corner, the actual drinking hole of Hemingway. In 1938, the owner of Sloppy Joe’s saw the rent of the building that housed his bar raise considerably. As the tale goes, the landlord seemed to think that because the bar was so popular the owners would have no problems paying the increased rent. The landlord was correct in just half that statement – it was no problem – for the whole bar to shut down and move around the corner onto Duval Street where they received lower rent, and continued as if nothing happened. Thing is, Hemingway was already out of town by the time Sloppy Joe’s took up its new residence, having left town just a couple of years prior.
“In other words, if you want to really drink where Hemingway drank you’ll have to move your solo party around the corner to Captain Tony’s,” said my own personal professor.
While the daiquiris were good, and my bar stool had seemed to rise by three feet, I bid the man adieu and headed around the corner.
Being that Key West is known for Duval Street, and not Greene Street, this road, and this establishment, were far less crowded than the one I had just come from. Now, this is how I pictured Hemingway’s Key West. In a place like the current Sloppy Joe’s, especially if it were modern day, Hemingway would have been pestered by autograph and picture seekers between every drink of his daiquiri. It’s hard to imagine that he wouldn’t have said, “The hell with this,” and moved his drinking to his own sizable house – or at a place like Captain Tony’s.
Despite seeming like less of a tourist trap than Joe’s, Tony’s still had a reminder here and there that Hemingway once walked those floors. The biggest reminder of that was a bar stool – THE barstool – that Hemingway sat on when he drank here. In addition to a bar stool with his name on it, there were ones with the names of Truman Capote, Shel Silverstein, John F. Kennedy, and Jimmy Buffett, among others. I chose the Walter Cronkite stool, as the Hemingway stool was taken just before I could scoop it up.
Here I ordered another daiquiri or three, and walked around. Despite losing the name “Sloppy Joe’s” and most of Hemingway’s tourist traffic to the establishment on Duval Street, this place holds tons more charm. I’ll go out on a limb, perhaps the limb of the tree that sits right in the middle of Captain Tony’s, that if Hemingway came back today and had to choose between the two bars he’d most likely be sitting right next to me on his stool.
I learned from the bartender here, an older man named Hess, that the barstool with Buffett’s name on it is usually warm, because whenever he is in Key West – his permanent residence – he does most of his drinking at Tony’s. In fact, legend has it, he even wrote a song about this bar and its longtime owner, the captain himself, Tony Tarracino. Buffet will always be grateful to Tarracino because Buffet got his start there. The rumor is Tarracino usually paid him in tequila instead of cash. If you’ve heard just a few Buffet songs you get the impression that this arrangement was just fine with him.
Hess told me that Tarracino sold the bar in 1989, but still showed up once a week until his death in 2008 just to greet new customers and shoot the breeze with the long-standing ones. The new owner, of course, didn’t mind Tarracino’s presence because it brought in quite a revenue stream.
In addition to having a tree centered right in the middle of the bar, there are also thousands of business cards lining the walls, some of them 30 and 40 years old. It was almost enough for me to wish I had a business card of my own to post on the wall just to join the others.