Key West, the southernmost town in the continental United States, is the end of the line, the last island on an archipelago that stretches 125 miles off the tip of Florida. 

Just 90 miles from Cuba, the little island was the most populous city in Florida at the end of the 19th century, thanks to the cigar and sponge industry, and today boasts Victorian mansions, literary festivals and breathtaking sunsets, as well as boozy shenanigans on Duval Street. Once home to Ernest Hemingway, Tennessee Williams and President Harry Truman, Key West is also known for attracting eccentrics, and proudly remains a patchwork of oddballs to this day. From a real-life mermaid to a third-generation local (a.k.a. “Conch”), to a larger-than-life drag queen, these three beloved locals show us that there’s more to Key West than its seedy dive bars (though those are fun too!).

For more on Key West, see our city guide here.

Gary “Sushi” Marion
LGBT Scene on Duval

“I’m sitting next to the drag queen,” Gary Marion texts me as I walk up to the flamingo-colored 801 Bourbon Bar on Duval Street. I worry that descriptor won’t do me much good at the legendary gay hot spot, but on an early weekday evening, there’s only one dressed performer at the circular bar, and Marion’s right there beside her, sharing a joke with the bartender. 

Though he’s out of character tonight, Marion is known more commonly—especially on Duval Street—by his drag persona, Sushi, a flirty quick-witted queen who gained local fame by perching, for the past 25 years, in the giant red high-heel shoe that drops every New Year’s Eve at midnight from the second-floor balcony across the street. The pageantry of it all has led to profiles by CNN and The New York Times

For 22 years, Marion performed multiple times a week here at 801 but “semi-retired” two years ago, now operating and booking other performers for the cabaret show upstairs. (Sushi still hops in that red shoe every New Year’s Eve, though.)

Originally from Portland, Oregon, Marion drove to the opposite end of the country almost 30 years ago looking for a change. Once in town, he ran inside 801 asking, “Do you know where a gay bar is?” The bartender replied, “You’re in one, sister.” He’s been a fixture here ever since.

I follow Marion upstairs to the cabaret space and we head backstage to peruse the collection of wigs, wardrobe, heels and makeup used by the dozen or so performers (the oldest I’m told is 78). Over the years, drag performances in 801 have become an iconic part of the LGBT scene Key West is known for, and the audience has included the cast of The Real  Housewives of Orange County, Hulk and Brooke Hogan, and Nick Carter. Since everyone’s “a little weird here,” Marion says he never experienced homophobia in town, and whatever snide remark he has heard always came from tourists. He’s relieved drag has become more mainstream and lucrative for performers over the years. “Financially it’s been a blessing,” he says. 

We cross the street to visit the Bourbon Street Pub, a gay bar where Marion worked his first Key West job as a janitor cleaning the toilets, eventually convincing management to let him perform in drag as Sushi. “It quickly became the busiest night of the week,” Marion says. 

We make our way upstairs to New Orleans House, one of the last gay male-only resorts in Key West, and where Marion is lowered in the red heel from the balcony. The shoe itself, a crafty creation of plywood, rests under the covered balcony. “It was all [pub owner] Joey Schroeder’s idea,” Marion says. “It was 1996 and he asked me if I wanted to get lowered in the shoe at midnight. I said, ‘Why not?’” 

After same-sex marriage was legalized in 2015, Marion wed his partner within the shoe at midnight on that New Year’s Eve. “Now I’m the old lady in the shoe,” Marion quips. 

Back on Duval Street, Marion points to a fast-food joint and explains that “everything north of the Wendy’s is Straight Town.” So we saunter south, passing Nailtini Nail Bar & Day Spa, a trendy spot where anyone is welcome to sip on cocktails while enjoying a manicure or massage, and arrive at La Te Da, where Marion takes me upstairs to a cabaret and piano bar. The show is still an hour away, so tables are empty. “I made the curtains,” Marion whispers as we head backstage to meet one of the most well-known female impersonators in town, Christopher Peterson, who imitates everyone from Lucille Ball to Joan Rivers to Lady Gaga. “I don’t promote just me—I always mention 801 in my show,” Peterson tells me backstage, nodding to Marion. “We’re all sisters here.” 

