5 Best Restaurants in The Florida Keys, Florida

The outdoor dining area here is often referred to as "the quintessential Keys experience," and it's hard to argue. There's much to like about this historic Caribbean-style restaurant where Hemingway refereed boxing matches and customers cheered for cockfights. Although these events are no more, the free-roaming chickens and cats add that "what-a-hoot" factor. Nightly specials include black bean soup, Caribbean barbecue shrimp, and jerk chicken. Desserts and breads are baked on the premises.

While local anglers gather here for breakfast, lunch and dinner bring a mix of islanders and visitors for straightforward food and front-row seats to the sunset. Live music seven nights a week ensures a lively nighttime scene, and the menu staves off inebriation with burgers, barbecued baby back ribs, and Parmesan-crusted snapper. Key lime pie comes frozen with mango sauce. Service can be less than stellar and the gathering at sunset is always crowded.

A few yards from Florida Bay, this popular seafood restaurant, completely renovated in 2023, has large picture windows that offer great sunset views, though most patrons dine outside on the sand. The menu includes such irresistible entrées as lobster linguini and a prime rib eye. In addition, there are sandwiches, a burger, and sushi. And you can't miss the restaurant's famous Key lime pie and seasonal fruit crisp. The extensive property has two tiki bars and a boutique.

Sister restaurant to Blue Heaven, this colorful establishment sits on Higgs Beach, giving it one of the island's best lunch views—and a bit of sand and salt spray on a windy day. The intriguing menu is Italian with a Caribbean flair and will not disappoint. For dinner, popular dishes include linguine with mussels, lasagna, and white bean soup. At lunch the gazpacho refreshes and the yellowtail sandwich will having you singing "Amore."