You can tell a lot about a place by its bars. Some neighborhoods are as stiff as their martinis; others as homey as their strung lights. On the surface, Key West—that four-by-one-mile sliver of sand ...

(Sammy Todd Dyess/Courtesy Sunset Pier at Ocean Key Resort & Spa) Key West is all about dressed-down fun—but you'll find a few spots for polished cocktails, too.

If finding a great bar in Key West seems daunting, it’s only because the island can feel like one never-ending bar. On seemingly every block, you’ll find chairs with waterfront views, stools within ...