Sloppy Joe's Bar

Sloppy Joe’s: A Historic Key West Bar

Sloppy Joe’s stands as a Key West tradition, offering live music, flavorful drinks, and an inviting atmosphere since 1937. Listed on the National Register of Historic Places, this iconic Key West bar has long been a gathering spot for travelers seeking an unforgettable nightlife experience. Classic cocktails pair perfectly with house favorites like the Original Sloppy Joe Sandwich, while a curated selection of souvenir T-shirts and gift cards in the retail store allow guests to take home a piece of the fun.

Hemingway Look-Alike Contest: A One-of-a-Kind Experience

For those longing to connect with literary legend Ernest Hemingway, Sloppy Joe’s hosts the annual Hemingway Look-Alike Contest each July. Aspiring “Papas” and curious onlookers gather for lively festivities, celebrating Key West’s rich cultural past and the bar’s deep historical roots. Beyond the contest, daily entertainment continues well into the night, with dancing and crowd cams capturing every moment. Whether enjoying specialty drinks or exploring decades of vibrant history, visitors quickly discover why Sloppy Joe’s remains the best party in town.