Qualla: Captain Tony's Saloon: The Bar Hemingway Left Behind

Captain Tony's Saloon: The Bar Hemingway Left Behind: Introduction

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Bubba73, CC BY-SA 3.0. When the landlord at 428 Greene Street raised the rent by one dollar a week in 1938, Josie Russell did not negotiate. He and his customers picked up the entire bar -- stools, bottles, everything -- and moved it down the block to 201 Duval Street, where it became the Sloppy Joe's that tourists line up for today. The original building sat empty. Nobody realized they had left behind the most storied address in Key West. The place where Hemingway actually drank, where the news of the USS Maine's destruction was telegraphed to the world, where bootleggers poured rum during Prohibition -- that building is Captain Tony's Saloon, and it has been accumulating history like barnacles on a hull since 1851.

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Image: Bubba73 | CC BY-SA 3.0

Captain Tony's Saloon: The Bar Hemingway Left Behind: Ice, Death, and Morse Code

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Abraham Ortelius, Public domain. The building at 428 Greene Street started life in 1851 as an icehouse that doubled as Key West's city morgue -- a practical combination in a tropical port town where ice was precious and bodies needed keeping cool. By the 1890s, the building housed a wireless telegraph station, a...

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Image: Abraham Ortelius | Public domain

Captain Tony's Saloon: The Bar Hemingway Left Behind: Hemingway's Real Bar

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Bubba73, CC BY-SA 3.0. In the early 1930s, a local named Josie Russell bought the business at 428 Greene and created Sloppy Joe's Bar. Ernest Hemingway, who lived in Key West from 1931 to 1939, became a regular. Between 1933 and 1937, Hemingway spent most of his evenings here, drinking with Russell and...

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Image: Bubba73 | CC BY-SA 3.0

Captain Tony's Saloon: The Bar Hemingway Left Behind: The Captain Takes the Helm

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Bubba73, CC BY-SA 3.0. In 1968, Tony Tarracino -- a charter boat captain with a gift for storytelling and an outsized personality -- purchased the bar from Wolkowsky and renamed it Captain Tony's Saloon. Tarracino was a local legend: a New Jersey transplant who had come to Key West on a shrimp boat and...

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Image: Bubba73 | CC BY-SA 3.0

Captain Tony's Saloon: The Bar Hemingway Left Behind: Where Margaritaville Began

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Bubba73, CC BY-SA 3.0. In the early 1970s, a young singer-songwriter named Jimmy Buffett drifted into Key West and started playing at Captain Tony's. He was often paid in tequila. The bar became his launchpad -- the place where Buffett developed the Caribbean-tinged, laid-back persona that would make h...

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Image: Bubba73 | CC BY-SA 3.0

Captain Tony's Saloon: The Bar Hemingway Left Behind: Still Standing at 428 Greene

Mon, 23 Feb 2026 00:00:00 GMT

Photo credit Bubba73, CC BY-SA 3.0. Captain Tony's Saloon is not polished. The ceiling is hung with bras and business cards. The walls are covered with license plates, photographs, and decades of accumulated ephemera. A tree grows through the roof. It looks nothing like the sanitized Hemingway experience available ...

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Image: Bubba73 | CC BY-SA 3.0