Where to Eat and Drink in Key West (for Sailors)

Every January dozens of Bay sailors trek to the southernmost tip of the U.S. for some top-notch racing on turquoise water. A few Key West Race Week veterans recently shared some of their favorite bars and restaurants, which we’ve paired with a few local attractions that will keep non-racers happy and busy, too.

Bars & Restaurants
Blue Heaven Sit outside and enjoy your meal. Pay no attention to the chickens that may wonder by your table. The food is terrific, and the mojitos are even better.
Virgilio’s An excellent bar and restaurant with crazy good martinis ranging from traditional to girlie to full-on espresso. The outdoor bar in back is open air and host to some top-notch bands.

Chesapeake sailors often congregate at Smokin Tuna, a great outdoor bar with live music that’s situated close to regatta central. Scott Kirby, one of the owners, is a regular at the Boatyard Bar & Grill in Annapolis.
La Marquesa Upscale dining with white tablecloths and seriously good food and service. Fair warning: this place is not for the sloppy post-regatta party crowd.
Kelly’s Caribbean Bar, Sloppy Joe’s, Pepe’s, and the Hog’s Breath Saloon All tried and true. You won’t go wrong with any of them.
Attractions
Sunset Celebration See the sunset over the Gulf of Mexico from the waterfront at Mallory Square. Fun-loving entertainers such as comedian-jugglers and musicians are the opening act before nature’s main attraction. 
Mel Fisher Maritime Museum Named for Florida treasure hunter Mel Fisher, includes an exhibit on the 1622 Spanish Galleon discovered in 1985.  melfisher.org
Key West Aquariumkeywestaquarium.com
Ernest Hemingway Home and Musuem:hemingwayhome.com
Butterfly and Nature Conservancy: keywestbutterfly.com
Tour and Charters
Glass bottom boats 
snorkel
scuba 
dolphin encounters
parasailing 
jet ski tours
fishing 
Key West has several outfitters. You’ll find many of them listed at: 
keywestattractions.org and 
keywestchamber.org