The Island of Misfit Boys

My first impression of Key West, Fla., was the wild cock. Literally, cocks and chickens run wild through this tiny, historic island town, situated in the heart of the Florida Keys. It was the first sight I saw after leaving the tiny airport, about the size of a two-story motel, and catching a ride with my guide for the week: a jolly, mustachioed queen named Chris.

“Yeah, the chickens were brought on ships in the 1800s,” Chris explained as we drove past rows of pastel-colored bungalows, tropical palms and more packs of feral chickens. “The early settlers used to eat them, but now they just roam wild. You get used to them after you’ve lived here for awhile.”

Chris had graciously offered to pick me up and drive me to my lodgings, a clothing-optional gay resort I had chosen out of a brochure. He saved me from paying for a cab — which, by the way, are all colored pink, “Not because they’re gay,” Chris explained, “It’s because that’s the color of a conch shell, and our nickname is the Conch Republic.”

Then again, no one would bat an eye if the island’s taxi fleet did color their vehicles pink solely to attract visiting gays. Provincetown and Fire Island may be the gay meccas of the North, but south of the Mason-Dixon, you can’t get much gayer than Key West.

Just how gay is it, you ask? The locals hang rainbow flags from front porches on nearly every street here; the crosswalks downtown are painted in rainbow colors; and even the Build-a-Bear Workshop on Duval St., the town’s main tourist strip, spells its name in rainbow lettering and employs actual bears.

“The old queens know this as one of the places that you go,” Chris told me, “You know, the dyed-in-the-wool LGBT from the get-go, type. Course, what’s happening now, with the world opening up to the LGBT experience, you’re finding more places that are willing to market to us. And where there used to be only four or five places on the map that you could go on holiday, there’s now over a hundred.”

True, by the ‘50s, Key West was one of just a handful of places in the world where two men could walk down the street holding hands and not get beaten or heckled. Actually, two men walking down the street holding hands would probably be one of the last things a visiting Evangelical might consider stoning in the streets of Key West, where nudity, open containers, and pot-smoking drag queens are all part of the local flavor.

It’s also true that LGBT tourism is ballooning all over the country. Las Vegas, Nev., for instance, spent about a million dollars last year on ads aimed at attracting the LGBT community, but Chris says he isn’t worried. After all, Key West is one of the originals, and you still can’t order a drink to-go in Las Vegas.

The lodge

No one seems to know how, exactly, this tiny island turned into a little slice of gay paradise on earth. Some say it  started with Tennessee Williams, the gay playwright who helped put the island on the map when he bought a modest home here with his partner in the 1940s. Others say the remote location offered gays an escape from the bigotry and persecution they often faced on the mainland. Maybe the gays are just naturally attracted to the Keys, considering how closely they resemble seminal fluid leaking out of Florida’s dong-shaped peninsula.

Whatever the reason, scores of gay men have called the island home for more than a half-century, and a vibrant arts and tourism industry has sprung up around them.

I was to spend my week at Island House, an all-male, clothing-optional resort on the northernmost tip of the island’s historic district. I had never stayed anywhere that was clothing-optional, the exception being an apartment I shared with a couple of hippies in Boston, Mass., and I figured I’d take the option with clothes for at least the first day or two.

Chris and I checked in with a very nice receptionist named Alan, who handed me my room key and gave us a tour of the premises. There was the naked pool, the naked hot tub, the naked sundeck, the other naked hot tub, and the gym — the only place in the resort where shorts are mandatory. Sure enough, while some guests wore shorts and tank tops, many more opted for Speedos, or nothing more than towels wrapped around their waists, to be unwrapped later while lounging by the pool.

As Alan unlocked the door to my room and swung it open, I was greeted by a large oil painting of a grizzled muscle man, all in the nude, staring heroically out of a gilded frame. Yes, I thought, this would do just fine.

Alan left a few flyers on the bedside table and bid me a good stay. Chris, too, had some errands to run and wanted to give me time to unpack and settle in, but before leaving, he sat me down, a stern look on his face.

“Listen, Nick.” He said, his mustache pulled to one side, “Make sure you see other parts of the island. There’s so much stuff to do out there. We’ve had journalists check into ‘Island House’ before, and some of them never check out.”

I laughed and assured him that wouldn’t be the case. My editor wanted an article with some family-friendly content in it, after all. I showed Chris the door, unpacked a little, and began mapping out my itinerary. Maybe paddle boarding through Florida’s mangrove forests would make a fun experience. I flipped through some brochures and found a couple options. I picked the one with a naked man in the picture. The ad said “clothing optional.” Oh well, I thought. If the paper really wanted family-friendly content, it should have sent me to Disneyland.

That night, I dreamt of a feral chicken getting drunk off Manhattans.

The excursion

My paddle boarding instructor proved to be one of the nicest people I met that week.

His name was Cody. He lived in New York before moving to Key West with his boyfriend about five years ago.

The first several minutes we spent on the water, we knelt on our boards and paddled Pocahontas-style. After some time, Cody stood up on his board. I managed to straighten out my legs and lift myself up without falling off, too.

