The building housing Captain Tony's Saloon has a history as colorful as the town of Key West itself. When first constructed in 1852, 428 Greene Street was an ice house that doubled as the city morgue. In the 1890s, it housed a wireless telegraph station. The telegraph's most important utilization came in 1898, during the Spanish–American War. The battleship Maine was destroyed, as the news came from Havana to Key West and it was reported all over the world from this building.In 1912, the building was home to a cigar factory. Later, it was a bordello and a bar popular with the Navy until it was forced out of business. After that, it became several speakeasies, the last of which was named The Blind Pig, specializing in gambling, women, and bootleg rum.
By the 1930s, a local named Josie Russell bought the business and created Sloppy Joe's Bar. This was where Ernest Hemingway spent most of his evenings between 1933 and 1937. In 1938, when the building's landlord raised the rent one dollar per week, Russell and his customers picked up the entire bar and moved everything to Sloppy Joe's current location at 201 Duval Street. The bar then went through several iterations until 1958, when Captain Tony Tarracino, a local charter boat captain, purchased the bar and named it Captain Tony's Saloon. As Captain Tony's, the bar is where Jimmy Buffett got his start in Key West. Buffett played Capt. Tony's in the early '70s, and was often paid in tequila. Buffett immortalized the bar, & Tarracino himself, in his song "Last Mango in Paris". On occasion, Jimmy will make surprise appearances at the bar, but only performs at his own place around the corner called Margaritaville Cafe.
Tarracino sold the bar in 1989, but continued to appear there most Thursdays to greet customers and fans until his death in November 2008.