Sloppy Joe’s Bar

Sloppy Joe’s is a historic bar and restaurant at the corner of Duval and Greene in downtown Key West. Live music and its Hemingway connections make it a classic stop for the island’s bar culture. Go for the room and the story; when the band is playing, it can be hard to hold a quiet conversation.

Bands play daily, and dancing is part of the nighttime scene. The menu includes the namesake Sloppy Joe sandwich, wings, other sandwiches, Key West snacks and specialty drinks. Visitors have mixed opinions about the food, so come mainly for the atmosphere, music and history rather than a guaranteed standout meal. There’s also a shop for clothing and souvenirs.

Joe Russell opened a bar called the Blind Pig at 428 Greene Street after Prohibition ended in 1933. It became the Silver Slipper before taking its current name. The story behind the name links Ernest Hemingway to a Havana barkeeper named Jose Garcia, whose floor was often wet with melting ice. After a rent dispute, Russell moved the bar to this Duval Street corner on May 5, 1937; regulars helped carry the furnishings while keeping their drinks in hand.

Russell was Hemingway’s fishing companion, and the bar became a meeting place for Hemingway and a circle of writers and local friends. Hemingway’s belongings and papers were stored in a back room nicknamed “the Hole.” His widow Mary opened it in 1962, revealing items that included uncashed royalty checks, guns, trophies, photographs and manuscript sections.

The bar occupies the former Victoria Restaurant, built in 1917. Look for the Cuban tilework, ceiling fans, jalousie doors and long curved bar that give the room its distinctive old-Key-West feel.