Part of Key West’s charm is its colorful history and quirky characters who’ve shaped the island into what it is today. Get a taste of the past at Key West’s most historic and iconic restaurants.
Pepe’s Café, 1909
Pepe’s, founded in 1909, is the oldest restaurant still operating in Key West today. Locals and visitors love it precisely for that, its Old Florida charm set in a cozy backyard on Caroline Street. But that’s not the only draw; the food is as close as it gets to Florida home cooking. Breakfast is popular here with massive omelet and French toast specials, plus hand-squeezed orange juice makes screwdrivers or mimosas incredibly refreshing. Lunch and dinnertime calls for grilled mahi sandwiches or grouper specials.
Sloppy Joe’s, 1933
Sloppy Joe’s is one of the most storied restaurants on the island. Today, it’s famous for raucous parties, live music and late nights on Duval Street. But this bar actually originated in 1933 around the corner on Green Street in a space currently occupied by Captain Tony’s Saloon. This was where Ernest Hemingway spent many evenings after fishing on his beloved boat Pilar. When owner Joe Russell moved his bar to Duval Street in 1937, Hemingway carried one of the urinals from the Green Street location back to his home on Whitehead Street and turned it into a fountain, which you can still see on a tour of the home. Today, Sloppy Joe’s is a great spot for lunch with live music. And for even more entertainment, catch the annual Hemingway lookalike contest every January.
A&B Lobster House, 1947
One of Key West’s top fine dining restaurants is also one of the most historic. A&B Lobster House looks out on the Historic Seaport from a second floor perch with a lovely balcony. A white tablecloth establishment, diners love A&B for steak, lobster, fresh caught seafood, a spectacular wine list and perfectly mixed martinis.
Two Friends Patio Restaurant, 1967
Founded in 1967, Two Friends Patio Restaurant is a casual, family-owned open-air spot on a sprawling patio on Front Street. The mood is relaxed and easygoing in a location where you can watch the world pass by on the sidewalk outside. Two Friends serves fresh seafood, like local shrimp, fish, lobster, oysters, conch and crab. They also have a great menu of steaks and delicious frozen drinks to wash it all down.
Louie’s Backyard, 1971
Louie’s Backyard is another classic Key West restaurant with some of the best food on the island and one of the loveliest settings. Off the beaten path on the Atlantic Ocean side, Louie’s is set in a historic Victorian mansion with a beautiful tiered deck leading down to the water. The menu at Louie’s is a creative, upscale twist on Floribbean fare, like miso-glazed yellowfin tuna or grilled swordfish with olives and fennel salad. Come for sunset cocktails at the After Deck bar on the water or try the Upper Deck upstairs for lighter tapas-style fare.
