Annual Hemingway Days in Key West, Florida

Anybody else read Hemingway in High School? You know… “The Old Man and the Sea” and “For whom the Bell Tolls”. If you loved the books as I did, then this is a must-do, at least once in your life. Hemingway Days in Key West celebrates the amazing man, author, and fisherman, Hemingway was.

Every July a group of beaded men descends on Key West, in hopes of winning the Ernest Hemingway Look-alike contest. Fans of Hemingway follow. This annual event celebrates the Nobel prize-winning author’s achievements and his true love of Key West and its easy-going lifestyle.

street fair during hemingway days


There are many events to choose from. Watching the look-alike contest, participating in the Three Day marlin fishing tournament, watching the “Running of the Bulls”, a street fair, a 5k run, and paddleboard race, and event a short story competition.

At Sloppy Joe’s Bar, you can see … and maybe participate??… in the look-alike contest. Each year bearded men walk across the stage and are judged by the previous winners all trying to win the title of “Papa”. There are preliminary rounds where you can see all the different versions of Hemingway. Stick around for the final round and cheer for your favorite.

Why Sloppy Joe’s? Well, it was a frequent hangout of Ernest when he lived in Key West during the 1930’s. Be sure to stop by and see the place. It offers great drinks, food, and music, all throughout the year. And… it’s located on the famed Duval Street, so you won’t miss any of the action.

Sloppy Joe’s Bar, a Drink and a Place at the End of the World

Hemingway in Key West

It was a fateful turn of events that led to Ernest Hemingway living in Key West. His car, ordered by his wife’s uncle was late. This gave Ernest the opportunity to explore the island and, like all of us, he quickly fell in love and did not want to leave.

He and his wife, Pauline, eventually bought the home on Whitehead Street and settled in. Well, actually she began an extensive remodel. Be sure to plan a trip to the Ernest Hemingway Home. See the six toed cats, and tour the grounds. Take the tour and hear the story about the penny by the pool.

See his small studio behind the home. Here is where he wrote some of his best known works, like “For Whom the Bell Tolls” and “To Have and Have Not”. Did you know “To Have and Have Not’ is the only Hemingway novel based in the United States? It’s based on his good friend and Sloppy Joe’s bar owner Joe Russell.

Learn more about the Ernest Hemingway Home

True fans of Ernest Hemingway appreciate his taste in drinks and fun. After exploring the Hemingway Home, hop across the street to the Lighthouse Court bar. There, ask for the Hemingway daiquiri. You won’t be disappointed.

The author Ernest Hemingway lived in Key West from 1931 to 1939. During that time he had a great impact on the island and its literary scene. During this time he wrote:

  • “Death in the Afternoon”
  • “The Green Hills of Africa”
  • “The Fifth Column”
  • “The snows of Kilimanjaro”
  • “The Short Happy Life of Francis Macomber”
hemingway look alikes

Contests and Wacky Fun

There is a short story contest coordinated by Ernest Hemingway’s granddaughter. Are you a budding author? Check out the Lorian Hemingway short story competition and plan to enter you might win one of the cash prizes. There is a small entry fee, but who knows you might win.

Love to learn more about Hemingway, aside from the tour of his home? The Custom House usually has a display about Hemingway in Key West. Great insights into his life and how he enjoyed Key West.

Did you know Hemingway won a Pulitzer prize for the “Old Man and the Sea”? Today, at the Custom House, the Historical Society has a museum exhibit of the Guy Harvey drawings depicting this awarding-winning novel.

Head over to the corner of Greene Street and Duval St. Here you will watch the “Running of the Bulls”. It’s a spookfon the running of the bulls event in Pamplona, Spain. The bearded Hemingways “run” manmade fake bulls around the block and then offer photo opportunities. This wacky event is a lot of fun.

Love to fish? Try your hand at the three-day marlin tournament. You can fish for marlin, spearfish, sailfish, tuna, dolphin, and wahoo and maybe even win a cash prize.

Marlin Tournament Information

Our first Annual Hemingway Days festival we attended was amazing. We took in all of the events and even ran the 5k. A sunset run through Key West ending at the Southernmost Point is amazing. Of course, being able to have a few beers at the end, makes it that much better.

Add this popular event to your calendar, it’s so much fun! It’s an annual celebration to honor the late writer, his literary greatness, and, of course, his birthday on July 21.

The Hemingway Days schedule.

hemingway days photo opportunity

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