Captain Tony’s Saloon has been one of the top things to do in Key West for many generations. It has a rich history that stretches far beyond the time that it was called Captain Tony’s Saloon. The current location of the establishment is not the original, and the intent of the bar has changed drastically as well. The first address for Captain Tony’s was at 428 Greene Street prior to its current location at 201 Duval Street. The journey that led the original building from an ice house to Captain Tony’s is intriguing enough to draw in the crowds every season throughout the year.
The ice house became a cigar factory and then a bordello moved in. The bordello also housed a bar where people could come for a good drink and a good time. During prohibition, the bordello became a speakeasy where people could still get their hands on a good, yet illegal, drink. Prohibition was lifted and the establishment became a bar again. The 1930’s brought along Josie Russell and a new bar called Sloppy Joe’s. Unfortunately, the landlord decided to raise the rent by one dollar in 1938 and Josie was not willing to pay the price.
The owner of the establishment and his many loyal customers literally picked up the bar and moved it to the Duval Street address. By 1958, Captain Tony Tarracino decided to buy the bar and renamed it Captain Tony’s Saloon. It became known as a place where famous people sat and had drinks, sometimes performing for the crowd. Jimmy Buffett became a regular and got his start at Tony’s. He often played for the crowd and rather than cash payments, he sometimes received tequila. Buffett still shows up at the bar every now and then, but he only performs in his own bar now. Margaritaville Café is located just around the corner from Captain Tony’s Saloon.
Ernest Hemingway spent many evenings at Captain Tony’s between 1933 and 1937, and it is likely that people visiting the area will see his name along with Buffett’s and several other famous figures tagged onto the stools that they sat on. Buffett put Captain Tony’s on the international map when he recorded the song “Last Mango in Paris” in 1985.
Although Tarracino decided to sell Captain Tony’s Saloon in 1989, he continued to visit the bar on a regular basis until he died. He built up a fan following during his tenure as owner and he wanted to keep in touch with the people who helped his business flourish. Good times continue to happen at this historically amazing bar where people go to have the time of their lives. The luckiest of tourists may also get a close-up glimpse of one of their favorite celebrities at the same time and that is what makes Captain Tony’s Saloon one of the most interesting things to do in Key West.