Before we head back to 801 to catch the raucous performances, Marion makes a quick pit stop at Point5, a tapas and wine bar located on the second floor of an old classic house (with a reservation, you can find more upscale dining downstairs at Nine One Five). We nab a spot on the balcony and on the way to our table, Marion shouts, “Vicky!” and hugs the Venezuelan cook who prepares our food. As we dig into our charcuterie board, Marion tells me that after his shifts here, Vicky performs at 801. “Very talented and hardworking,” Marion whispers. 

We order espresso martinis and gaze down at the stream of pedestrians below, when suddenly restaurant patrons call out, “Sushi! Sushi!” like tweens at a One Direction concert.

Marion waves back: “Hey, girl, hey!” I remark on his apparent celebrity but he’s modest about all the attention. “I’ve been here for 27 years and get dropped in a shoe,” he shrugs. “At this point, I pretty much know everyone.”

Martin Liz
Off the Tourist Path

I easily spot Martin Liz among the throng of older Cuban men sitting in lawn chairs outside the ventanita at Riviera Coffee & Sandwich Shop, located on the more residential eastern side of the island. It’s 8:45 a.m., but according to the bespectacled owner, Freddy, this caffeinated congregation starts at 7 a.m. daily, with cafecitos, guava pastries and puffs on cigars.

Liz, who lives and grew up nearby, used to stop by for an egg sandwich on his way to high school, and has been coming here almost every morning for decades. The youngest of eight children, he has family roots in Key West that date back to the 1800s, and knows all of the abuelos here by name, gabbing with them in Spanglish. 

“People who are from here aren’t on Duval Street. There’s a whole community here that doesn’t cross White Street,” Liz tells me, explaining the de facto border between locals and tourists. Today he’s showing me some of those less touristy parts of the island. After cafecitos we drive west to Indigenous Park, a seven-acre native tree and bird park where he used to volunteer at the Key West Wildlife Center. I follow him under the shaded footpaths—the park is home to some of the oldest trees in Key West—past rescued pelicans, owls, cormorants and ibises. His face lights up when we pass a gumbo-limbo tree.

Across the street is the brick West Martello Tower, which was built as a fort in the 19th century but used today as a botanical garden full of contorted banyan trees. I trail behind Liz, maneuvering past fragrant blooms to a white shaded gazebo overlooking the turquoise waves crashing into the beach. “I come here a lot to chill,” Liz says. “I like sunshine, but not directly.” 

Afterwards we drive to Old Town to the very end of Simonton Street to a tiny patch of beach with a hut called Lagerheads, one of his favorite spots for fish tacos and buckets of beer. Liz tells me that the brunette pouring brews on tap is the co-owner and practically Key West royalty: Josie Tarracino, the daughter of the famous saloonkeeper, storyteller and mayor, Captain Tony Tarracino, who worked hard to keep the island weird and who owned Captain Tony’s Saloon, the location of a bar Hemingway used to frequent in the 1930s.

From here we head into the heart of Old Town to see where Liz and fellow Conchs defied evacuation orders and rode out Category-4 Hurricane Irma at the Studios of Key West, a former Masonic temple turned performing/studio space for artists and where author Judy Blume runs the Books & Books shop. “We camped out in the staircase,” Liz tells me as we peruse the first-floor gallery displaying artist Lisa Watson’s “Deer Human” exhibition, highlighting the endangered Key deer and using materials from local landscapes. We scurry up the infamous staircase to the third floor to see work by one of Liz’s favorites: folk artist Mario Sanchez, a Cuban-American whose wood paintings and carvings of classic Key West scenes went on to inspire generations of artists and become an iconic Key West aesthetic. 

