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Sloppy Joe's

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In 1933, a gallon of gas cost 10 cents-a loaf of bread? Only 7 cents. The movie King Kong had just premiered and the New York Giants at the Polo Grounds in Manhattan had won the World Series in 5 games.

Most importantly, though, on December 5th, after thirteen long and thirsty years - the 21st Amendment passed: finally repealing Prohibition.

On the very same day, Sloppy Joe’s officially opened its doors.

Or so the story goes, because most locals know that the famous rumrunner Habana Joe had already been using the spot as a bit of a base station and that the original bar had served drinks regardless of current legislation.

A few things have changed down in Key West since then, the rum’s still just as easy to find, gas is definitely a bit more expensive but Sloppy Joe’s is still standing just a few blocks down from where it all began.

And folks keep flocking there, I know I’ve made the pilgrimage several times myself - because in a lot of ways that’s what it is. You could call this “frozen drink oasis” one of America’s earliest sports bars - an institution that should be on any serious day-drinker or mojito lover’s bucket list.


When you walk into Sloppy Joe’s, regardless of the time of day or the day of the week, you can pretty much be guaranteed a good crowd. While a solid reputation for some of the best bar food on Duval Street (I’m looking at you Sloppy Joe fries!) and talented bartenders willing to chew the fat with just about anyone sure help keep the reputation going - 83 years of good-time-having momentum sure doesn’t hurt either.

Most nights the place is hopping with sunburnt tourists, salt stained sea captains, a good mix of locals and of course a laundry list of regulars chomping at the bit to regale you with one of their favorite Sloppy Joe glory stories.

Still on the fence about stopping by? Check out the live webcam to see the crowd beforehand - there’s a good chance your buddies are already bellied up to the bar.

A band tends to take the stage when the sun goes down to really get the party started while the blenders continue to spin. The ambiance is unmatched, with walls that are speckled with everything from postcards, marlins, and memorabilia, to full portraits of Sloppy Joe’s patron saint.

Papa himself - Ernest Hemingway.

Oh? You didn’t think I’d leave out the literary legend that had a bad habit of closing the place down, did you? Of course not, Hemmingway’s legacy is alive and well at Sloppy Joe’s with plenty of reminders scattered in and around the bar. Not to mention the look-alike contest hosted every mid-July (They’ve been running it since 1981.)

From frozen drinks that quench even the mightiest thirst and an attitude of “keep the good times rolling,” it’s no wonder that Sloppy Joe’s isn’t just a bar for most folks - it’s an institution.

When you lean against the well worn bar top and take that first ice-cold sip of your favorite libation - you're not just part of the party, you’re part of history!

If you want to check out the action, just click here: Sloppy Joes.


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