Sloppy Joe’s Key West: History, Events, and Visitor Guide

There is no more famous bar in America’s southernmost city, and maybe no more famous bar in Florida, than Sloppy Joe’s. You’ll see its name on more T-shirts than you can count, hear its bands spilling onto Duval at every hour, and watch a steady river of visitors pose under the green awning at the corner of Duval and Greene. It would be easy to write it off as a tourist trap—plenty of people do—but that misses the point. Sloppy Joe’s is a tourist trap the way the Eiffel Tower is a tourist trap: it became one by being genuinely, historically extraordinary first.

This is the full story—how a Prohibition-era speakeasy became a Hemingway landmark, the wild midnight move that relocated the whole bar in 1937, the truth about which building is the “real” one, and everything you need to actually enjoy a visit today. It’s the deep dive that pairs with our complete Duval Street bars guide.

Sloppy Joe’s at a Glance

You’ll find Sloppy Joe’s at 201 Duval Street, on the corner of Duval and Greene in the heart of Old Town. It’s open daily—roughly 9 a.m. to 4 a.m., a touch later in the morning on Sundays—with a full kitchen until late and live bands essentially all day and night. There’s no cover and no reservations; you walk in, find the music, and order a Sloppy Rita. It’s a working bar with a great kitchen and a famous name, not a museum, and that’s exactly how the regulars like it. (Hours and policies shift, so confirm current times before a special trip.)

The History: Born the Day Prohibition Ended

Sloppy Joe’s opened its doors on December 5, 1933, the day the Twenty-first Amendment repealed Prohibition. The timing was no accident. Its founder, Joe Russell—a Key West “Conch,” charter-boat captain, and former rumrunner—had been running liquor and operating speakeasies through the dry years. The moment it became legal to sell a drink openly, he did.

Russell’s first spot was a doorless dive he leased for three dollars a week at 428 Greene Street. He first called it the Blind Pig, then renamed it the Silver Slipper after adding a dance floor, before it settled into the name that stuck. For about three and a half years, this little Greene Street room was Sloppy Joe’s—and it’s where the bar’s most famous patron did his drinking.

The Hemingway Connection

Ernest Hemingway arrived in Key West in 1928 and quickly fell in with Joe Russell, who became his fishing companion for more than a decade—Russell piloted Hemingway’s boat on countless trips, including one legendary stretch of 54 marlin in 115 days. Their friendship was the real thing, not a marketing angle invented later.

The lore runs deep. Russell cashed a royalty check for Hemingway when a Front Street bank refused the rumpled, flip-flop-wearing writer. Hemingway nicknamed him “Josie Grunts” and immortalized him as Freddy, the bar-owning boat captain in To Have and Have Not (1937). Hemingway is said to have met his third wife, the journalist Martha Gellhorn, at the bar. And in a detail that says everything about how at home he felt there, Hemingway left a trove of his possessions—manuscripts, letters, even uncashed checks—in the bar’s back room, where they reportedly sat until his fourth wife, Mary, retrieved them in 1962, a year after his death. To trace the rest of his island footprint, our Hemingway House guide picks up the story at his Whitehead Street home.

Why Is It Called “Sloppy Joe’s”? The Havana Origin Story

The name didn’t start in Key West—it started in Havana. Hemingway suggested it, borrowing from a bar and fish market in Cuba run by a man named José García. The Havana spot’s floors were perpetually wet from the melting ice used to chill its seafood, and patrons teased the owner about running such a “sloppy” place. The nickname stuck, crossed the Florida Straits with Hemingway’s blessing, and gave Joe Russell’s bar its identity. The original Havana Sloppy Joe’s drew Hollywood royalty in its heyday, faded after the Cuban Revolution, and was eventually restored and reopened decades later—a nice piece of trivia to drop when someone assumes the name was born on Duval.

The Night Sloppy Joe’s Disappeared: The 1937 Move

This is the story locals love best. In 1937, Russell’s landlord raised the Greene Street rent from three dollars a week to four. Russell, never one to be pushed around, had quietly bought a building a block away—the former Victoria Restaurant at the corner of Duval and Greene—for $2,500.

