KEY WEST - May 2014 - © Mark O'Connell (959)I had just proposed to my boyfriend over the phone from Key West, Florida when a skinny silver-haired pavement philosopher named Durf caught my eye with a “wanna see what I do?” invite. Elated by my man’s answer and an overwhelming experience on what is the Florida Keys biggest and most glittering of baubles I too offered a firm “yes”. Durf instantly sat cross-legged on the kerb between two parked cars and produced a flat pane of wood and a magnifying glass. Possibly endorsing a mantra written on his own pushbike – “Key West – where the weird go pro” – Durf proved that the Key West weird can also go beautiful as this literal burning man continued a magnifying glass sun-seared portrait of John Lennon onto the idle piece of wood. And with no need for a dollar tip or faux interest on either side, the encounter was over.

Despite its growing scene and historic queer pockets, the state of Florida is not historically known for its LGBT tolerance. The infamous orange juice magnate and crucifix licking Anita Bryant became one of America and Florida’s most famous homophobes in the 1970s (and in turn gave the queer scene a great, inadvertent platform to prove her sentiments wrong). But things change. Even America. And even Florida. So leading that particular march at the southern tip of the United States is Key West – the lowest hanging glitterball on the American map. And just like Durf and his John Lennon portraits, it is not afraid to put its gay culture under the magnifying glass and let the sparks fly.

Just 127 miles off the Miami coast, Key West is nearer Cuba than mainland America and shares the climate and flora of the Bahamas. It is estimated about a third of Key West’s population identifies as LGBT, with the other two thirds possibly identifying as not bothered. Pink icons Divine, Sylvester, Grace Jones and Madonna would appear at the now-gone disco havens The Copa and The Monster, long-term resident Tennessee Williams penned landmark works in his Duncan Street pad, a significant 1980s tourist push fuelled predominantly by LGBT businesses taking a punt on ailing streets and premises gave a renaissance to the island, openly gay men and women are elected to political, police and civic office without fanfare (the Key West of the 1980s boasted one of America’s first out gay mayors) and today it is estimated nearly a quarter of a million LGBT folk a year visit from around the globe.

There’s a sort of Saturday-whatever-the-day feel to Key West. Moped-straddling tourists clutch half-quaffed Mojitos as they weave through the chilled tsunami of mopeds and push bikes, palm trees stand sentry over gingerbread timber cottages with wraparound verandas and freshly rolled cigars are as plentiful as the keynote roosters crossing the road like feathery drag queens on the 5am walk of shame home. Boasting a near Caribbean climate (there is no winter as such) and flanked by the Atlantic and Gulf of Mexico, Key West may well be only four square miles in size but climate and attitude facilitate plenty of year-round allures.

Gay Spring Break, Kamp Key West, Key West Pride, the SMART Ride, the annual LGBT Cocktail Classic Competition, Fantasy Fest, Tropical Heat, Womenfest, the Headdress Ball and Hot Pink Holidays are just some of the more official circles on Key West’s gay calendar. Often spearheaded by the LGBT Key West Business Guild (whose welcoming Information Centre on Truman Avenue comes with its own must-see, free and camp-as-Christmas Tennessee Williams exhibition), these wholly inclusive events are testimony to Key West’s commitment to celebrate not tolerate. And it doesn’t take much for a celebration in Key West.

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Often at the epicentre of these events is the popular Island House resort. Habitually heralded by the likes of OUT Traveller as “the best gay resort in the world”, Island House is an all-male, timber-decked enclave of contemporary and sizable rooms with all barely a towel flick’s distance from a pool and its well-equipped bar, food, hot tubs, steam rooms, gym, sundeck and sarong stash. The clothing optional Island House welcomes non-residents (as do many of the key B&B’s) and is often the happy hour launch pad for many a raucous night on KEY WEST - May 2014 - © Mark O'Connell (566)the Key West tiles. Likewise, the Equator Resort and Alexander’s Guesthouse are notable pins on the LGBT hotel map with an equal focus on poolside hellos, hook ups and cocktails. Equator possibly caters for more of the male traveller, his partner and any new friends that might be collected along the way in that glass bricked hot-tub, whilst Alexander’s Guesthouse and Lighthouse Court have a fresher, more bespoke slant and perhaps a more inclusive clientele that bucks the [sometimes] male demographic of Key West’s scene. Lighthouse Court was a striking base for this writer with its émigré fixtures, canvas canopies and lush greenery. Ernest Hemingway’s elegant home and nearby mid-19th century lighthouse are neighbours – with the latter becoming my really useful marker when doing that walk of shame home alongside those roosters and the former becoming a tranquil, iced-coffee-in-hand antidote to the revelries of Duval Street only a block away.

