Captain Tony's Saloon

428 Greene St, Key West, FL 33040


Captain Tony's Saloon, the oldest bar in Florida and the original home of Sloppy Joe's, is steeped in history, having once been an icehouse, a morgue, a wireless telegraph station, a cigar factory, and a bordello, before becoming the famous watering hole it is today. Built in 1851, the saloon has seen many changes, becoming a gathering spot for legends such as Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein, and Jimmy Buffett. Its namesake, the late Captain Tony, a fishing boat captain, gunrunner, casino operator, and former Mayor of Key West, was renowned for his larger-than-life character. Many have likened him to a character straight from a Hemingway novel. The saloon has endured various transformations and name changes over the decades, from the Duval Club in the late-Victorian era to the Blind Pig, a speakeasy that specialized in gambling, women, and bootleg rum. In 1933, it became Sloppy Joe's Bar, thanks to Joe 'Josie' Russell, a friend of Ernest Hemingway's. In the 1970s, Jimmy Buffett launched his career here, often getting paid in tequila. Today, the saloon remains a beloved part of Key West's history and culture, preserving its past while providing a lively atmosphere for locals and tourists alike. Despite the modern changes, the spirit of Captain Tony's Saloon lives on, making it a "must visit" for many returning visitors.

Upcoming Entertainment

Gabriel Wright

May 25, 2024 - noon

Gabriel Wright

May 27, 2024 - 4:30 p.m.

Gabriel Wright

May 29, 2024 - 4:30 p.m.