The Insider's Guide to Shoreside Fun in Key West

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
Frita’s Cuban Burgers at 425 Southard Street is new to us, and we love it! The Cuban conch fritters are “Rhode Island style” complete with chorizo. The Cuban Hot Dog rivals Davis Pub’s Chesapeake Bay Retriever. The casual food truck/patio atmosphere is perfect post-racing or post-tent. Marcia, the proprietor is from Portsmouth, RI, also owns a cigar rolling company. Stop in and get to know them.

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. Don’t miss Martini Monday - $5 martinis all night long!

Better Than Sex is a dessert only restaurant that very nearly lives up to its name! Amazing drinks and dessert. We tried the Morning After and the Missionary Crisp. Amazing! 926 Simonton Street. A bit of a walk from Duvall but worth it. Be sure to make reservations 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.

Azur, the restaurant at the Eden House, just a few blocks from West Marine, serves up one of the best breakfasts in Key West. Try the eggs benedict with arugula and brie

Kelly’s Caribbean Bar,  Pepe’s, and the Hog’s Breath Saloon All tried and true. You won’t go wrong with any of them.


For the book lover in your group, be sure to swing by Key West Island Books just a block off Duvall on Fleming Street. New and used books. Loads of nautical and sailing books as well as Key West novels and classics. They even have the Ed Cutts biography – a little taste of the Chesapeake in Key West.

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.

Key West Aquarium Check out all the life that exists below the surface at the Key West Aquarium, then be sure to head over to Fort Zachary Taylor State Park to get your toes in the water!

Ernest Hemingway Home and Musuem It's great to see the place where the writer found solace (and had a few adventures, let's admit it). But if you're allergic to cats, be sure to bring along the Allerga: the grounds are covered in the progeny of Hemingway's famous six-toed kitties.

Butterfly and Nature Conservancy A short trip but still a very fun one, especially for the kiddos. Parents will find some respite here in the circus that is Key West Race Week.

Tours 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: and