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Kicking Back in Key West

Follow our guide to the best food and fun in this quirky little town made famous by the likes of Buffett and Hemingway.

Key West Southernmost Point
Photographer Jennifer Davick

Land's End

In Key West, every day is an excuse for a good time. Its location seems to encourage the anything-goes attitude that pervades this leafy little town. Whether you fly here over the indigo-and-teal waterscape of reefs and islands or drive the 127-mile Overseas Highway, you’ll get the picture: Key West is the end of the American road.

Built in the 1800s on wealth salvaged from shipwrecks, Key West has always been a self-reliant renegade. When the U.S. Border Patrol blockaded the Keys’ access road to limit illegal immigrants and drugs in 1982, Key West seceded from the nation, dubbed itself the “Conch Republic,’’ and petitioned the federal government for foreign aid. (The blockade quickly dissolved.)

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