A big claim to fame of Sloppy Joe’s bar in Key West was that it was a favorite haunt of legendary author Ernest Hemingway, who lived on Key West for most of the 1930s.
Until my visit to Key West in January 2017, I had no idea that the current Sloppy Joe’s property (shown in the lead-off photo), which fronts Duval Street at the intersection of Greene Street, was not the same place Hemingway visited.
From the time the bar opened in 1933 until 1937, Sloppy Joe’s was a half-block west on Greene (see first photo below), a place that now operates as Capt. Tony’s Saloon. Hemingway owned his home in Key West from 1931-39, so most of the time he dropped into Sloppy Joe’s was when it was at the original site.
The Wikipedia entry for Sloppy Joe’s Bar indicates that there is no evidence Hemingway stopped into the bar after it moved, so I feel a bit cheated thinking, since my first visit last year, that I had been in the same place where Hemingway tipped his elbow. I didn’t stick my head inside the door of Capt. Tony’s to check it out, but it did not appear to be a very spacious place. Not even close to the room in the current Sloppy Joe’s.
Today’s Sloppy Joe’s has live entertainers throughout the day. The performer shown in the photo above and next two below started his set about 10 minutes after our arrival during the 2018 visit to the Keys. A couple from Put-In-Bay Island, Ohio, who sat at our table with us, said they were acquainted with the performer, who they said managed to get a gig in Key West at the same time the group from Put-In-Bay made its annual trek to the Keys. The guy in the third photo below was near the end of his gig when we arrived.
In the January 2017 visit, this solo artist was performing on stage when we stopped at the bar. He paused for a nice close shot (first photo below). Then during a break, he sat at a side bar with his little four-legged companion, who happened to peak out at us at our table (second photo below).
Above and below: A look at some of the decor in Sloppy Joe’s. A ceiling sign (above) promoting the bar’s carry-out frozen coolies. Although open containers of alcohol in public are illegal in Key West, there has been a long-standing policy for police to not bother people with alcoholic beverages on the core downtown streets, especially if you use a plastic cup and behave responsibly. The bartenders told us that police also recognize these frozen coolie containers and will allow the use of alcoholic drinks in them on the streets. This sign was within close eyeshot of our table, so I studied the options several times over and decided to get either the rum runner or the pain in the ass. I think it was the latter. Whichever, it was very good (photo below), and I sipped from it when we resumed our stroll along Duval Street afterward.
The entrance and checkout area of the bar (above), with a closeup of the Life magazine cover photo of Hemingway below.
Coming up next: Margaritaville, Key West
Previously in FLORIDA:
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