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Hemingway’s Key West

Posted on: March 13th , 2018 | History
Hemingway’s Key West

The stately Hemingway House on Whiteland Street in Old Town is a big draw for tourists visiting Key West. The island has changed dramatically since Ernest Hemingway arrived with his wife in 1928. The addition of New Town doubled the size of the island and the U.S. embargo on Cuba forever changed Key West.

Despite the changes, Hemingway’s mark on the island hasn’t washed away to sea. To see Key West beyond the author's home, check out these spots and activities to see why Papa Hemingway visited the island on a whim and ended up living there for more than a decade.

Blue Heaven


Located just a block from the Hemingway Home and Museum, Blue Heaven is an iconic landmark in its own right. In the 1930s it hosted Friday night boxing matches in its outdoor courtyard and Hemingway was the designated referee. Today, Blue Heaven is an island favorite for its Caribbean-Florida cuisine and excellent brunches (lobster benedict, anyone?). Don’t miss a meal on their outdoor patio, which still maintains the wild Key West feel of free-range roosters and cats. 729 Thomas Street

Captain Tony’s Saloon

Originally opened as an icehouse, Captain Tony’s has been a cigar factory, saloon and morgue. This was the original site of Sloppy Joe’s in the time of Hemingway, but later relocated due to a rise in rent. It’s believed that Hemingway passed many evenings in this watering hole between 1933-1937, even writing about it in his novel To Have and Have Not. Check out the dive bar frequented by locals any evening for live music and an ice cold beer. 428 Greene Street

Take a Trip Sport Fishing

Hemingway fell in love with deep-water sport fishing after moving to Key West and often ventured out to Bimini, Cuba and Dry Tortugas in search of a big catch. He also set the record in 1938 for catching seven marlins (or was it 8?). We suggest you check out KW charter services for sport fishing, or talk with our front desk to make accomodations. To plan a trip to Dry Tortugas, check out our day guide.

Sloppy Joe’s


Hemingway was good friends with bar owner and boat captain Joe Russell, though much controversy surrounds the author's favored drink spot. Regardless, Hemingway wouldn’t turn up his nose to a drink, and neither should you. Sloppy Joe’s on Duval Street is always busy, efficiently managed and teeming with energy. Stop by for food and a drink and get a t-shirt with the author’s face on it. 201 Duval Street

Custom House Museum

The Key West Art & Historical Society Custom House Museum wasn’t a Hemingway Haunt, but today it houses a neat little exhibit of the author, including his typewriter, Red Cross uniform and other items. Checkout local history and artifacts at the Custom House, located near Mallory Square. 281 Front Street

Hemingway Days Festival

This annual event always falls on the author’s birthday, July 21, and hosts both a look-alike and arm-wrestling contest, a bizarre bull run and other fun events on Duval Street. Old Town teeming with Hemingway lookalikes is a site to behold. If you’re visiting us in July you can't miss it. More info here.


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