There’s more to continental America’s southernmost destination than its famed, boozy main drag, Duval Crawl. In addition to fun in the sun, there’s an abundance of fresh seafood, a spunky arts scene and spectacular sipping far and beyond the isle’s Margaritaville reputation.
Were he still alive, the rum-loving Ernest Hemingway might be a regular at the tasting bar of Paul Menta’s Key West First Legal Rum Distillery. Florida cane sugar provides the backbone for the 10 rums made in this former Coca-Cola bottling plant. (Can’t tote those bottles? The distillery will ship them.) Mark Gambuzza’s Uva Wine Shoppe offers 200-plus biodynamic, small-production bottles for sale. There’s also a chill wine bar, where pleasurable pours complement cheese and charcuterie. Across the street, well-appointed gents will appreciate the fine linen shirts at Assortment, but it’s the nautical-themed, hand-embroidered Smathers & Branson flasks, key chains and belts that will serve as a lovely reminder of your balmy break from reality.
Key West is known as a world-class fishing haven. It also offers abundant fresh produce and Latin-flecked culinary influences. Indulge in oysters at the Thirsty Mermaid on Fleming Street. Alternatively, the green gazpacho with a Key West pink-shrimp centerpiece is a tangy kick-off to the locally sourced seafood menu. Grab a seat at a hot-pink ironing board-turned-table at Pescado food truck, stationed in the Chevron parking lot on Truman Avenue. It serves up outstanding fresh seafood sandwiches, bacon-jam-slathered burgers and tamarind iced tea. At Bien Key West, nab a succulent slow-roasted pork shoulder sandwich smothered with sweet sautéed onions and creamy aioli.
If you’re craving pizza, Onlywood tops its Neapolitan-style pies with house-made mozzarella, then cooks them in a wood-fired oven.
For $10 a day, nab a coaster bike from We Cycle on Southard Street. From there, head southwest to the bike paths at Civil War-era Fort Zachary Taylor and ride among the wild, 54-acre grounds that rim the beach. Pedal back up to Margaret Street and visit the historic Key West Cemetery. Points of interest include the resting place of barman “Sloppy” Joe Russell, as well as the city’s famed hypochondriac, B.P. “Pearl” Roberts, whose epitaph reads, “I told you I was sick.”
Watch anglers cast for snapper at the White Street Fishing Pier, or relax amid the rare tropical plants, cascading orchids and shady palms at the Key West Garden Club. If performances are your thing, book tickets at the recently renovated Key West Theater, which hosts national acts like Alan Cumming and Grammy-winner Marc Cohn. And be sure to stop in for a rollicking nightcap beneath the parachute-strewn ceiling at the classic Green Parrot Bar, where most nights of the week you’ll hear great live music in genres ranging from rockabilly to Delta blues.
Avoid the plastic cups of Duval Street for proper craft cocktails at 2¢ on blink-and-miss-it Applerouth Lane. Try the “Oh Captain, My Captain,” a tasty tropical storm of Flor de Caña rum, house-made ginger shrub, fresh lime juice and coconut water. The bar at the Orchid Key Inn is steps off Duval, but its tucked-away feel and giant jar of fresh pineapple-infused vodka makes for a civilized respite. On Caroline Street, in the back of craft-beer spot The Porch, is Caroline’s Other Side, whose boutique size belies its multitude of whisk(e)y options, among other rarefied spirits.
Jimmy Buffett made Key West synonymous with his signature anthem “Margaritaville,” and you shouldn’t miss the salt-rimmed version at Pepe’s, where bartenders squeeze limes in a giant juicer. Don’t skip the sunset views and excellent Hemingway Daiquiri at Hot Tin Roof, named for Key West’s other literary regular, Tennessee Williams.
4 Hour Getaway
The surrounding waters have an indelible influence on Key West, so cruising its pretty perimeter is a must. Cool Key West offers a 28-mile jet-ski tour with stops at beautiful mangroves, the Sambo coral reef and the Southernmost Point. Book at least two weeks in advance and be ready to work up an appetite (jet-skiing is hard work). The fresh seafood at Louie’s Backyard is a perennial fave.
Last Updated: May 4, 2023