Ernest Hemingway Hang Outs in Key West

Pretty much anyone who knows anything about Key West knows that Ernest Hemingway once called the island home. He is arguably the most famous Key West resident of all time, hence the huge annual Hemingway Days celebrations held each July in honor of his birthday.

In the 1930’s when he resided on the island, Ernest Hemingway, or as the locals came to affectionately call him, Papa, became a major tourist draw to the island. People were always trying to get into his home to get a look at the famed author. Well, almost 100 years later, his spirit is still a huge draw for tourists.

Some of the places that Hemingway used to spend time at on the island no longer exist, and some are private residences, so we will leave those off of this list. But there are many places that Hemingway aficionados can still visit and walk were he once did. Here are some of those places for you to check out.

The Ernest Hemingway House and Museum – This is the obvious place for Hemingway fans to congregate; he lived in this house for most of the 1930’s with his second wife, Pauline. See what he was surrounded by and where he slept and wrote. Maybe you will be inspired! Plus, the can pet the descendants of Hemingway’s famed six-toed cats.

Sloppy Joe’s Bar – While Hemingway did indeed hang out at the original Sloppy Joe’s Bar which was located just across the street from the current location, it is still a fun place to visit and load up on some souvenirs to commemorate your visit. Plus, some of Hemingway’s actually belongings are housed here as he left many things here when he moved in 1939.

Capt. Tony’s Saloon – This is the location of the Original Sloppy Joe’s Bar and the actual place that Hemingway actually spent a lot of his time with pals while in Key West.

Blue Heaven – While Hemingway was not having a delicious brunch here like we can today, he could often be found on the grounds boxing and reffing matches after Pauline got rid of the boxing ring they had in their yard. Where else was she supposed to build her saltwater pool?

Casa Antigua / Key West Escape Room – This is the first property that Hemingway stayed at in Key West. Formerly a car dealership where he was picking up a car; the delay allowed time for him to fall in love with the island. He stayed in the upstairs hotel until the car was delivered.

La Conch Hotel – This was actually called the Key West Colonial Hotel in Hemingway’s day. He and Pauline had family and friends stay here and they often spent time here visiting as well.

St. Mary’s Star of the Sea – Hemingway converted to Catholicism for his second wife, Pauline, and together they would attend mass here on Sundays.

The waters surrounding Key West. Hemingway was a man’s man and he loved fishing and being on the water. He even used his boat, the Pilar, to patrol the waters for German submarines. You can take a fishing charter and experience one of the activities that Hemingway so loved.

The Key West Historical Memorial Sculpture Garden located in Mallory Square has 36 bronze busts of people chosen by a committee to be the most influential people who have resided in Key West. Hemingway and his friend, charter boat captain Edward “Bra” Saunders, are among those commemorated here. The garden is located in Mallory Square on the corner of Wall Street and Tifts Alley. Look between the Key West Chamber of Commerce and El Meson de Pepé restaurant. 

The Custom House Museum has a permanent exhibit focused on Hemingway’s life in and impact on Key West. Also on display are a few cases of his personal items. There are also often temporary exhibits at the Customs House related to Hemingway and during our visit there was a series of 59 original pen-and-ink drawings by marine wildlife artist Guy Harvey that depict the storyline of Ernest Hemingway’s novel, The Old Man and The Sea. A great way to learn more about Hemingway in Key West and more generally about the interesting history of the city.

For more about Key West…

There are so many different places to eat in Key West. Before you decide where to go, be sure to read our Key West restaurant reviews; check out our restaurant review section of this blog.

To see what is happening on the island during your visit, check out our Key West Events Calendar to see other upcoming special events.

And for more information about the fun side of Key West… things to do and see in our island city, go to our Key West Web Site.

Feel free to Email Me if you have any questions about Key West!!

Island Genn – Your Key West Concierge

About the author: Island Genn

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