Bright, fruity tipples, raucous cabaret shows, live jazz performances: by the beach, it’s all about dressed-down fun.
While frozen cocktails with tiny umbrellas (and the tiki bars that serve them) may be a relic of the 1950s in most other places, they’re still a staple of the Florida Keys. Sure, the area has evolved to suit the increasingly luxury-loving clientele who visit, but it also works hard to maintain that frozen-in-time feel (pun intended) that keeps tourists flocking to Florida’s most southerly region year after year. The Keys’ relaxed, lived-in vibe carries over to its bar scene (for the most part); having drinks with friends usually involves a pair of comfy jeans and a T-shirt, plus at least one fruity concoction, as you’ll find at the infamous Sloppy Joe’s. Sea views are, of course, optional, though encouraged (Sunset Pier and Hogfish Bar and Grill have some of the best). But if you’re looking to get dressed up and make it more of an occasion, there are plenty of venues to fit the bill, whether it’s a night of cabaret at La Te Da or handcrafted cocktails and live jazz by candlelight at the Little Room Jazz Club. Just don’t forget the sunblock. Here, we’ve rounded up the best bars in Key West, for when all that sunshine inevitably stirs up your thirst.