News | July 3, 2025

Hemingway Days Celebration in Key West

Andy Newman/Florida Keys News Bureau

On his tenth attempt, David 'Bat' Masterson celebrates his 2024 victory with past winners of the Hemingway Look-Alike Contest outside Sloppy Joe's Bar in Key West.

The annual Hemingway Days which honors Nobel Prize-winning author Ernest Hemingway will be held July 23-27 at his Key West home.

At the heart of the festivities is the Hemingway Look-Alike Contest, now in its 44th year. Held July 24-26 at Hemingway's favorite watering hole, Sloppy Joe’s Bar, the contest brings together dozens of entrants from around the globe. Competition is also keen for another of the signature events, the Running of the Bulls on July 26 in which instead of live animals, participants race with handmade wooden "bulls" down Greene Street.

Other highlights include:

  • the Lorian Hemingway Short Story Competition founded by Hemingway's granddaughter to honor emerging writers
  • tours of the Hemingway Home & