Dusk has descended upon the Conch Republic and from the backseat of my air-conditioned Uber I see the twinkling streetlights of Key West, an occasional passing moped, and on the balcony of one of the cityโs famed clapboard homesโa shirtless stud surveying the sceneย below. Itโs Pride Weekend, and the energy in the air is kinetic.
Key West always romances me swiftly. True, the queer scene is smaller than in P-Town or Palm Springs. However, gay travelers are still very visible and easily stand out among the tourist hordes thanks to pronounced biceps and noticeably less fashion missteps than their hetero counterparts who seem content to walk around wearing baggie shorts, fanny packs, and jokey t-shirts sporting phrases like โDonโt Stare at My Cock,โ a nod to the cityโs ubiquitous roosters. Plus, I love Key Westโs โOne Human Familyโ ethos and laissez-faire attitude toward all who visit.
What Iโll discover this weekend is that most gay visitors alternate between as little clothing as possible and none at all. Reluctantly, I put on shorts and a tank and head to dinner.
Garboโs Grill (409 Caroline St.ย Tel. 305-304-3004. garbosgrill.net) announces itself with a flashing neon sign. Garboโs is a food truck attached to an open-air bar adjacent to Duval Streetโthe cityโs touristy main drag. I order the Cayo Bowl (cabbage, carrots, mango, cilantro, jalapeรฑos, mushrooms and onions) with shrimp and watch as the cashier decorates it Jackson Pollock style in a tangy Caribbean sauce. A black lab lays perfectly still on the restaurantโs brick patio like the victim of a canine crime scene. Surrounding him are picnic tables and a picket fence boasting a sign that reads: Jooicy Tits Vodka.
The Author At The Bourbon St. Pub (Photo by Jason A. Heidemann)
Time to imbibe. Queer nightlife in Key West centers around a cluster of gay bars at the intersection of Duval and Petronia Streets that have been around forever and appear to be going nowhere.ย Bourbon Street Pub (724ย Duval St. Tel. 305-294-9354. bourbonstpub.com) is the most famous of the bunch and boasts a clothing-optional back bar featuring a swimming pool and hot tub. The pool is neatly divided by a volleyball net and filled with beach ball floaties. I remove my clothes, lay them on the concrete and submerge myself in this beach ball bubble bath where almost immediately I begin making out with Jordan, a chubby bottom from Dallas who is wearing a swimsuit (almost no one else is) and says heโll go nude only if I remove it for him. I also make out with Scott, a shrimper with a bushy goatee and crooked teeth who says he’s the only gay fisherman on the island. Later, I encounter a chiseled Kiwi who lives in Australia. Heโs straight but likes all nudist environments, though he confesses the one thing about gay culture that confounds him are glory holes. Around 2 A.M. I join the masses in stumbling zombie-like back to my hotel room. I fall into bed easily and slide a sleeping mask over my eyes.
Friday
At 9:30 A.M. I head to Duval Street and procure several tubes of sun screen and some provisions for a day at sea. Then I make my way to Key West Bight, a bend in the island where numerous sailboats are docked. Aboard Blu Q Catamaran (Tel. 305- 923-7245. sailbluq.com) I am greeted by Captain Smalls, a handsome pocket gay with bejeweled toenails that Iโll later discover match his handmade aqua-colored cock ring. Blu Q is a longtime Key West charter offering sunset sails, all male day sails, and snorkeling tours. Weโre a full ship today, and thatโs a lot of sea men!
Getting Ready To Set Sail On The blu Q (Photo by Jason A. Heidemann)
Itโs 85 and sunny and a gorgeous afternoon to be out on the water. Thereโs so much blue in every direction that itโs difficult to separate sea and sky, though below the horizon the water is a crystal clear greenish-blue while the air above it is turquoise. By the time we reach our sandbar and drop anchor just about everyone has stripped nude and plopped into the sea where they have separated into small clusters and are exchanging โgay handshakes.โย The boat ride back is likewiseย handsy, and if I had to guess Iโd sayย Captain Smalls and his crew loveย their jobs.
Near the docks sits BOโs Fishย Wagon (801 Caroline St. Tel. 305-294-9272. bosfishwagon.com), a legendary Key West food truck withย an attached tin roof supported byย wood beams and decorated withย string lights and license plates thatย have been poorly hammered into theย walls. Chickens are running aroundย everywhere. I order a conch sandwich, which is exactly like a Newย Orleans poโ boy and tastes amazing.ย I learn later that if you ask for theย locals special you get free fries (butย who needs the carbs?).
That night, at Bourbon Pub, I runย into one of my favorite queerย comics. James Adomian is a Losย Angeles-based standup known forย his celebrity impressions andย Getting Ready To Set Sail On The blu Qย voiceover work, but he is also an incredibly precise, perceptive, and hilarious observer of gay life. Heโs appearing all weekend at Comedy Key West (218 Whitehead St #5. Tel. 305-985-7370. comedykeywest.com) as part of a booking happy accident (the straight guy who runs the venue had no idea it was Pride Weekend). The makeshift venue (coffeeshop by day, club by night) offers a good enough stage for Adomian who shines while delivering jokes about opening for Joan Rivers in his youth, bottoming like a middle-aged dad, and searching for tops on Grindr. Check out his YouTube special: โPath of Most Resistance.โ
Later, Aqua Bar and Nightclub (711 Duval St. Tel. 305-294- 0555. aquakeywest.com) is hopping when I enter to Robynโs โDancing on my own.โ Atop the bar is a chiseled dancer in a silver thong whose buns shake like one of those coin-operated Magic Fingers beds youโd find in a hotel room in the โ70s, though I can hardly see his meaty cakes under all that cash. โI donโt know about you but Iโm horny!โ a drag queen in a spandex map-of-the-world onesie says while announcing the eveningโs big eventโa naked towel dance. The gays in the room are hardly aroused by this information, though a group of bachelorettes posing along a row of banquettes like theyโre on a Real Housewives billboard offer rowdy cheers.
Key West Pride 2023 (Photo by Rob OโNeal/Florida Keys News Bureau/HO)
Key West really is a magical place, and itโs unfortunate for most of us that at some point we must leave the island and go back to being a respectable person again. Truth be told, I donโt know if I can.
I barely fit inside Saloon 1 (504 Petronia St. facebook.com/ Saloon1KW), which serves as the islandโs de facto leather/fetish bar and is slamming tonight in anticipation of its weekly Cock Shock contest. A seasoned gentleman named JT who has mutton chops and a ponytail hands me a bracelet which I tell him looks like a c-ring. โI have my cock on my business card,โ he says handing me a double-sided business card featuring his wiener on one side. โI love making the printers do it.โ I offer him a raised eyebrow.
JT is the longtime host of Cock Shock which is divided into 12 exhausting categories (Best Beard, Best Chest, Best Ass, etc.) that drags the contest on a little too long. When he announces Hottest Couple, two Minnesota guys I recognize from my hotel who are married with children make their way to the stage. They are both dashingly handsome and one of them is naked so naturally they win handily (their kids will be so proud!). The outdoor patio is just as stifling as the packed bar and filled with cloud bursts of cigarette smoke. Time for fresh air and food.
Something Iโve come to discover from locals and tourists alike is that everyone raves about Mr. Zโs (501 Southard St. Tel. 305-296-4445. mrzsfranchise.com), a late-night pizza joint right off Duval Street. Their accolades are not misplaced. Mr. Zโs offers the perfect NYC slice: grease free, crispy around the crust, smothered in pepperoni, and served atop a too small paper plate so that the pointy end of the slice hangs over it like a person dangling their legs over the edge of a swimming pool. Itโs the perfect end to my night.
SATURDAY
Glazed Donuts(420 Eaton St.Tel. 305-294-9142. glazeddonuts.com) is the surprisingly uninspired name for the best donut shop in town. Tucked away on a side street off Duval, its inventive flavors include Blood Orange Bulls eye and Salted Caramel Cake. I start my day here and lean into island heritage by ordering a raised donut with Key lime and blackberry crรจme filling. The donut is so good, I occasionally still think about it.
Taking up an impressive one-acre lot in the middle of the city, Hemingway Home and Museum (907 Whitehead St. Tel. 305-294-1136. hemingwayhome.com) is both the biggest and best cultural attraction in Key West. I pay it a visit each time Iโm in town. The home was built in 1851 in French colonial style and features bright yellow shutters and a wraparound balcony overlooking handsome tropical grounds, which are lovely to stroll at an unhurried pace. But the real draw are the knowledgeable docents who spin tall tales of the authorโs turbulent life and the exasperated wives who tried to manage him. โJust assume with every story that Hemingway is drunk,โ says our gay docent as I stand in front of a photo of Hemingwayโs transgender daughter Gloria (then Gregory) clutching Snow White, a polydactyl cat. Dozens of Snow Whiteโs six-toed descendants roam the property to this day, and I realize Hemingway Home is basically the worldโs most literary cat cafรฉ. Our docent says Hemingway had sex with both women and men and often in throuples, a claim that has been verified.