Should you not want to walk – though it is sometimes the quickest way to navigate the connecting back-alleys and witness the flourishing Bahamian vegetation, side bars and pop-up eateries – local companies offer easy moped and push bike rentals. Though please remember some bicycles’ reverse brake mechanism as this cycle-novice writer didn’t and nearly had to do some major back-pedalling when almost crashing into a loaded hearse and its mourners wending out of an episcopal church. With a camera in hand meander on foot from Duval Street’s main drag of bars, wine and song to Mallory Square’s family and sunset skewed plaza – a sort of 1950s Disney take on a Cuban precinct. Or go in the opposite direction and literally walk to the southernmost point of America and witness the southernmost line of tourists waiting to get a southernmost snap of themselves being southernmost. There is something gloriously yesteryear about cycling through Key West, seeing your passing reflection in the bay window shop fronts, checking the small planes overhead as they soar the line of the telegraph wires and throwing that new shirt into the basket for him back home. Assuming you do not rise to kerbside bar-flies jokily suggesting one challenges the neighbouring car to a drag race start when the lights change – I did, and lost – the bike option is much recommended. As is remembering where you’ve parked said bike after a few early evening libations at the island’s many drinking holes.

KEY WEST - May 2014 - © Mark O'Connell (789)Of course the Bourbon Street Pub complex is now a Key West gay classic with an ever unfurling array of drinking zones, dance-floors, outdoor pools, hot tubs, bars and carpeted split-level sundecks. One spacious bar houses the nightly go-go dancers – a smiley, ever rotating mix of ‘Men of Bourbon’ carefully navigating folk’s drinks and comfort zones like a laser-lit, Yo Sushi chorus line. It would be a lie to say we didn’t pocket a dollar or two away (to see just where some tattoos ended) but it is all done with a knowing wink from a uni-twink or two just “working their way through college”.

The Key West Pub is a brand new LGBT drinking pin on the map and provides the best Dark & Stormy cocktail (I know because the writer pals I was with got me one on engagement day and I have yet to find one as good – and I have put in the field work, believe me). The drag-sync circuit is ably served by 801 Bourbon and the Aqua nightclub and its fierce queens, the Aquanettes. Despite a seemingly regular crowd of out-of-town college girls and hen nights hard at work Instagramming just how queer-friendly they are, the likes of former Miss Gay America Maya, the gymnastic Elle and her fellow Aquanettes ably hold court.

And just behind 801 Bourbon is Saloon One and its Friday night Cock Shock – a veritable appendage ‘competition’ far less daunting and tawdry than it sounds. This writer believed the morning-after prizes on his bedside table were for “most travelled” member – which made reassuring sense as my journey from London and a flash of the passport was surely enough to bypass any podium displays of said appendage. When the vodka and cranberry clouds cleared a few days later I remembered there was a “ginger prize” too. And I may have won that. Here’s hoping the judging criteria at 1.30am was clutching at straws and nothing else. But that is the allure of Key West. The wheels come off. And often stay off.

Key West’s most striking attribute is easily its vibrant sense of community. There is an infectious passion to the restaurant, bar, hotel and shop owners. It is predicated on a pride of produce, a pride of location and a pride of community. The eateries particularly are not always awash with tourists. These are places everyone goes to – locals, workers and those keen just to hang out. Of course there is an influx of folk at the weekends. But one of the inadvertent spectator sports is watching the straight, middle aged rocker couples slowly falling out as she wants to stay and he has realised there are gay bars on all sides.

Food wise, at the more lavish end is the palatial Pier House and its Harbourview Café. The deck seating, syrup-hued evenings and the Crispy Tailed Yellow Snapper with jasmine rice is a beyond sexy combo. As is the marina backdrop to any lunch at the Hyatt Resort and Spa – a veritable game-show prize of moored yacht indulgence and recovery cocktails. More low-key is Square One – the restaurant legacy of a gay couple who worked up its reputation before moving on but have left one particularly skilled veteran barman Patrick (known brilliantly as Patticakes) who can spin up a mean Manhattan to flank your crab-cakes and shrimps. Aside from the family run Abbondanza Italian restaurant and its nifty cannelloni, one of this trip’s dining highlights was easily the pared down but no less polished Flaming Buoy Filet Company. Run by Star Wars mad couple Scot and Fred (but fear not – aside from a Boba Fett figurine propping up the bar this ain’t a fan diner), the force is mightily strong with their vision of a neighbourhood restaurant and a pan-seared Fresh Catch with a Banana Salsa and broccoli cake sent from heaven (or Endor).

Wine buffs are notably served, with restaurant and wine bar staff very agile at explaining the reasoning behind their best bottles. VinO on Duval is a sprawling, elegant example (with a great hidden door switch for the restrooms – well, it was great after that second glass of Merlot); as is the insight of Mark Certonio’s Lush bar. The quietly passionate Mark has not only created the annual Key West Food & Wine Festival (January-February), but also hosts a fascinating chocolate bean-to-bar experience at Lush with carefully chosen wines to augment the chocolate tasting, and vice versa. Provided with a hot pestle and mortar, crushed cocoa nibs, butter, chipped fruit and Mark’s savvy palate, the chocolate bar creating and wine tasting session at Lush is a full-on workout of the senses, arm muscles and preconceptions. And you get to take your efforts home with you.

