December 1, 2016

Sloppy Joe's Bar in Key West, Florida

Sloppy Joe's Key West Florida Exterior from Duval

photo by: Sam Howzit/Flickr/CC BY 2.0

The circa 1917 brick-and-stucco building sits on Duval Street, Key West's main throroughfare.

On the day Prohibition was repealed, the liquor lovers of Key West, Florida, rejoiced by opening Sloppy Joe’s Bar. Four years later, in 1937, the watering hole moved into a vacated Cuban restaurant on the corner of Duval and Green streets. It’s been there ever since.

The story goes that the move was less of an official endeavor, and more of a slight interruption in the bar’s daily activity. Patrons simply got up from their stools, walked across the street to the establishment's present-day location, sat down, and resumed their drinking and conversation. That’s the kind of easy-going attitude you’ll find in Key West, and certainly inside Sloppy Joe’s.

The bar has been associated with Ernest Hemingway, who, drawn to the laid-back lifestyle of the area, purchased a nearby Spanish-style villa and set up shop in Key West in the 1930s. Then owner, Joe Russell, a proprietor of illegal speakeasies and a personal friend of Hemingway's, agreed to name the institution after the writer's favorite drinkery in Havana, Cuba.

Sloppy Joe's Key West Florida Historic 1950s Photo of Patrons

photo by: Monroe Country Library Collection

Sloppy Joe's has never flagged in popularity, as this photograph taken in the 1950s shows.

Hemingway wasn’t the only person from the early 20th century literary and artist scene to patronize the iconic establishment. His cohorts, including Waldo Pierce, Captain Eddie Saunders, and John Dos Passos could often be seen spread out comfortably at the bar, drinking tequila, and enjoying the ocean breezes filtering through the structure’s jalousie doors.

Today, the bar is an amalgamation of 1930s glory days memorabilia and trinkets that unassumingly remind patrons that Sloppy Joe’s isn’t a tourist trap, but a cultural experience you won’t find elsewhere. A 119-pound sailfish, proudly caught by Hemingway, shares space on the wall with a bat used to inspire fear in otherwise rowdy patrons. The long wooden bar, once the longest in town, has well-worn patches and dings in it that celebrate the beloved establishment’s hallowed past.

The motley history of Sloppy Joe’s encourages thousands of tourists and literary lovers to take a seat under the creaky fans, hoping for a little inspiration and good karma from the historic notables who came before them.

Sloppy Joe's Key West Florida Ernest Hemingway Memorabilia

photo by: Ian/Flickr/CC BY NC 2.0

Sloppy Joe's proudly displays its connection with one of America's greatest writers on its wood-paneled walls.

Location: 201 Duval St., Key West, FL 33040

Hours: Open 365 days a year. Monday-Saturday, 9 a.m.-4 a.m.; Sunday, noon-4 a.m.

You’re having: A ropa-vieja-style ground beef sandwich, known colloquially as the “Sloppy Joe,” and the Sloppy Rita, a tangy tequila-based drink with orange juice.

Best Yelp Review: “Atmosphere was wonderful, with live music smiling, laughing, joking servers and bartenders and busboys.” –Kristie D.

Meghan White is a historic preservationist and a former assistant editor for Preservation magazine. She has a penchant for historic stables, absorbing stories of the past, and one day rehabilitating a Charleston single house.

Share your stories from Route 66! Whether a quirky roadside attraction, a treasured business, or a piece of family history, we are looking for your stories from this iconic highway.

Share Your Story