Southernmost Point Buoy (Photo by Mia2you)
Hemingway Home is just a few blocks from the famous and oft-photographed Southernmost Point Bouy (1400 Whitehead St. southernmostpointbuoy.com), which boasts a line of smartphone-wielding Instagrammers stretching nearly a block. As I walk past it, a Midwest cutie who I met on yesterdayโs sailing tour whizzes by on a rented bike and shouts: โWalk of shame! Thatโs the same outfit you were wearing last night!โ Heโs not wrong about the outfit, but having left Hemingwayโs home and heading now to the museum of a playwright giant, this is a walk of literary fame, not post-hookup shame.
At Cuban Coffee Queen (cubancoffeequeen.com) a locally loved staple (multiple locations) boasting a super gay name, I order a cafรฉ con leche and continue my cultural afternoon by visiting the Tennessee Williams Museum (513 Truman Ave. Tel. 305-842-1666. kwahs.org/tennessee-williams-museum), which is not nearly as impressive as Hemingwayโs house. Itโs a small, subdued place (Iโm the only visitor) containing original playbills, photos, signed memorabilia, and reproductions that donโt quite do the queer playwright justice considering he called Key West home for more than 40 years.
I swing by the takeaway restaurant The Lobster Shack Key West (507 South St. Tel. 305-741-7149. lobstershackkw.com) for lunch and order a lobster roll from a sunny, blonde teenager who hands me a perfectly toasted buttery roll and a wedge of Key lime that I pinch between my fingers and squeeze with care atop the chunky lobster meat for added zest. Across the street, I walk along the Emma Carrero Cates Pier where families are lining up to take pix at the pierโs end which is neatly framed by the cerulean ocean behind it.
Key West isnโt famed for its beaches, and I canโt find consensus as to which of the few strands scattered around town is queerest. Iโm told Higgsย Beach is gay-friendly, but there isnโt a Speedo in sight when I check it out, and Iโm not about to strip down to my turquoise Rough Trade Gear swim thong amongst a bunch of straight Florida families. Instead, I visit the Key West AIDS Memorial (keywestaidsmemorial.org) at the inter section of White St and Atlantic Boulevard and enjoy a moment of quiet reflection while scanning the names of the many gay and bisexual men lost to the epidemic.
After a prolonged nap. Iโm requesting a table for one at Mangia Mangia (900 Southard St. Tel. 305-294-2469. mangiamangia.com). Iโm also having gay-jร vu. Everything about this family-owned, corner Italian joint where menu items are made from scratch looks familiar, including the tiled floors, wood-paneled walls featuring pieces of sunny art, and servers dressed in t-shirts that say: Pasta to the People. I realize I was last here with a group of friends maybe 10 years ago. I order broccoli rabe which is chopped so fine it comes with a spoon, and for a main dish I have rigatoni with jumbo shrimp, chopped tomatoes, kalamata olives, prosciutto, and arugula. Itโs so good I eat every bite including the bits of parmesan cheese and chili flakes falling between the tines of my fork and into puddles of lemon-yellow olive oil below. I highly recommend Mangia Mangia.
Key West Signs
Pride parties are happening everywhere tonight, and a sweaty, sticky Duval Street is buzzing in anticipation. At the Crystal Room, a small cabaret theater inside restaurant and hotel La Te Da (1125 Duval St. Tel. 305-296-6706. lateda.com), a rapt audience is clustered in groups around bistro tables while Cher belts out โBelieveโ just feet from us. At least we โbelieveโ itโs her. The chanteuse on stage is female impersonator Randy Roberts who performs a regular cabaret show at La Te Da. Tonight, he executes impressions of Cher and Bette Midler with astonishing precision, right down to costumes, facial tics, and performance styles. Roberts throws in a couple choice swipes at DeSantis (Bette and Cher would approve) which garner thunderous applause. I have a great time.
