You've probably seen the shirts. Maybe you even own one—that classic, slightly weathered logo of a bearded man that screams "I went to the Florida Keys and survived Duval Street." But honestly, most people who walk through the jalousie doors of Sloppy Joe's Key West have no idea they are standing in the middle of a decades-long geographical feud.
It’s the kind of place where the history is as thick as the humidity.
If you're planning a trip to the Southernmost City, you basically have to stop here. It’s a rule. But before you order your first Papa Dobles, you should know that the building you’re standing in wasn't actually the original spot where Ernest Hemingway did his heaviest drinking.
That’s the first thing people get wrong.
The Midnight Move and a Stolen Urinal
The story of how Sloppy Joe's Key West ended up at the corner of Duval and Greene is peak Key West. Back in 1933, on the literal day Prohibition was repealed, Joe Russell opened his bar. At first, it was a gritty little hole-in-the-wall called the Blind Pig, then the Silver Slipper.
It was located just around the corner at 428 Greene Street. Today, that spot is Captain Tony’s Saloon.
So, why did they move? Money. It’s always money. In 1937, the landlord decided to hike the rent from $3 a week to $4. Joe Russell, being a man of principle (and presumably a bit of a cheapskate), refused to pay the extra buck.
Instead of negotiating, Joe and his regulars—including Hemingway—decided to move the entire bar. In the middle of the night.
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They didn't even close. Patrons simply picked up their drinks, grabbed their favorite barstools, and carried the furniture down the street to the new location at 201 Duval Street. Hemingway himself allegedly walked out with the urinal from the men's room, claiming he had "pissed enough of his money away into it" to own it. That urinal still exists today, but you won't find it at the bar; it’s currently a water fountain for cats at the Hemingway Home and Museum.
Why Hemingway Actually Liked This Place
Hemingway wasn't just a celebrity endorsement. He and Joe Russell were genuine friends. Russell was a pilot and a boat captain who helped Hemingway with his fishing exploits and, during the "dry" years, probably helped him with a bit of rum-running too.
In fact, if you read To Have and Have Not, the character of Freddy is based directly on Joe Russell.
When you walk into Sloppy Joe's Key West today, look up. You’ll see a 119-pound sailfish mounted on the wall. Hemingway caught that. You'll also see "Big" Skinner's bat. Skinner was the legendary 300-pound bartender who kept the peace during the bar’s rowdiest years. If things got too sideways, that bat came out.
It’s a different vibe now, obviously. More tourists, fewer fistfights. But the bones of that "Conch" atmosphere are still there if you look past the neon signs.
What to Eat (and Drink) Without Looking Like a Total Rookie
Most people come for the name and stay for the live music, which starts at noon and doesn't stop until 4:00 AM. But the menu is actually surprisingly decent for a place that pumps out that much volume.
The signature dish is, predictably, the Sloppy Joe sandwich. It's the classic ground beef, onions, peppers, and secret spices. It’s messy. It’s exactly what you want after three rums.
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Pro Tip: If you want to drink like "Papa," don't just order a generic mojito. Ask for the Papa Dobles.
The Hemingway Daiquiri (Papa Dobles)
Hemingway was a diabetic, so he didn't like sugar in his drinks. He liked them strong and tart. The traditional recipe used at the bar includes:
- White Rum (lots of it)
- Fresh Grapefruit Juice
- Maraschino Liqueur
- Fresh Lime Juice
It’s shaken until it’s ice cold and served without sugar. It’ll wake you up. Or knock you down. Depends on the day.
If you aren't feeling the beef, the Conch Fritters are a staple here. They serve them with a key lime mustard that’s actually pretty sharp. Also, look for the Royal Red Shrimp if they have them—they’re deep-water shrimp that taste almost like lobster.
The Papa Look-Alike Contest: Peak Key West Weirdness
If you happen to be in town in late July, specifically around Hemingway’s birthday (July 21st), prepare for the sea of white beards.
The Sloppy Joe's Hemingway® Look-Alike Contest is a massive deal. We’re talking 150+ men from all over the world who spend all year grooming their facial hair and perfecting their "stoic writer" gaze. It’s held on the main stage at Sloppy Joe's Key West and it is intense.
It’s not just about the beard. There’s a "Running of the Bulls" (where the "bulls" are fake and the men are mostly middle-aged), a fishing tournament, and a lot of storytelling. 2026 marks the 45th year of this madness, and it’s scheduled for July 22-26. If you want a seat during the finals on Saturday night, you basically have to get there at breakfast and never leave.
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The Reality of Visiting in 2026
Let’s be real for a second. Sloppy Joe's Key West is a tourist trap.
There. I said it.
It’s loud. It’s crowded. The gift shop is massive. But it’s one of those rare places that manages to be a tourist trap while still being authentic. The locals still drink there (usually earlier in the day at Joe’s Taproom next door). The musicians are some of the best on the island. And the history isn't manufactured; it's literally built into the walls.
Quick Logistics
- Hours: 9:00 AM to 4:00 AM (Mon-Sat), Noon to 4:00 AM (Sun).
- Crowds: Peak time is 9:00 PM to midnight. If you want to actually see the memorabilia, go for lunch.
- Live Cams: They have four live cams on their website. If you’re bored at work, you can watch the Duval Street crowds or the stage. It’s strangely addictive.
- Location: 201 Duval St, Key West, FL 33040.
Actionable Insights for Your Visit
Don't just walk in, take a selfie, and leave. To actually experience Sloppy Joe's Key West, do this:
- Go early for the history. Visit around 11:00 AM. The light is better for seeing the old photos, the sailfish, and the murals by Erik Smith.
- Check the Taproom. If the main room is too loud, Joe’s Taproom (connected to the main bar) has a massive selection of craft beers, including their own Sloppy Hoppy IPA, and a slightly more "local" vibe.
- Find the "Silver Slipper" mural. Look for the artwork depicting Joe Russell, Hemingway, and Skinner. It captures the 1930s era perfectly.
- Buy the shirt elsewhere (maybe). The gift shop is great, but there are tons of vintage-style Sloppy Joe's designs in the smaller boutiques off Duval that look a little less "I just stepped off a cruise ship."
- Visit Captain Tony's too. To get the full story, walk half a block to 428 Greene St. See the "Hanging Tree" that grows right through the roof of the bar. That’s where the original bar was. Drinking at both is the only way to settle the historical score.
Key West changes constantly, but Sloppy's feels like it’s anchored to the coral rock. Whether you're there for the history or just a very cold beer, it’s the heartbeat of Duval Street.
Next Steps:
Check the live music schedule on the official Sloppy Joe's website before you head out, as they often host surprise sets from well-known Florida musicians. If you're visiting during July, make sure to register for the Hemingway Look-Alike events months in advance, as hotels in the Old Town area sell out nearly a year ahead of the festival.