Key West Is a Literary Pilgrimage for Fans of Hemingway

Ernest Hemingway is one of the greatest writers in U.S. history. Born in 1899 in Oak Park, Illinois, the author of classics like “The Sun Also Rises” and “The Old Man and the Sea” moved frequently throughout his lifetime. He lived in cities around the world, including Paris, France; Madrid, Spain; and Havana, Cuba, and traveled extensively as a war correspondent and journalist. But perhaps no other city is as fiercely proud of its Hemingway connection as Florida’s Key West. The southernmost city in the contiguous U.S. was the writer’s home for eleven years, from 1928 to 1939. His legacy can still be felt throughout the city, making it an essential literary destination in Florida. 

Why This Destination Is Perfect for Hemingway Fans

Hemingway’s influence in Key West is so strong that it would be difficult to avoid hearing about the writer while visiting the island. The house he lived in with his second wife, Pauline, is now the Hemingway Home and Museum. Hemingway fans travel from all over the world to visit the beautifully preserved property and get a glimpse into the novelist’s private life. Besides bedrooms and family rooms, you can go into the writer's studio, where he worked on masterpieces like “To Have and Have Not” and ”For Whom the Bell Tolls.” While the house is great, the best part about the museum is seeing the true owners of the property roam around their kingdom: the six-toed cats that are direct descendants of Hemingway’s beloved Snowball. 

Hemingway's former home isn't the only spot in Key West connected to this literary giant. Sloppy Joe’s, a classic bar, is where the author spent a lot of his leisure time hanging out with friends like playwright Tennessee Williams. It’s also where he met his third wife, legendary war correspondent Martha Gellhorn. The bar eventually moved location, and Capt. Tony’s Saloon replaced it. Both are still open and regularly welcome Hemingway fans. Similarly, you can visit Blue Heaven. While now known for its generous Key lime pie, the restaurant was once a saloon where Hemingway acted as a referee for amateur boxing fights. Although you won’t find a semblance of its former life, it’s still interesting to be in a place that was once so important to the writer — and to get some darn good pie while you’re at it.

Tips for Planning Your Literary Pilgrimage

If you’re a huge Hemingway fan, plan your Key West trip for the end of July. Every year, the city hosts Hemingway Days, a celebration that coincides with the author’s birthday on July 21. The signature event is the Hemingway Lookalike Contest held at the new Sloppy Joe’s location. Bearded men do their best “Papa” impressions as the community cheers them on. It’s a lot of fun, even if you haven’t yet gotten around to reading any of the writer’s work. 

Those wanting to stick with a literary theme should stay at La Concha, a 1926 hotel that the author frequented during his time in Key West, and where Tennessee Williams stayed while finishing “A Streetcar Named Desire.” Besides the Hemingway-related spots, make sure to visit Books and Book @ The Studios Of Key West, a small bookshop co-founded by Judy Blume, another popular American writer.

Feeling inspired? Try planning your own trip using Only In Your State’s itinerary planner.