Liz wants to show me another part of the area’s past and future. We drive over Cow Key Channel to the neighboring Stock Island, dotted with marinas, fishing boats and colorful mobile homes and a bevy of new waterfront hotels. Liz’s dad worked on Stock Island as a general contractor when he was a kid, and today Liz operates his culinary event space, Lost Kitchen Supper Club, on the Safe Harbor docks here. “It was called Stock Island because it’s where all the livestock was in Key West’s early days,” Liz explains. 

Liz takes me to a modest, single-story space called El Mocho for steaming tamales and medianoche sandwiches (roast pork, ham, mustard, Swiss cheese and pickles served on sweet bread). Before we make our way to the booth, we unexpectedly run into Liz’s cousin and her children, also here for the pressed Cuban sandwiches. “I’ve been coming here since I was a kid,” Liz says. Seems like he and his Conch family are not about to stop.

Kate Kowalski
Finding Zen on the Island

In the green neon light of Fyt Gym’s studio, Kate Kowalski lies on her mat, eyes closed, and lets out a long breath with her fellow yogis at the Sunday morning Gentle Yoga class. She blinks open an eye and whispers to me that it’s her fourth day off all year. “I’m always go, go, go,” she says, shaking her head. “I’m just so happy to start my day off like this!” 

Though the 28-year-old Kowalski is not a native Conch, she moved here from Tampa eight years ago and has become known around the island for the wild array of jobs she holds: yoga instructor here at Fyt; cheerleading coach to girls ages 3 to 18; waitress at Fat Tuesday on Duval Street; model for local shops; chalk-writing logo designer; and to top it off, mermaid at various splashy events across town. That’s how she earned her nickname, Mermaid, which I later hear people holler at her as she zips around on her scooter.

To unwind from all that, Kowalski often seeks a serene location, where we’re headed now: the outdoor terrace at Azur, a tranquil Mediterranean spot with blooming orchids, tucked five blocks away from the boozy Duval Street shenanigans. “People think all we do [in Key West] is party and play on boats,” Kowalski tells me over mimosas. “They don’t see the work.” She’s such a regular that our smiling server rattles off her order before she can: a potato pancake topped with poached eggs, Brie, prosciutto and arugula with sriracha on the side. “We still work hard and get tired like everyone else,” she says between bites. “I just have better scenery.”

On her rare days off, Kowalski spends time on the water with friends, snorkeling, scuba diving or lounging at a locals-friendly hotel pool (the Havana Cabana and The Marker Key West hotels are her favorite). The beautiful seascape around Key West has inspired her to earn her captain’s license, save up for a boat and launch an excursions business where she’ll take folks out to her favorite sandbars for yoga classes or organize snorkeling or scuba diving sessions (she’s also a certified instructor). But today, she wants to show me another one of her escapes, The Gardens Hotel, a 21-room boutique inn dating back to the 1800s, two blocks away from the Ernest Hemingway Home

She calls it “the sanctuary,” and it’s easy to see why. The namesake garden is open to the public, and a labyrinth of winding brick pathways takes us past rare orchids, black bamboo and even a koi pond. Since it’s Sunday evening, a jazz band is playing on the back veranda as guests sip on wine from the self-serve bar that accepts payment with a prepaid chip card, a surprisingly high-tech gizmo amid the crown molding and brocade curtains. Kowalski leads me past the band, tables and gazebo to a shaded nook with a blue hammock. “This,” she motions with her hand, “is where I go when I need to disconnect. I bring a glass of wine, put my phone on airplane mode and just look up,” she says, pointing to the kaleidoscope of palm fronds above. 

Our next stop is the Key West Theater for the Sunday Ramble, a weekly concert series of musicians, mostly from the Florida Keys. We meet up with Kowalski’s best friend, Derik Reay, a bearded guitar tech and one of the creators of a Key West specialty, Chicktatoes—hash-brown balls stuffed with chicken and cheese that have garnered a cult following. “You have to try them before you leave!” she says. We nab a table near the stage and spend the night singing along (loudly and out of tune) to covers of “Take Me Home, Country Roads” and “Drift Away.”

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