Photography by Kaylinn Gilstrap
You can tell a lot about a place by its bars. Some neighborhoods are as stiff as their martinis; others as homey as their strung lights. On the surface, Key West—that four-by-one-mile sliver of sand at the southernmost part of the United States—seems to follow the same formula: Its bars certainly mirror the larger-than-life personalities (Hemingway, Buffett) who clustered about the island like metal filings to a magnet. But that, of course, is to miss the point entirely. When you find your place in Key West, whether it’s a full-scale Lisa Frank–esque immersion or a dingy, rum-soaked dive, you understand why people seek this place out: No matter who you are, there’s a seat waiting for you at the bar. You just have to find it.
Photography by Kaylinn Gilstrap
The Roost
Maria Sharpe wanted to create something that didn’t exist in Key West: A bar where your elbows don’t stick to the tables and where craft cocktails flow alongside caviar, crème fraîche, and blue-cut salmon. “I basically designed a bar for myself,” she says. It took a bit of imagination—the narrow Fleming Street storefront, once a liquor store named Baby Cheapee’s, was choked with dust and grime when Sharpe bought it in 2015. Two years later, she’d transformed it into a cozy, calming space with blue walls and local art. At just 20 seats, it’s a fairly intimate spot, a neighborhood bar that feels worlds away from raucous Duval Street, just half a block away. And though Sharpe still holds that liquor license—be sure to peruse the well-stocked mahogany “liquor store” lining the west wall—the vision for this clandestine “captain’s quarters” is all her own.
Photography by Kaylinn Gilstrap
You’re ordering: Mariarita: “It’s named for me because I like my drinks spicy,” Sharpe says. A twist on a traditional marg, it’s spiked with housemade habanero syrup.
Stop and smell the rosé: Any time is a fine time to post up at the Roost’s street-facing tables—but the bar’s Saturday afternoon wine tastings have developed a cult following; book your tickets online well ahead of time.
Photography by Kaylinn Gilstrap
22&Co
Drag bar 22&Co is nothing if not eclectic. Or, as bartender Tom Flip puts it, “an aesthetic fusion of Pee-Wee’s Playhouse meets [whimsical designer] Lisa Frank.” This drag bar, named for the tutus (“2-2” is a play on “tutu”) ringing its 15-odd barstools, operates in a different sphere than the neon-hued watering holes it neighbors. Here, a weirdness, a funkiness, a fun-ness suffuses the air. Here, because of its deep ties to the LGBTQ and drag communities, 22&Co has the distinction of being among the city’s most welcoming drinking establishments. And here, bartenders include a marine who paints his toenails and a number of born-and-bred Conchs (aka Key West natives). “We’re so small that we can get away with being the weird kid on the block,” Flip says. “And we lean into it.”
Photography by Kaylinn Gilstrap
You’re ordering: Espresso martinis might outsell peanut-butter martinis at 22&Co, but Flip says the delectable, Reese’s-cup-in-a-glass is what gets people in the door.
Sunday funday: If you’ve never passed a Sunday afternoon sipping glitter-spiked cocktails while a legend-among-legends drag queen named QMitch calls out Bingo numbers . . . now’s your chance.
Photography by Kaylinn Gilstrap
Sloppy Joe’s
Hemingway is hard to miss at Sloppy Joe’s. He peers out from the walls, from a blown-up 1952 Life magazine cover, from dozens of framed archival images. And he’s certainly visible come July when the bar hosts the four-decades-long-and-counting Hemingway Lookalike contest (the winners of which earn a place on Papa’s Wall). But while the legendary writer and adventurer might be the bar’s claim to fame (he helped name the place and based To Have and Have Not’s protagonist on the bar’s original owner), there’s more to Sloppy Joe’s than Papa Hemingway. Get longtime bartender Lou Gammell talking, and he’ll spin a yarn or two, not just about the bar’s legendary history, but about its present: He’ll tell you that live music fills the air from noon to 2 a.m. every day of the year. That legends pay their own brand of tribute here (Kenny Chesney has been known to drop in for surprise acoustic sets). That older generations are passing along their love of this place to their grown children. It’s not just where the day ends, but where the sun also rises.
Take a back seat: For a slightly more refined experience, head to the back, where the more intimate Joe’s Tap Room offers a quieter “Clean, Well-Lighted Place.”
Photography by Kaylinn Gilstrap
You’re ordering: Papa Dobles. Although legend holds that Hemingway once drank 17 of these double daiquiris in a single evening, there’s no shame in drinking just one. Or two. Or three.
Photography by Kaylinn Gilstrap
Captain Tony’s Saloon
In 1985, Key West legend Tony Tarancino and his high-soaring tales were immortalized in Jimmy Buffett’s “Last Mango in Paris.” (“He said I ate the last mango in Paris / Took the last plane out of Saigon / Took the first fast boat to China / And Jimmy there’s still so much to be done”). Not that he—or his eponymous establishment, housed in a former icehouse-slash-makeshift-morgue—needed much embellishment. Because at Capt. Tony’s Saloon, there are nothing if not stories, about ghosts, unrivaled nights of revelry (as the long lines of women’s brassieres suggest), and the rakish owner himself (RIP), all tangling about the place like seaweed. Those interested in the history should visit during the off-hours (say, Sunday mornings, when many patrons are sleeping off their hangovers). Those wanting to become part of the place, however, should pay their respects on a weekend night—just know that stories tend to blur with a glass of Pirate’s Punch.
