Hit the Highlights During a Weekend in Key West

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Because Key West, Florida is so close by plane, it’s a great weekend getaway destination. And even though most weekend trips are only a few days long, that’s still plenty of time to pack in lots of fun and excitement in Key West. From great food to dynamic excursions, guests of Key West are sure to have an exciting experience any time of year. 

Best Places to Eat

Key West has long been home to people from all over the world who have brought their own cuisines and influences. Among the Key West institutions is Duetto’s Pizza and Gelato, serving hand-stretched pizza with authentic Italian flavors. You can choose to dine in or take your pizza to go–just don’t forget to get a scoop (or several!) of homemade gelato, too. At Kermit’s Key West Key Lime Shoppe, you can try the city’s signature dessert, key lime pie. The folks at Kermit’s bake it fresh every day, and there’s a charming koi pond on the grounds so you can sit outside and enjoy a slice without delay. Kermit’s also has a full cafe menu, making it a great spot for a light meal, too. Shop their shelves of jellies, relishes, chutneys, sauces, and candies for treats to bring home for yourself and others.

At Eaton Street Seafood Market and Restaurant, you’ll find fresh fish you can buy to prepare in your own kitchen or select menu items to enjoy al fresco. Shady tables welcome guests who’d like to  linger over lobster roll, fried fish baskets, stone crabs, crab cakes, and more. And if you can’t do without that Key West seafood, Eaton Street Seafood Market and Restaurant also ships fish, shellfish, and lobster around the country, directly to you.

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If you can’t get enough seafood, stop at the Seaside Cafe and Bar, located at the Southernmost House Mansion. Seaside tables provide diners with amazing views while you enjoy creative seafood and pizza dishes with local flair. There’s also a great frozen drink menu to make it feel like a tropical vacation, plus champagne and wine selections, too.

Best Things to Do

If you have time to wander Key West, the cigar shopping is worth a trip. Rodriguez Cigar Factory is the oldest one in the city, founded in Cuba nearly a century ago. Made with leaves from Ecuador, Nicaragua, and Honduras, the cigars are known for their high quality. Tour the cigar-making facilities and learn more about the art of rolling cigars, and try your hand at it, too. Or relax at Nailtini Day Spa. Guests enjoy complimentary martinis, wine and soft drinks during their treatment. Book manicures, pedicures, facials, and several massage types, including Swedish and deep tissue. Walk up and down Duval Street for more shops, galleries, cafes, and bars to explore.

Best Adventures

One of the most popular activities in Key West is booking a charter fishing trip. Take a day or half-day and head out into the open water for the chance to catch your own tarpon, grouper, and more. The great thing about a chartered fishing trip is that all you need to do is show up with lunch and sunscreen. The captain and crew take care of your permits and licenses, fishing gear, and other supplies. For more sea adventures, go on a sunset cruise around Key West. You’ll get to view the highlights of the island from a unique vantage point while enjoying light snacks and wine or cocktails as the informed and engaging crew share their insights about Key West, its history, and its people. Take your tour of Key West to the next level by booking a helicopter tour. In just about ten minutes, you’ll cover 20 miles of geography, history, and culture from your seat high above the island. If independent exploring is more your speed, book a self-guided tour using a kayak, Jeep, paddleboard, or bike. Adventure tour companies have pre-planned tour routes you can follow or you can embark on your own.

Best Historical and Cultural Spots

If the roads of Key West could talk, they’d have tales of presidents, writers, and explorers to share. The Little White House, where President Harry S. Truman often vacationed during his presidency and where he welcomed diplomats, military leaders, and others involved in key decisions on international relations, is open for tours. The home still has many of the building’s original furnishings plus presidential memorabilia. The U.S. Coast Guard Cutter Ingham now functions as a maritime museum. Exhibits showcase the ship’s time at sea around the world and throughout several military conflicts. At the Mel Fisher Maritime Museum, you can see the artifacts retrieved from area shipwrecks and learn about the science that goes into salvaging ships and their treasures. 

Key West provides visitors with lots of opportunities to enjoy sights, sounds, and tastes that are unlike those found anywhere else. Even with just a few days, you’ll find there’s plenty to explore, from restaurants to shops, museums, and historical sites. Plan your itinerary in advance, and you’ll be able to begin your adventures upon arrival.