Are Naked, Everyone Sheds Layers of Awkwardness

I’m sure the fact some people are naked helps everyone shed some layers of social awkwardness. While it may be the first thing people seem to focus on, nudity at Island House feels much less dramatic in practice. It’s not always sexual (unless you want it to be), and, at least on all of my visits, the various body types and age ranges keep it from feeling exclusionary. There are solo travelers, like myself, couples, friends, even co-workers, so anyone worrying if it’s too sexual/not sexual enough just needs to know it’s exactly what they make of it.

And, unlike many a reality-TV competitor, I was, in fact, there to make friends. I immediately glommed onto a couple of bears from Boston. They were returning to Island House to celebrate one of their birthdays, and they spent most of their trip in the pool ordering rounds of mudslides (which I insisted on calling Fribbles between sips of vodka).

I did at one point remember to eat something from the café between drinks. The food at Island House is famously better than it needs to be. I love the tuna tataki, a generous portion of seared, sesame-crusted, sashimi-grade tuna atop a bed of seaweed salad. Besides the convenience and quality of the food, the poolside seating is a perfect way to enjoy the tropical climate (and great for those avoiding indoor dining). If I wanted to seriously soak up some of these cocktails, though, I’d need something a little heavier. My favorite dish — and a nightly post-drinking staple — is the crispy, fried conch fritters. 

I lost track of the Boston bears and the Fribbles after sundown, but soon the compound effects of that early start replaced the surge of excitement I felt when I first arrived. 

I woke up the next morning feeling distinctly not great. Opening my door to the bright sun shining over the poolside lounge chairs and café, I was greeted by an older guest. 

“Glad to see you’re OK this morning. You looked like you had a lot of fun last night.”

I had, and I appreciated his friendly check-in. That’s community for you. I wasn’t as interested in the subsequent commentary on whomever may or may not have entered and exited my room and when, but I guess that’s what friends are for, too.

A quick, fresh breakfast and hangover-quenching coconut water from the café later, and I was en route to my ride on the BluQ for a male-only, clothing-optional snorkeling and sailing adventure. My friends at the front desk gave me the tip to snatch a towel from the locker room, fill a water bottle and bring plenty of sunscreen. 

I was the only guy aboard staying at Island House, but later that evening, everyone from the boat was there, including the sexy captain. For gay travelers, it’s impossible to resist. The term “Happy Hour” doesn’t do justice to the nightly complimentary top-shelf cocktails for guests. Uninhibited visitors blissed out on vacay vibes mingle with a mix of curious travelers staying nearby and gracious locals enjoying the never-ending fresh supply of men. Since residents are able to buy memberships, Island House feels like a neighborhood watering hole in addition to a world-class resort. Even I, having only spent less than a full month total on the island in my lifetime, ran into a guy I met on a previous trip and made plans for later in the week. Everyone at Island House feels like an old friend, even the new ones.

Of Happy Hours, Handsome Locals, and A Hunk from Houston

During Wednesday’s happy hour, as I chatted trunkless with my handsome local friend, we spotted a fellow solo traveler across the pool. I swam over and hit him with the standard, three-question Island House intro: What’s your name? Where are you from? Where are you staying? He was a hairdresser from Houston with beautiful tattoos, and soon we bonded over Tex-Mex and body art. By the end of the happy hour, we were doing shots and sharing RuPaul’s Drag Race takes like best Judys.

You could easily visit Key West and never see anything besides the pool at Island House and the airport, but where’s the fun in that? Key West boasts tons of natural splendor, funky art and a unique gay nightlife. 

Though, Island House has a way of staying with you, even when you’re off-property. I spotted my Houston buddy across the backyard bar at Bourbon Street Pub the next day. When I managed to score a ticket to one of Randy Roberts‘ legendary drag performances, I found myself seated with the Island House bartender responsible for all those strong pours and the sexy captain of the BluQ (the image of whose naked body had not yet dissipated from my mind). Sometimes I’d just catch someone with one of the resort’s black, spiral keychains still dangling from their wrist and know I’d be seeing them later for happy hour.  It really makes the difference between traveling solo and traveling alone.

At some point, I did have to tear myself away and head home. I bid farewell to the concerned older man from the bar, the hairdresser from Houston, the bears and their Fribbles. I zipped up my suitcase full of swimsuits never worn, and I gave my last goodbyes to the guys at the front desk.

As I waited for my Uber, I thought about the last year, being cut off from community and how nice it was to see Island House still there, gay as ever. 

I took one last look around and ordered a round of conch fritters for the road.

Discover more about Island House and Key West with our previous coverage.