Share a seat: Saddle up at one of the stools known for the celebrity it used to support—think Dan Marino, Shel Silverstein, or Sean Connery. Sadly, you won’t find Jimmy Buffett’s on the ground; his chair is suspended above the pool tables, along with those favored by Truman Capote and JFK.
Photography by Kaylinn Gilstrap
You’re ordering: The quintessential (for better or worse) Key West beverage: Pirate’s Punch, the saloon’s signature rum punch.
Photography by Kaylinn Gilstrap
Lagerheads Beach Bar & Watersports
Lagerheads Beach Bar & Watersports might not be terribly off the beaten path—but it’s certainly where the sidewalk ends. Sandwiched between two larger resorts on a small strip of white sand at the end of Simonton Street (not for nothing, the address is “0”), Lagerheads is the only bar in town where you can order a drink to-go from the open-air counter—and then wade into the ocean with it. What’s more, it also has a serious Key West pedigree: One of the owners, Josie Magrath, is the youngest daughter of Tony Tarracino—he of Capt. Tony’s Saloon fame (and infamy). Although there’s certainly nothing wrong with posting up on nearby Duval, Lagerheads’ sandy footprint and laid-back vibes—to say nothing of its boozy boat tours—offers patrons a compelling reason to chart a different course. “It’s this little nook,” longtime bartender Rose Chambliss says. “This little tiny beach no one knows about.”
Just row with it: Although the adjacent resorts are your best bet for watersports (kayak, paddleboard, etc.), Lagerheads operates six- and 16-seat rum runner expeditions around the island (book online).
Photography by Kaylinn Gilstrap
You’re eating: This is a bar whose fare goes far beyond peanuts. Spring for the conch ceviche and fish tacos topped with mango salsa.
Photography by Kaylinn Gilstrap
Green Parrot
The walls might talk a good bit at the Green Parrot, but the ceiling has just as much to say. Faded photographs, sun-kissed bar signs, out-of-state license plates, and various visual ephemera cover every flat surface. This can make standing in the 1890s-era-grocery-store-turned-WWII-era-Navy-bar-turned-funky-open-air-dive-bar a little overwhelming. And yet, to hear the Fossums—Dani and Jim, who’ve been behind the stick for many decades—tell it, what adorns the walls gives the Parrot a status that transcends “watering hole” and “museum” alike. It’s not only a history of the island as told by, say, a marooned Hobie Cat mast or a weather-worn parachute above the bar (just ask), but a place where so many locals, musicians, and even out-of-towners have found a home away from home, becoming characters in the story preserved all around them.
Listen in: Not unlike its eclectic decor, the Parrots boasts a far-flung blend of funk, reggae, and rock from across the state, region, and country. What’s consistent? There’s never a cover.
Photography by Kaylinn Gilstrap
You’re ordering: Toast the Green Parrot’s past life as a schnapps bar (yes, really), and order the root beer barrel shot.
Photography by Kaylinn Gilstrap
General Horseplay
Casting a glow over the open-air space behind General Horseplay, a large lightbulb marquee reads “Why Not?” Undoubtedly, there’s a skosh of devil-may-care-ness in this establishment carried over from nearby Duval Street. And yet the vibe inside is less horseplay, more refined, with heavy red curtains and a pressed-tin ceiling, oozing New Orleans cool, not Florida Keys chill. “I prefer to think of it as a mullet bar,” co-owner Tim Rabior says. “Business in the front, party in the back.” Although the bar doesn’t take itself too seriously, as its tagline of “tomfoolery and cocktails” suggests, the cocktail program is certainly not kidding around. Because there aren’t many other bars on the island serving up high(est)-end cocktails with 18-year-old Yamazaki Japanese Whisky or Jameson Bow Street 18 Cask Strength. (At $150 and $50, respectively, these drinks fall under the menu’s Why Not? heading.)
Photography by Kaylinn Gilstrap
You’re ordering: Go for the Creme Bru-lime, made with house-made clarified Key lime vodka, Key lime pie liqueur, and torched meringue. Stay for the bar’s Instagrammable take on an old fashioned, the Smoke & ‘Choke.
You’re DIY-ing: Up your Old Fashioned game with a two-hour, three-cocktail crash course on shaking up the classic cocktail with one of General Horseplay’s mixologists.
Photography by Kaylinn Gilstrap
Chart Room Bar
Chart Room is a time capsule. Or maybe it’s closer to “a complete contradiction,” as bartender Rob Palamountain describes it. Housed in the upscale Pier House Resort, this one-time cinder-block motel room doesn’t exactly mesh with its posh environs. The nautical charts push-pinned into the ceiling came from one-time regular and Key West treasure hunter Mel Fisher, who often bellied up to the bar with his good friend Jimmy Buffett. What’s kept the place in proverbial amber is the stuff of legend as well: Palamountain says the ashes of longtime regulars Panama Peat, Bob, Whistle Pants, and Fisher, corked in the wood of the bar, have kept the place from getting tampered with, as per Florida law. Although the place does indeed get hopping—“you put 35 people in a bedroom, it’s going to be raucous,” Palamountain says—there is something that feels truly transportive about Chart Room. And sometimes that place, well removed from Duval, is exactly the place you want to be.
You’re ordering: A bottle of Heineken, the first “on-the-house” beer that Jimmy Buffett reportedly received from the bar in exchange for playing tunes.
Photography by Kaylinn Gilstrap
Feeling munchy (and brave)?: Snag a hot dog from the ancient crockpot. Locals have been known to take shots of the hot-dog water with dried mustard dusted around the rim. It’s said to have mixed reviews.
This article appears in the Winter 2025 issue of Southbound.
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