Likewise, Paul Menta’s First Legal Rum Distillery is a blessing for the rum and Coke fans. Aptly housed in a former 1903 Coca-Cola bottling facility, Menta’s workplace and zeal is equally addictive. Flanked by pipes, coolers, barrels, gauges and all manner of fine-line physics, Menta’s distillery is a lesson in patience and knowhow. See, it’s that passion again.

Hot on the notion of protecting and promoting that “community” is Kate Miano. A welcoming firecracker of a Key West hostess, Kate owns The Gardens Hotel – a graceful tropical retreat of luxury Bahamian style apartments and gardens. The likes of Oprah Winfrey and George Clooney fill out the guest book and a Sunday gin, jazz by the pool and maybe another gin is a local favourite for residents and non-residents alike. Miano will read out local notices and announcements, underlining that sense of community and you realise you have bumped into a lot of faces twice already (though hopefully not at Cock Shock). Another similar drinking hole is La Te Da. A restaurant, hotel and cabaret venue (the beautiful upstairs Crystal Bar is worth a reservation or at least a look), La Te Da is a hardwood and check-tiled social marker boasting high-end drag and cabaret performers, a lobby piano bar and classic Conch dining. La Te Da is also where the chattiest, friendliest women seem to be found and is all the more refreshing for it.

Duval Street particularly (where the majority of rainbow flags hang) has maybe the more diverse array of shops, stores and art galleries. Yes there are the ubiquitous beach shops shifting plastic and nylon, but Towels of Key West is now stocking a great range of original vintage tees designed by the owner Kent Henry (including bygone airline logos with Florida links – such as Pan Am), Graffiti is a flashback-dream of belts, trainers, shirts and delicious satchels and Evolution stocks the Long Lost Tees range of fresh eyed t-shirts and logos from the island’s 60s and 70s clubbing, air travel and bar heritage.

Like all islands, Key West – or Bone Island as it used to be historically known (oh the schoolboy sniggering we had when ghost tour guide David Sloan asked why that might be) – has a water culture that informs and steers the island. This is still a key dictated to by the elements. But assuming they are on side (and they usually are), take the time to explore the waters. The team at Lazy Dog took us on a glorious, hangover-busting kayak trip through the mangroves. From someone who it seems cannot stop a pedal bike, taking to the iguana flanked waters could have posed dicey. But under the relaxed tutelage of the Lazy Dog team this became a seriously great chapter of the trip as a detailed kayaking tour of the crabs, jelly fish, sponges and birds of the mangroves and environs soon unfurled.


A slightly grander [gayer] trip is the rainbow flagged Blu Q cruise. A predominantly male only trip, this is nevertheless an energised sail out onto the dolphin-flecked Atlantic with snorkelling, kayaking, lunch on a sand bar or doing absolutely nothing as options. There is something fairly addictive about pounding along with Michael Jackson’s Off The Wall album at full blast, clutching a Sangria and mentally sticking two fingers up at the sedate boats and married passengers realising the rainbow flag means a boat load of scantily-clad gay pirates who will pounce – or flounce – at any time. Of course like a lot of Key West the Blu Q trip has a clothing optional element but I didn’t partake – mainly because my prize-winning Celtic ginger undercoat would not have benefitted from such snorkel and flipper accessorising.

Equally exquisite was possibly my highlight of the entire trip. Danger Charters (who are anything but) mount a nightly Wind and Wine Sunset Sail into the Gulf of Mexico on a bygone schooner. Never one to get totally excited by sunsets (Key West is very proud of theirs), I had my mind changed in, well, the time it took for the sun to descend quite spectacularly onto the ocean’s horizon. Attended to by the lovely Amber and her lush platter of fresh hors d’oeuvres, the sunset sail is marked by at least seven individually sourced wines, beers and Champagnoise. With plentiful top ups and a realisation why the skipper asks all passengers to keep hold of the ropes when standing, this final night trip was the stuff of pipedreams you never realised you had. That syrup-hued sunset, petrol blue waters and the timber silhouettes of fellow schooners was beyond incredible and easily the greatest visual gift the keys gave me (aside from one or two of the tattooed go-go boys at Bourbons and maybe a chicken literally crossing the road).

Key West is within quick reach from Miami International Airport. American Airlines operate their uber-easy Eagle service for the final leg and the small Key West Airport is a pared-down delight of a cute terminal with at least one hot security frisker one should try and make a post-fluffing beeline for. Key West is a place of great privilege – with perhaps the utmost benefit being the people you will meet. It is a soul-feeding glitterball hanging off the coast of Southern America, a brassy mistress of an LGBT destination.

KEY WEST - May 2014 - © Mark O'Connell (887)

With thanks to Steve Murray-Smith, Carol Shaughnessy, Jo Thomas, the Key West Business Guild, the Florida Keys & Key West Group and KBC PR & Marketing. And of course Douglas Baulf, Kenny Porpora and Collin Spencer.

For further information, or to visit Key West, go to:

This article originally appeared in Beige magazine.

All photos © Mark O’Connell