June 6, 2026 - South Florida and Bahamas Cruise
Shark Valley, Florida Keys, Key West
ZZZ
It connects Knight's Key (part of the city of Marathon) in the Middle Keys to Little Duck Key in the Lower Keys. Among the longest bridges in existence when it was built, it is part of the Overseas Highway in the Keys, which is part of the 2,369-mile U.S. Route 1.
When I'm in Key West, it is mandatory that I go to Sloppy Joe's. We are here! My Papa Doble is on order.
Here's how to make a Papa Doble (Hemingway's special Daiquiri):
Serve in a Martini (large 10oz) glass
Ingredients:
3 1⁄2 fl oz Light gold rum (1-3 year old molasses column)
1 fl oz Pink grapefruit juice (freshly squeezed)
3⁄4 fl oz Luxardo Maraschino liqueur
1 fl oz Lime juice (freshly squeezed)
1⁄2 fl oz Sugar syrup 'rich' (2 sugar to 1 water, 65.0°Brix)
Prepare:
Select and pre-chill a MARTINI (LARGE 10OZ) GLASS.
Prepare garnish of Luxardo Maraschino Cherry &/or lime wedge/wheel.
How to make:
SHAKE all ingredients with ice.
FINE STRAIN into chilled glass.
Garnish:
Garnish with mraschino cherry &/or lime wedge/wheel.
Capt. Tony's Saloon is one of the most historic—and legendary—bars in Key West. Its story spans more than 170 years and reflects much of the island's colorful past.
The building at 428 Greene Street was constructed in 1851 as an ice house, at a time before mechanical refrigeration. Because it was one of the coolest buildings in town, it also served as the city morgue. Over the next several decades, it had a remarkable series of uses: wireless telegraph station, cigar factory, bordello, speakeasy, the original Sloppy Joe's, and finally Captain Tony's Saloon.
In 1933, local bar owner Joe "Josie" Russell purchased the building and opened Sloppy Joe's Bar. The name was suggested by his friend Ernest Hemingway, who borrowed it from a favorite Havana establishment they both visited. Between 1933 and 1937, Hemingway spent many evenings here. The bar featured gambling, live rumba music, dancing, and a lively clientele typical of pre-war Key West. It was a rough-and-tumble fishermen's bar with sawdust on the floor, gambling, cheap beer, and ten-cent shots of gin.
In 1938 when the landlord raised the rent by $1 per week, Russell and his customers reportedly dismantled the bar overnight and physically moved it several blocks to 201 Duval Street, where Sloppy Joe's Bar remains today. The bar never actually closed during the move. Customers simply carried their drinks with them to the new location, where the party continued until morning.
After changing hands several times, the building was acquired by Tony Tarracino, a charter fishing captain, former rum-runner, gambler, and later mayor of Key West. He renamed it Captain Tony's Saloon in the late 1950s/1960s.
The saloon became closely associated with Jimmy Buffett, who played there in the early 1970s while establishing himself in Key West.
Regular patrons who became famous have their names painted on individual stools, including Hemingway, Harry S. Truman, John F. Kennedy, Truman Capote, John Prine, and Jimmy Buffett.
Above the entrance hangs a preserved Atlantic goliath grouper caught by Captain Tony. Visitors traditionally toss quarters into its open mouth for good luck.
Despite Key West's transformation into a major tourist destination, Captain Tony's has deliberately retained the atmosphere of an old island dive bar. Live music continues daily, and its walls are packed with decades of memorabilia, making it one of the most visited historic watering holes in the Florida Keys.
Sloppy Joe's Bar is the same business as Captain Tony's Saloon, but it has operated from 201 Duval Street since its famous overnight move in 1937.
Hemingway and Joe Russell frequently visited Sloppy Joe's Bar in Havana, Cuba, owned by José García. Because the floor there was perpetually wet from melting ice used to chill seafood and drinks, patrons jokingly called it "Sloppy Joe's." Hemingway suggested Russell adopt the same name for his Key West establishment, and it stuck.
