- Once an icehouse, this lively spot is one of the city's most popular bars and is said to have been the original Sloppy Joe's, entertaining author Ernest Hemingway. Jimmy Buffet sang here for a while in the beginning of his career and now live bands play nightly, who knows, perhaps you will hear the next Buffet. Stop by for a drink, or just to take a look at the "Hanging Tree," located inside the bar.
Captain Tony Tarracino, who died Nov. 1 at age 92, came to Key West from New Jersey in 1948 with $18 in his pocket. Ten years later he purchased the bar on Greene Street and changed its name to Captain Tony's Saloon.
A former charter boat captain, gambler and reputed gunrunner, Tarracino served as mayor of Key West from 1989 to 1991. Though he sold his bar in 1989, he remained a public figure who often stopped by to greet patrons.
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