An archipelago born of an ancient coral reef, cut off from the country until Henry Flagler’s railroad famously braved the hurricanes and humidity in 1912, the Florida Keys skip and jump across aquamarine waters for 127 miles between Miami and Key West. Long associated with drunk escapists and serious fishing (thank you, Jimmy Buffett and Ernest Hemingway), the islands have grown more family-friendly over the years, but you still need not travel far to find a boisterous bar bedecked in bras and far-flung license plates, patronized by some bizarre combination of bikers, fishermen, drag queens, and sunburned tourists.

But it’s not all kitsch and sea views: There’s a distinct island culture at play here, an anything-goes liberalness and unhurried serenity that feels far, far away from mainland America. Even in quirky, rowdy Key West, you can walk a block or two from the action and find yourself on a mellow side street, where Caribbean music wafts from old wooden houses and roosters wander the bougainvillea. The easygoing mind-set extends to the culinary realm as well: The best restaurants in the Keys tend to be no-frills, picnic-table affairs where the day’s local catch determines the menu and preparations are simple, or family-operated Cuban restaurants dishing cheap, authentic fare well off the main drag. Slip on your flip-flops and prepare to consume a whole lot of seafood, key lime pie, and, well, margaritas. Legends die hard down here.

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