Hemingway Bars for the Best of Key West

hemingway bars, sloppy joe's
Sloppy Joes has plenty of Hemingway cultural notes, making it a great one of Hemingway bars

If you are planning to visit Hemingway bars where he drank when he lived on Key West, Florida, you have two stops to make. 

First To Captain Tony’s

Captain Tony’s Saloon in Key West is a dark hole with tables, a guitarist, a bar tender and a gnarled tree pushing up through the ceiling like the one that made a leg for Odysseus’ bed.  Really, it seemed to me to be the quintessential of Hemingway bars, a place that seems not to have changed much. On the walls, sticky tags from drink bottles and surf wear companies, hundreds of dollar bills and the odd business card are stapled to dark, dark wood.  A decent guitarist quietly plays Bob Dylan in front by the door.  It’s a dark hold of a place which, before it became Hemingway’s haunt in 1933, was reportedly the city morgue.

Of course we stopped there.  We took pictures.  And I tried to see if there was any part, besides the tree, that reminded me of Papa Hemingway, besides the picture of him fishing with the original bar owner, Captain Tony.

There might be something.  A whisper of age, of history.  The faintest odor of the sea which seeped into the boards over a hundred years.  The bricks on the floor to the right side of the bar, which might be where the ice was said to melt in a slurry that gave the place its name, “Sloppy Joe’s.” There was also this: the space resembles a ramshackle harbor bar of the type that they say Papa liked to go to, every day, after he finished his 500 written words.  He would come to drink and swap stories, stories that might eventually make it to, say, everyone who could read English.

It’s not surprising that it’s bare, since they say that when Captain Tony moved the bar down the street, he took out everything in it, including all the plumbing fixtures.  Including a urinal that later turned up at the Hemingway house, where it became a fountain and waterer for cats. This is the kind of story you find when you start sluffing around Hemingway bars.

As for me, the idea that Hem wrote 500 words a day is instructive. That would be … about a blog post every three days. What speed. One can only feel envious, writer to writer, of such stable production. 

Of course, what he was writing at this time, was Death in the Afternoon, his discussion of the Spanish tradition of bullfighting, which he believed was going to make his literary reputation, and which, as it turns out, was 1000 pages of stuff most people were not willing to read. He was angry, and then he wrote To Have and Have Not, which is a decent novel despite some lapses into non-political correctness and callous disregard for human life. But I digress. We’re on a pub crawl of Hemingway bars here, right? 

Then to Sloppy Joe’s

The second of the Hemingway bars on this pilgrimage is the current Sloppy Joe’s, a much bigger and more crowded establishment. Here a younger, louder guitarist plays more modern songs like “Into the Dark.”  That place sells more than just drinks. You can eat a Sloppy Joe, which I did. Apparently this bar was the creator of that well-known, to people my age, school cafeteria staple of the same name. You can also get fish sandwiches. My husband had one of these and said it was quite good. And there is a gift shop in this more commercial of Hemingway bars with t-shirts, and mugs, and go-cups. In the main dining room, Hemingway looks down from a framed picture of himself in a fisherman’s sweater. In his gaze are a boisterous company of loud tourists eating and drinking. Waiters wear beards and ball caps.  In other words, they all are a caricature of Hemingway in the most famous of Hemingway bars. On one wall is a picture of a bunch of men who look superficially like Hemingway, but clearly are not him. When I ask about it, I find that it’s the Hemingway-look-alike hall of fame.  Last year 149 men came to compete. I am astounded that it’s so many.

Finally to the Hemingway House Museum

When I tell this to my husband, he snorts. “It’s the only time you can get any positive attention for looking like a fat middle aged guy,” he says. He buys me the t-shirt. We get going to the Hemingway House museum. Hemingway bars, I suppose, are all over the world, but we had done the Key West versions.

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