Some time after that, Cody pulled off his swim trunks and gestured to mine. “Feel free to feel free,” he said.

I pushed my swimsuit down to my ankles, but there was no way I was going to lift my feet up from where they were firmly planted on the board. The air around us was warm enough, but the water was ice cold, and I had no intention of losing my balance.

We continued like this for another 10 minutes, gliding down the serene waterways carving their way through lush thickets of mangrove forest — him with a cooler of snacks and sunscreen on his board, me with my swimsuit around my ankles.

We navigated through wide channels, narrow side streams, and, during one part of the tour, through a particularly thick tangle of mangrove trees so dense we had to lay on our boards face up, grabbing onto branches to pull ourselves along.

Cody pointed out various inhabitants of the forest as we passed them — jellyfish, sea sponges, little tree crabs, a giant orange iguana lazing about in a mangrove. In one shallow clearing, he reached down and plucked what looked like a finger-sized turd from the sea floor.

“It’s a sea cucumber,” he said.

“Oh! I never realized they were so small.”

“Well, it gets bigger,” he said with a smirk.

Later that day, back at the Island House, I would recount this story to a gaggle of drooling queens.

“Did anything happen between you two?” one asked, almost immediately.

“No! Of course not,” I said, “I’m not one of those reporters who sleeps with his sources.”

“Well I’m surprised,” said another with double-pierced ears, “Everything in Key West is pretty cruisy. Seriously, you can get laid just going to the supermarket.”

The table gave a collective belly-laugh.

Then the man turned to me. “By the way, we’re all hitting the bars tonight. Are you joining?” he said with a lilt.

The wreck

Make no mistake, there’s plenty to do in Key West that doesn’t involve getting piss-drunk. The town has a decent theatre scene — “Mothers and Sons,” a show about first-time gay parents, was playing when I visited. There are lots of sightseeing tours too, and plenty of good restaurants serving key lime pie and various dishes featuring conch (my personal favorite being Caroline’s on Duval St.)

But there are just as many, if not more, activities focused on binge drinking. You can book a sunset “booze cruise,” or get drunk watching a two-hour long drag show, or just walk in a straight line until you end up inside a bar — they must have over a hundred here.

The town was celebrating Mardi Gras the week I visited, and because I’m always up for an adventure, I joined the men from Island House and rejoined my guide, Chris, for a Mardi Gras-themed pub crawl, led by a drag queen in a sequined dress and her two twinky escorts in rainbow fox tails.

I was under the impression we’d only hit five or six bars that night, taking a free shot at each, then parade through the streets, pelting pedestrians with plastic beads.

So by the time we reached bar number four, a sleazy gay establishment called Saloon 1, where gay porn played on the televisions and a dark room towards the back had the words “Cum Bucket” spelled out over the doorway, I was feeling pretty good.

“Remember to pace yourself,” I recall Chris telling me, “We’re not even halfway done!”

“Not halfway done?” I sputtered.

“We still have 10 more bars to go,” he said.

The most I can recount from later that night is meeting an older gentleman named Joey, who owns most of the gay bars in Key West, and getting an exclusive tour of the balcony above Bourbon St. Pub, where they keep a single giant high-heel shoe — on New Year’s Eve, they lower it with a drag queen seated inside. I also remember eating crawfish with a stranger. It’s possible I may have kissed a woman too. I also seem to recall running down a dark sidewalk alone, and knocking down a bike rack. Somehow, through the grace of God, I suppose, I ended up in my own bed sometime around 3 a.m.

“So how was your night, sweetie?” The Island House bartender, Ralph, asked me the next morning.

“A glass of water and some Advil, please,” I replied.

He laughed. “Sounds like you had a true Key West experience, baby.”

Land of the free, home of the gay

On my last day in Key West, I met up with Nathan Gay (real name!), who used to be editor of Celebrate!, the island’s now-defunct LGBT newspaper. Like myself, he’s native to North Carolina, but he doesn’t look like your typical conservative Carolinian. When I met him, he was dressed in purple shorts, a purple shirt and a purple fedora he crafted out of a hundred purple pipe cleaners.

“North Carolina was great,” he said, “but I just seem to fit in so much better here.”

He remembers coming down the Key West for the first time 13 years ago and realizing how different things were in the Keys. “It really blew my mind to think, this is how life could be. I could really live my life like this,” he told me.

We talked about the Key West motto, adopted by the city in 2000. It reads: “One Human Family,” and it’s particularly apt for this weird, eclectic community of queers. So you get turned on by people of the same sex? So you’re a guy who likes to wear women’s clothing? So you want to walk down the street wearing nothing but pirate boots, striped shorts, and tassled pasties? Hey — as long as you’re human, you’re part of the family!

I only had a few minutes to talk with Nathan before I had to leave to catch my flight back home.

“Don’t worry,” he told me as I paid for my coffee and checked my flight time, “you’ll be back. They always come back.”

I was already part of the family.

 

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