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Get to know Key West

Key West is a strip of paradise with the Caribbean Sea on one side and the Gulf of Mexico on the other. It’s the extreme south of South Florida, but it sometimes feels as if it’s actually a different planet, a place where feral chickens, polydactyl cats, and tourists roam. The locals take this in stride, enjoying a life that’s all about relaxation and the clear, blue water. Key West is the last inhabited island in the Florida Keys and the southernmost city in the continental United States. While Havana is the nearest big city, Miami is certainly more convenient. The island itself is a mere 4.2 square miles, though the city limits include parts of nearby islands. It’s famously quirky, yet it’s no amusement park; the people who live there are serious about not taking things seriously.

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Key West History & Culture

The origins of Key West are shrouded in mystery, starting with mysterious piles of bones, tales of ship salvagers and pirates (and the accompanying ghosts), claims by several countries, and the 1982 attempt to secede from the U.S. and form the Conch Republic. While the popular history is full of debauchery, it’s also full of artistry, with famous novelists from Hemingway to Tennessee Williams to Judy Blume calling it home—though Jimmy Buffett doesn’t anymore. Key West hosts festivals (what might more accurately be called island-wide parties) bi-weekly, but it is also home to literary conventions, fishing tournaments, footraces, and film festivals. However, most of the recreation happens on the water in fishing boats, kayaks, and paddleboards — or underneath it, where snorkeling and scuba diving is some of the best in the world.

Key West Dining & Shopping

For shopping, you can get your fill of touristy trinkets and souvenir mugs at the stores that cater to the cruise ship crowd, but Key West is also an excellent option for finding authentic Florida coastal decor. Fashion boutiques source from the world over and provide the big labels and au courant styles to the social side of Key West. Old Town Key West is the quaint and touristy section of town, where you’ll find restaurants serving up seafood and fast Cuban-inspired cuisine. And daiquiris, lots of daiquiris: Duval Street is the main strip here, and almost everyone on that mile-long tour seems to be enjoying a day-drinking kind of vacation. There are also fantastic options for fine, elevated casual dining scattered all over the island. At any of them, you can’t go wrong with the catch of the day since it’s probably the catch of 15 minutes ago.