Checking in at Key West’s Island House gay resort was a bit like arriving at a fancy dress party without a costume. Only the suits being worn at this popular ‘clothing optional’ hotel were the ones the guests were born with.
I’d never considered myself reserved but being forced to make idle chatter about the weather with a fully nude gentleman’s crown jewels dangling pendulously within eyeshot turned out to be the perfect barometer for how prudishly British I really am.
The idea of casual nudity had strangely always appealed to me. What could be freer than casting off the shackles of fashion and clothes for one glorious moment in the nuddy?
But faced with the prospect of baring all in the company of dozens of horny gay holidaymakers, I was filled with Victorian urges to cover every inch of flesh with thick, black cloth and wear a veil.
However, if there is any place in the US where hanging out refers not just to the blissfully glacial pace of life but to quite literally shooting the breeze where the sun don’t shine, then Key West is it.
America’s southernmost point is geographically closer to Cuba than the nearest Wallmart and culturally closer to the swinging 60s with its anything goes attitude to life, sex and rock ‘n’ roll.
Which is not surprising considering its history as a Mecca for hippies, artists and writers including Ernest Hemingway and Tennessee Williams.
And it’s this ‘come as you are’ outlook to life which attracted the first gay visitors to this tropical paradise in the 1970s.
These fresh-water Conchs (the name of newly arrived Key West residents) helped restore the thousands of dilapidated Victorian houses to their former glory.
‘Close to perfect – far from normal’, read the tagline on the brochure handed to me at the hotel. Already feeling like Alice tumbling down the rabbit hole to sexually liberated wonderland, I was inclined to nod in agreement.
While my partner of 10 years and I weren’t quite ready to sling our keys in the bowl and swing in the hotel’s ‘erotic video lounge’ we were happy to dip our toes in Key West’s main attraction – its pristine waters.
Be warned, this two-by-four mile rock in the ocean is not for beach bums and bathers. Away from the bars and restaurants on Duval Street, paradise here is found on or indeed in the open water.
From snorkeling, sea kayaking and dolphin safaris, there’s no end of ways to get wet.
However, eager to let go of my inhibitions and even perhaps unlock my inner naturist, I joined Barefoot Billy’s 90-minute tour of the island…on a white-knuckle jet ski.
It may be fast and furious, but believe me, there’s no better way to see Oprah Winfrey’s luxury Sunset Key villa than skimming the waves at more than 40-miles an hour, with your heart in your throat and your lungs aching from screaming to go faster. It’s an adrenaline junkie’s dream.
With my need for speed fulfilled, a sunset cruise on the traditional Schooner Adirondack III served the perfect antidote – champagne, cheese and a golden sun dipping seductively below the horizon.
Maybe it was intoxicating sea air, or the three glasses of bubbly, but after a hearty dinner of conch fritters (a must-have local delicacy), lobster tail and oysters at the Half Shell Raw Bar in Schooner Wharf, I felt an ease and contentment which I realized comes with not only enjoying an extended vacation but from actually embracing life, instead of fighting against it.
Key West’s famous ‘Carpenter Gothic’ gingerbread houses tucked under swaying palms or giant leafy fruit trees add to the city’s laxidasical charms.
But make no mistake, beneath its laidback veneer is a bawdy drag queen just screaming to get out and when it comes to naughtiness, Key West pulls no punches. From pulsating gay dance clubs to testosterone free women’s bar, anything goes.
Where else would you find an inebriated drag queen in a giant ruby slipper being lowered into a crowd of rowdy revelers at New Year? Or the 10-day Fantasy Fest carnival in October where both locals and visitors let their hair down even further with a flamboyant fancy dress parade and a party to end all parties?
Returning to the hotel with a newly found zest for life, I felt ready to maybe finally shed not only an inhibition or two but maybe even a layer of clothing.
After gingerly maneuvering past the spread legged nude waiting expectantly outside our room, I locked the door and let the clothes plunge dramatically to the floor.
After bowing to an imaginary round of applause from the suggestively posed men in the paintings positioned inescapably around the room, I hesitated.
What if the world wasn’t ready to see all that Matthew Jenkin has to offer? After all, my mother always told me you should leave at least something to the imagination.
So, Key West or not, I sauntered confidently to the pool proudly wearing one item of clothing – a pair of trunks.
After all, you can take the boy out of Britain, but you can’t take reserved, clothes-loving Britain out of the boy.
For more information on gay life in Key West, click here.
Getting there and away
Key West’s airport has regular daily flights to and from Miami in Florida, which in turn serves international routes to most countries.
However, like all great adventures sometimes the journey is half the fun and Key West is the last stop on a jaw-dropping ocean highway connecting the islands to the mainland. It crosses over 15 bridges, the longest being seven miles long, and at times runs parallel to the now crumbling Florida East Coast Railway. Watch the road but remember to soak in the stunning scenery.