On the night of May 5, 1937, with the lease expired and the landlord conveniently out of town, Russell and a “midnight mob” of patrons simply moved the entire bar. They carried everything—stools, tables, fixtures, the whole operation—down the street to 201 Duval, drinks reportedly still in hand, and the bar never actually closed. Hemingway, off in Spain at the time, supposedly heard the news and responded, “only in Key West.” The bar has been at the corner of Duval and Greene ever since, which is why its signs proudly read “Since 1937.”

Captain Tony’s vs. Sloppy Joe’s: Which Is the “Original”?

Here’s the confusion that trips up nearly every visitor, sorted out once and for all. The building at 428 Greene Street—where Sloppy Joe’s actually operated from 1933 to 1937, and where Hemingway did his real drinking—is today Captain Tony’s Saloon, renamed after Tony “Captain Tony” Tarracino bought it in 1968. The name and business “Sloppy Joe’s” moved one block to 201 Duval in 1937 and remains there.

So both claims are true, just to different parts of the story. If you want to stand in the room where Hemingway drank Sloppy Joe’s-era beers, go to Captain Tony’s. If you want the bar that has carried the Sloppy Joe’s name and spirit for the better part of a century, go to 201 Duval. Smart visitors do both—they’re a two-minute walk apart. And while we’re correcting myths: Sloppy Joe’s, for all its fame, is not the oldest bar in Key West. Captain Tony’s occupies the oldest bar building (dating to the 1850s), and the Green Parrot is often cited as Florida’s oldest continuously operating bar. Our Key West history guide untangles more of these threads.

Visiting Sloppy Joe’s Today: What to Expect

Walk in off Duval and the first thing that hits you is the volume—a band mid-set, a crowd two or three deep at the long bar, ceiling fans pushing the warm air around, and decades of Hemingway photos and memorabilia on the walls. It’s big, loud, and friendly, and the energy ramps up as the day goes on. Midday is family-friendly and easygoing; by night it’s a full-throttle party. The bar is open all ages until around 9:30 p.m., after which it’s 21 and over—bring ID if you’re arriving late. There’s even a set of live webcams on the bar’s website if you want to gauge the crowd before you walk over.

Live Music at Sloppy Joe’s

Music is the heartbeat of the place. Sloppy Joe’s books live bands daily, essentially continuously from late morning until the early hours, rotating through multiple acts on the main stage. You’ll hear everything from Buffett-style island rock to classic-rock covers and originals, and the bands know how to read a Duval crowd. It’s a cornerstone of the island’s scene—see our Key West live music guide for the full lineup of venues—but if you only catch one stage on Duval, this is the one that’s always going.

What to Eat and Drink

People forget Sloppy Joe’s has a genuinely good kitchen. The must-order is the Original Sloppy Joe Sandwich—seasoned ground beef with celery, onions, and peppers in a sweet tomato sauce, the dish that helped make the name famous. Beyond that, lean into the Keys and Cuban flavors: conch fritters with key lime mustard, smoked fish dip, a proper Cuban mix sandwich, and mahi tacos. Finish with key lime pie, naturally.

On the drinks side, the award-winning Sloppy Rita margarita is the signature, the frozen Rum Runner is pure Florida Keys, and the house-branded ales let you drink the logo as well as wear it. It’s bar food done well, not fine dining—if you’re after a white-tablecloth night, our Key West fine dining guide has you covered—but for a burger and a margarita with a live band, it delivers.

Hemingway Days & the “Papa” Look-Alike Contest

If you can time it, come in July for Hemingway Days, the island-wide celebration of its most famous resident. The centerpiece is the “Papa” Hemingway Look-Alike Contest, held at Sloppy Joe’s, where dozens of stout, white-bearded gentlemen in fishermen’s sweaters compete to channel the great man—a tradition the bar has hosted for more than four decades. The festival also features a mock “Running of the Bulls” outside the bar, a marlin tournament, and events at the Hemingway Home. Exact dates shift each year (it’s usually the third or fourth week of July), so check the festival calendar before booking. For the bigger picture of the island’s calendar, see our Key West events guide.

Sloppy Joe’s Merch: The Most Famous T-Shirt in Key West

The Sloppy Joe’s T-shirt is practically a Key West souvenir requirement—you’ll spot the logo in airports nationwide, worn by people remembering a good night on Duval. The bar runs a dedicated retail store just off Duval on Greene Street, plus an online shop, with the full range of tees, tanks, hats, and drinkware. Even if you skip everything else, grabbing a shirt at the source beats buying a knockoff three blocks away.

