Captain Tony's Saloon

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.