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Sloppy Joe’s Orlando

Written By Scott Joseph On June 2, 2022

Sloppy sign

I wonder what Papa would make of it all.

As legend has it, Ernest Hemingway was a regular of a Key West bar that would eventually become known as Sloppy Joe’s. According to the website of the newest Sloppy Joe’s, at Orlando’s Icon Park on International Drive, it was actually Hemingway who suggested the name. And today he is very much a part of the brand image, with his likeness on cocktail glasses, annual look-alike contests and, here, his quote above the bar (which has a large mirror with “Papa’s Pilar Rum” on it) that reads, “I drink to make other people more interesting.” (The quote has his signature but I don’t think he really signed it.)

Southeast Black November

Sloppy screens

Sloppy bar

The Key West bar long ago became more of a tourist destination than a locals’ hangout. So it’s fitting that Orlando’s is located in Tourist World. But that said, the Orlando Sloppy Joe’s is a pleasant, if a bit contrived, bar and restaurant, and it actually serves some good food.

There is, of course, a sloppy joe sandwich even though few people think that it originated in Key West. (Most believe it was first concocted at a restaurant in Sioux City, Iowa; others think it may be a sandwich version of Cuba’s ropa vieja.) But I’ve always had a policy that if a dish bears the restaurant’s name, it’s probably something worth ordering.

Sloppy joe

And it was. And to be technical, the menu lists it as “the big sloppy with cheese,” which is what it was. The tomato-sauced ground beef was served on a sesame bun with a load of melted cheeses (Colby and jack) on top. More gloppy than sloppy. I had it with fries, which were also pretty good, with a crispy outside and moist potato meat inside.

Sloppy cuban

The menu’s Cuban sandwich is also not called a Cuban sandwich, instead it’s a Havana. Also a good sandwich, it had loads of sliced roast pork, ham and salami with cheese, the requisite pickle slices and yellow mustard pressed in Cuban bread. I might go so far as to say it’s one of the better Cuban sandwiches I’ve had in town. I know it’s the best Havana sandwich. This one came with black beans and rice, which needed a bit of seasoning.

Sloppy buoy

Sloppy ronnie

The decor is a bit too pristine to be authentic Key West but it does feature large screens with live shots of Mallory Square and a countdown clock to sunset, so even that bit of tourist trapism can be experienced. There is also a replica of the iconic buoy that marks the Southernmost Point in the U.S. outside. And a wall inside has photos of Key West and, for some reason, the old Ronnie’s restaurant on Colonial Drive.

Our server was very good and personable, though I don’t think it’s necessary for servers to hand out business cards to customers.

I’m guessing they don’t do that at the original restaurant, but I’ll admit it’s been a long time since I visited that one. There’s no reason to now.

Sloppy Joe’s is at 8371 International Drive, Orlando (map). It is open for lunch and dinner daily. The phone number is 407-698-5485.

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