Nowhere has made a virtue of being out on a limb like Key West. At the end of the Florida Keys island chain, and a four-hour drive over spectacular bridges from Miami, it’s not somewhere you stumble across accidentally.
Those who make it to Key West really want to be there, and this feeds an air of utterly compelling woozy eccentricity. You can never quite be sure whether the swaying man in a Hawaiian shirt and flip-flops is a hobo or a billionaire letting it all hang loose.
Around this vibe of often-surreal silliness is a heritage of shipwrecks, pirates and Ernest Hemingway debauchery. If Disney repositioned itself for adults, Key West is possibly what it’d come up with.