Rick's Bar

10 Best Bars in Key West | Condé Nast Traveler

"Rick's eight-bars-in-one concept is more of an entertainment complex than a straight-up bar. Rick's, the flagship, is a typical tavern with late-night karaoke; Durty Harry's is a live rock music venue with a beer-and-shots sports-pub vibe. Rick's Loft goes the swanky cocktail bar route, while Rick's Tree Bar—a rooftop venue—does fruity cocktails with bird's-eye views of Duval Street below. You could come here every night of the week and have a totally different experience. Of course, there are quieter and more intimate venues in the whole of Key West (not to mention, wilder ones), but that's not why you're here. It's a good fit for a larger group: think, a guys' weekend or a bachelorette party." - Jennifer M. Wood