An inky, flooded road skirts the edge of a trailer park on Stock Island, a square-mile swath of land just east of Key West. Two men in rubber overalls stomp through the water, sheets of rain smacking their bright-orange suits. They head toward Hogfish Bar & Grill, a rickety restaurant beside the old shrimp docks. Inside, wooden picnic tables — topped with local pink shrimp, hogfish, and grouper — crowd the noisy dining room. And though the weather calls for staying home, Jimmy Buffett's voice coos from the speakers as if everything outside is sunny and warm.
From Miami, the three-hour journey is long — stretching from Homestead's nurseries to the Seven Mile Bridge to the southernmost point of the continental United States. But the Hogfish (6810 Front St., Stock Island; 305-293-4041; hogfishbar.com) is the ideal endpoint, stocked with knickknacks, straw roofs, and fresh, fried seafood. It helps that it isn't dog-eared in any Lonely Planet guide books. That, along with a trailer-dotted trek, provides a semblance of secrecy.
The best destinations always feel like discoveries of your own.
Hogfish Bar and Grill
Key West still boasts this arcane charm, and it easily transforms vacationers into residents. Fringed by ramshackle conch houses and loud roosters, the city hooks you. Saunter down Duval Street and nobody will pester you with flyers or lobster deals. Sure, there will be bachelor parties, neon T-shirts, and the occasional fanny-pack-clad grandparent. But along the way, there will also be Apalachicola oysters, Key West Sunset ales, and enough conch fritters to necessitate a dose of Crestor.
Still, despite its perch by the sea, finding local fish can prove difficult. For years, the island's seafood industry has declined. The rise of fuel prices and imported, farm-raised seafood has forced local fishermen out of business. According to Florida Keys Weekly, there are only three local commercial shrimpers left in the Keys — a staggering decline from the 200 boats in the 1970s.
If you know where to look, though, you can still find what you want.
Waterfront dining is a big part of the island's appeal. At the Half Shell Raw Bar (231 Margaret St., Key West; 305-294-7496; halfshellrawbar.com), a restaurant immortalized on the cover of Kenny Chesney's single "When I See This Bar," you can chill on wooden benches with a marina view. Surrounded by vintage license plates, the bar hosts happy hour with two-buck Coronas and a dozen Gulf Coast oysters for $6. When in season, jumbo stone crabs are served on ice with lemon wedges and key lime mustard.
Best of all, around sunset, boats leave the marina for tours — and if you're lucky, you can hear the water slap against the docks as they drift away.
There has always been a hippie, bohemian side to the Keys, but until now there wasn't a taco stand-meets-juice bar. Mashing an Angeleno's palate with a local's taste for seafood, Bad Boy Burrito (1220 1/2 Simonton St., Key West; 305-292-2697; badboyburrito.com) peddles kale smoothies and tofu burritos just a block from Duval Street.
At this cramped, standing-room-only restaurant, a platinum-blond woman with bold tattoos and scarlet lips takes your order on an iPad. You'll probably go for the burritos, which are bulky and crammed with basmati rice and rattlesnake beans. Their fillings include carnitas, wild mushrooms, or steak, spiked with sauces like spicy mango habanero and red chili. Don't be afraid to get messy. Here, everything is served with biodegradable napkins.
Key West pink shrimp tacos ($9) — handmade corn tortillas crowned with grilled shrimp, jalapeño, radishes, and sour cream — are probably best when ordered to-go. You can enjoy them at Smathers Beach, a half-mile expanse where waters are calm and shallow, and paddleboards rent for just $20 an hour. Splashed with pico de gallo and verde sauce, Bad Boy's fish tacos are stuffed with local catches such as hogfish or snapper. They pair well with a watermelon agua fresca ($5) and especially well with toes wiggling in the sand.
Bad Boy might remind you of Miami's My Ceviche, but you'd be hard-pressed to find a local version of Glazed Donuts (420 Eaton St., Key West; 305-294-9142; glazeddonutskw.com). Located near Mallory Square, the barely decorated doughnut shop offers a dozen flavors per day. Sweetened with Florida fruits, varieties include candied kumquat, blood orange marmalade, and key lime pie. Packed with a tart custard, the last is dolloped with toasted meringue and ground graham crackers. It might not be an ideal breakfast, but it surely qualifies as dessert.
Glazed Donuts also offers organic coffees, sloshed with scalded milk in café con leche. Try it with the maple bourbon and Canadian bacon doughnut — it's a pairing any true Miamian would approve of.
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When it's time for classics, though, there's still no place better than the Hogfish and its old Keys feel. Though it's usually available, hogfish is a tough catch and must be spear-caught by divers off coral reefs. You might want to indulge in the hogfish sandwich ($14.95), smothered in Swiss cheese, mushrooms, and onions. But you must also try this white-fleshed fish in its purest form — grilled — when its flavor comes through clean, pure, and as smooth as perfectly cooked scallops.
The peel 'n' eat pinks are equally important. Remember: At the Hogfish, you're overlooking what was once Key West's cardinal shrimp fleet.