Foodie Road Trip: Florida Keys by the Bite

Locals’ Favorite 

As fresh as catching it yourself but with no deep-sea fishing charter required, the Fish House in Key Largo is a family-owned spot that’s been open (and adored) since 1982. It’s one of the few remaining establishments that purchases only from local commercial fishermen and fillets everything on the premises. Order the fresh catch prepared in their signature Matecumbe style—featured on the Food Network—and prepare to be blown away by this unassuming eatery beloved by locals and visitors alike. 

Take it Home

Don’t drink and drive. Grab a can of any of 60 brews (or swag) from the source of craft beer in the Keys: Islamorada Beer Company. Their range of beers includes the well known Sandbar Sunday and even a coconut-key lime ale. The brewery and tasting room now features an onsite distillery, too.

Grab ’n’ Go 

Stopping for a fresh fruit milkshake from Robert Is Here in Homestead—all grown up from its humble 1959 beginnings as a six-year-old boy’s roadside fruit stand—is integral to the Keys experience. Still operated by Robert himself, Robert Is Here sells every kind of fruit you’ve ever heard of (and many you haven’t) as well as locally made sauces, spices, and jams. Grab a shake or freshly cut fruit to make the trip sweeter as you bid the mainland goodbye and hit the Overseas Highway. 

Bar Scene

With an unbeatable view of the famous Seven Mile Bridge and the brilliant colors of the sinking sun come sunset, Marathon’s Sunset Grille & Raw Bar is aptly named—and a longtime go-to for winding down with a tropical tipple at the end of another day in paradise.

Hot Spot 

Perhaps every visitor to Key West since 1933—when the institution, ahem, conveniently opened the very day Prohibition was repealed—has darkened the doorway of Sloppy Joe’s; it’s a non-negotiable stop on any Keys itinerary worth its salt. To order? The Original Sloppy Joe Sandwich, of course: it’s ground beef with onions, peppers, and spices.

Hidden Gem

“A nice place if you can find it” is the slogan of Big Pine Key’s No Name Pub, which is indeed off the beaten path—down a maze of residential streets and tucked away in an otherwise unremarkable neighborhood. Few places can trace nearly 100 years of history and still fly under the radar, but No Name Pub does exactly that.

Iconic Bites

Don’t leave the Keys without pleasing your palate with these must-try regional classics:

Conch fritters: Doughy and flavorful, they’re the islands in one flash-fried mouthful. 

Fresh fish: Yellowtail snapper, grouper, mahi, wahoo, and hogfish are the usual local catches; in the crustacean family, order Florida lobster or stone crab in season.

Cuban coffee: The Southernmost Point marks 90 miles to Cuba—so close you can taste it, especially with a cortadito from nearby Cuban Coffee Queen, a counter-serve spot with personality. Tip: The iconic “Greetings from Key West” mural graces the side of the stand, so snap a pic as you sip. 

Sweet Treats

Talking top key lime pies renders controversy: Tart or sweet? Whipped cream or meringue? Pastry or graham cracker crust? It’s all a matter of taste; try these in the name of research:

Mrs. Mac’s Kitchen has two Key Largo locations where you can sample a slice that may change your life. Creamy and ice-cold, its tangy zip is cut by the understated sweetness of a homemade graham-cracker crust and a hefty dollop of a Cool Whip-like topping.

 What’s better than a slice of key lime pie? A slice of key lime pie dipped in Belgian chocolate, frozen, and plunked on a stick. Indulge at Kermit’s in Key West. 

Where to Stay

The variety of accommodation types at the five-hotel collection that is the Kimpton Key West—from original Bahamian-style “conch cottages” to elegant guesthouses—isn’t the only draw of the digs. Foodies will find lots to love, too: Book a Hemingway Affair for an intimate dining experience for two to 14 people in the two-story Hemingway Suite, during which a personal chef will prepare a multi-course meal suited to guests’ tastes; for a more casual culinary detour, kick back at poolside bars with a can of Cayo Hueso, the hotel’s own brew crafted by local Waterfront Brewery and exclusively available at Kimpton Key West.