Captain Tony's Saloon stands at 428 Greene Street in a building constructed in 1851 that has housed a morgue, ice warehouse, telegram station, cigar factory, bordello, speakeasy, and casino before becoming a bar. The space is most famously remembered as the original Sloppy Joe's Bar, where Ernest Hemingway spent his evenings from 1933 to 1937. Josie Russell, a fishing friend of Hemingway, opened Sloppy Joe's on December 5, 1933—the day Prohibition was repealed in the United States. The bar's name honored a Havana establishment where Hemingway and Russell had been patrons. In 1938, when the building's landlord raised rent by one dollar per week, Russell relocated the bar and its customers to a new location at Duval Street, where Sloppy Joe's continues to operate today.
In 1958, charter boat captain Tony Tarracino purchased the Greene Street location and renamed it Captain Tony's Saloon. Tarracino became a Key West fixture—a gunrunner, casino operator, and mayor—whose larger-than-life personality shaped the bar's identity. The space retains a historic live oak tree growing through the structure and carries local tradition that the tree was once used for executions. The bar preserves its literary legacy: stools are painted with the names of Ernest Hemingway, Truman Capote, Jimmy Buffett, Tennessee Williams, and Shel Silverstein—the constellation of artists who drank and worked in Key West across decades. The combination of documented Hemingway connection, architectural history, and cultural significance makes Captain Tony's a primary historical venue in Old Town.
Common Questions
What is the connection between Captain Tony's and Ernest Hemingway?
Captain Tony's occupies the building that housed the original Sloppy Joe's Bar, where Hemingway was a regular patron from 1933 to 1937 during his most productive years as a writer in Key West. The bar was owned and operated by Hemingway's fishing friend, Josie Russell.
What historical events took place at this location before it became a bar?
The building at 428 Greene Street, constructed in 1851, served variously as an ice warehouse, city morgue, wireless telegraph station (during the Spanish-American War), cigar factory, bordello, and speakeasy with gambling operations before becoming Sloppy Joe's Bar in 1933.
Why did Sloppy Joe's move locations in 1938?
The bar relocated because the building's landlord raised the rent by one dollar per week. Josie Russell and the bar's customers moved to a new location at 201 Duval Street, where Sloppy Joe's continues to operate today.