Ownership Through the Decades

Joe Russell ran the bar until his sudden death in 1941, while visiting Hemingway in Havana—a fittingly entwined end to their friendship. The bar passed through his family and later other hands, and since 1978 it has been owned by Sloppy Joe’s Enterprises, run by the families who bought it that year and have stewarded its growth into the global brand it is today. Along the way it earned a place on the National Register of Historic Places, formal recognition of what locals always knew: that this corner of Duval is a genuine piece of American cultural history, not just a good bar with a famous name.

Is Sloppy Joe’s Worth It?

Let me give you the honest answer, because plenty of travel snobs will tell you to skip it. Yes, it’s crowded. Yes, it’s touristy. Yes, you’ll pay Duval prices and the merch is everywhere. And yes, it’s still absolutely worth going. There’s something genuinely moving about standing in a bar that opened the night Prohibition ended, hearing live music in the same spot where the name became famous, and feeling the weight of nearly a century of stories. Go in with the right expectations—it’s a lively, historic party bar, not a quiet shrine—and you’ll have a great time. The trick, as with most of Key West, is to visit on your own terms: earlier in the day, with cash for the band, and a willingness to let the place be exactly what it is.

Tips for Visiting

A few things I’d tell a friend: go midday or mid-afternoon if you want to actually hear the band and find a seat—the crowds thicken fast after dark. Check the bar’s webcams to time your arrival. Bring a little cash for tipping the bands and bartenders. If you’re doing the full Duval crawl, make Sloppy Joe’s an early-evening stop rather than a 1 a.m. one, when it’s wall-to-wall. And do walk the block to Captain Tony’s—standing in the original 1930s room is the part of the story most visitors never realize they missed.

Frequently Asked Questions

Why is it called Sloppy Joe’s?

Hemingway suggested the name, borrowing it from a Havana bar run by José García whose floors were always wet—”sloppy”—from the melting ice used to chill seafood. The nickname crossed from Cuba to Key West with Hemingway’s blessing.

Did Hemingway actually drink at Sloppy Joe’s?

Yes. He was a regular in the 1930s and a close friend and fishing companion of owner Joe Russell, who became the model for Freddy in To Have and Have Not. In Hemingway’s era the bar was at 428 Greene Street (now Captain Tony’s) until 1937, then at 201 Duval.

Is Captain Tony’s the original Sloppy Joe’s?

The building at 428 Greene Street—now Captain Tony’s Saloon—was the original 1933–1937 location of Sloppy Joe’s. The name and business moved to 201 Duval in 1937, where it remains. Both are tied to the story, just in different ways.

When did Sloppy Joe’s open?

December 5, 1933—the day Prohibition was repealed. Founder Joe Russell, a former rumrunner, opened the moment selling liquor became legal again.

Why did Sloppy Joe’s move?

In 1937 the landlord raised the rent by a dollar a week. Russell had bought a building a block away, and one night while the landlord was traveling, he and his patrons carried the entire bar to 201 Duval—drinks reportedly still in hand.

Is Sloppy Joe’s the oldest bar in Key West?

No. It’s historic (1933) but not the oldest. Captain Tony’s occupies the oldest bar building, from the 1850s, and the Green Parrot is often called Florida’s oldest continuously operating bar.

What is the famous sandwich at Sloppy Joe’s?

The Original Sloppy Joe Sandwich: seasoned ground beef with celery, onions, and peppers in a sweet tomato sauce. It’s the dish that helped make the bar’s name famous.

When is the Hemingway Look-Alike Contest?

Each July, during Hemingway Days, held at Sloppy Joe’s Bar. Exact dates shift yearly—usually the third or fourth week of July—so check the current festival calendar before planning around it.

Final Thoughts

Sloppy Joe’s earns its fame. Strip away the T-shirts and the cruise-ship crowds and you’re left with a bar that opened the day Prohibition died, kept Hemingway’s company through his Key West decade, and once got up and walked itself down the street rather than pay an extra dollar in rent. Order the sandwich, tip the band, and take the two-minute detour to Captain Tony’s to see where it all started. Then keep the night going with our Key West nightlife guide—Duval is just getting warmed up.