Afterward, I find myself trying to catch a breeze at a rooftop bar several stories above the erupting nighttime action happening along Duval Street. This open-airs saloon is canopied on one side and surrounded by lush, potted plants everywhere else. A DJ is blasting dance-y tunes, and some folks are cutting loose. The bartenders are pleasant, but also no nonsense, and they maintain a strict no cell phones policy meaning if you whip yours out, youโll get thrown out. But you can whip out just about anything else because Garden of Eden (224 Duval St. Tel. 305- 296-4545. bullkeywest.com/garden-of-eden) is clothing optional.
The bar is crowded tonight with gays and straights alike, and about a quarter of the guests are in their birthday suits. There is a nude smoker lurking in the shadows where cigarettes are allowed, and heโs clearly caught another dudeโs eye (eventually, they leave together.) Two shirtless hunks are dancing together, while another gay duo sit on a nearby bench with their knees touching. About half the women in the room are topless and the straight New Zealander I met two nights ago at Bourbon Pub is also here naked as a jaybird. I catch the eye of a dressed dude who is cutting the rug with his friend group, though I canโt tell if heโs gay or not. I hope that removing my shirt (and eventually my shorts) will entice him and eventually it does. I learn that heโs visiting with his husband and two friends, but to no avail all his clothes stay on.
I return to Bourbon Pub, and itโs packed. A party called Purgatory is happening in honor of Pride weekend and the men-only back bar is open tonight to everyoneโand everyone is here. The dance floor and swimming pool are full of men and women both gay and straight.
A machine sitting off the dance floor is spitting out large quantities of foam and piling it so high itโs reaching eight or nine feet in some places. Curiosity gets the better of me and as I wade through it waist deep I encounter a curly-haired cutie in a white Papi jock strap. โDaddy,โ he whispers softly, initiating an encounter. When he gets down on his knees, he disappears completely in a sea of bubbles, but Iโm ecstatically aware heโs found what heโs seeking. I emerge minutes later covered in suds and beeline it toward the outdoor shower to rinse off.
SUNDAY
Iโm circling the pool at Island House Key West (1129 Fleming St. Tel. (305) 294-6284. islandhousekeywest.com) with a single thought: please let there be a lounge chair available. The legendary men-only, clothing option al guesthouse has swung open its door for a naked disco pool party and I bought a guest pass. I love this place so much that I used to tell other gay guys that if Island House is booked, donโt bother visiting Key West. Iโve since softened my stance, but Island House really does have it all, including a swimming pool and second story sun deck overlooking it, two hot tubs, a small workout room, a play area, and a 24/7 bar and restaurant serving some of the best food in town. The resort is packed today with a crowd that is boozing, cruising, and sunning themselves poolside. LGBTQ tour operator VACAYA has stopped by to promote its cruise offerings and I recognize their bikini-clad spokesman from LA.
But I donโt stay too long. Itโs Pride Sunday and heat be damned Iโll be holding up a 100-foot Pride flag along with dozens of other volunteers and marching in through city streets. The Key West Pride parade is a modest affair and most of the folks who have gathered to watch it queue up along Duval Street. They are why Iโm here. The best reason to march in a Pride parade is to see the faces of the people who come out to show their support, and today they include young families, energetic seniors, drunken tourists, shopkeepers, and even a โFlorida manโ or two.
Key Lime Pie (Photo by Viennetta)
Many people gather afterward for a tea dance at La Te Daโa Pride tradition. But marching leaves me famished so I instead head to Pepeโs Cafรฉ (806 Caroline St. Tel. 305-294-7192. pepeskeywest.com) on the waterfront for a sunset meal with ocean breezes. Pepeโs opened in 1909 which makes it the oldest restaurant in the Keys, and it has the worn edges to prove it. Every table and chair in the joint wobbles and every piece of art could use a good level, though I dig the vintage merry-go-round horse dangling from the ceiling in mid-gallop. Servers move slow, but mine sure is a cutie. I slurp down a half dozen oysters and power through chicken Florentine served with green beans and corn on-the-cob in supporting roles. I would prefer a thicker crust-to-filling ratio in my Key lime pie, but that doesnโt stop me from nibbling around the edges of it and savoring every bite before stuffing the entire last piece in my mouth and letting the graham cracker, creamy filling, and whip cream swirl together.
As sunset washes over the city, fiery shades of pink, orange, and purple illuminate the clapboard homes, including their colorful shutters, white picket fences, and shoulder-to-shoulder Pride and USA flags. Key West really is a magical place, and itโs unfortunate for most of us that at some point we must leave the island and go back to being a respectable person again. Truth be told, I donโt know if I can.
