Key West, Florida

End of the Line

December 2021

Article and photos by Jimmy Jacobs.

Capt. Tony’s Saloon in Key West is one of Florida’s quintessential watering holes. Besides having a bar that is a good place to end a day of fishing over a cold beverage, it is steeped in history.

While tourists pile into Sloppy Joe’s, just down the street at the corner of Duval and Greene streets for their dose of Hemingway’s Key West, few realize that from 1933 to 1937 the Sloppy Joe’s that the writer frequented was in the building now housing Capt. Tony’s. Indeed, if you visit the Hemingway House, you’ll see the porcelain watering trough in the yard for Ernest’s famed six-toed cats. That fixture started life as a urinal at what is now Capt. Tony’s, but when the establishment moved down the street, the urinal instead was taked to its present location.

The establishment’s history goes even farther back in Key West’s past too. Built in 1851, it started life as an ice house that doubled as the Key West mortuary. It provided a quite convenient site for that latter business, since the tree that still protrudes through the roof of the bar was the city’s “hanging”tree, where executions took place!

Fast forward to the year 1958, when Capt. Tony Tarracino purchased the business and renamed it. Capt. Tony was a charter boat captain, but in earlier years listed occupations of boot-legger, professional gambler, gun runner and casino owner. Also, on his fourth try, he was elected mayor of Key West and among those campaigning for him was Jimmy Buffet. Buffet performed at Capt. Tony’s Saloon in the early 1970s, as he was getting started in the music business. Supposedly, he often was paid for his work with tequilla. The singer immortalized both the bar and Capt. Tony in his song “Last Mango in Paris.”

Even after Capt. Tony sold the bar in 1989, he continued to show up  weekly until his death in 2008. While visiting the saloon during Fantasy Fest in the late 1990s , I recognized Capt. Tony standing near the gift shop counter. He was flanked by young ladies dressed in body paint – one painted as a tiger and the other as a lion.

Today Capt. Tony’s remains a must see in the city that has been called the End of the Line.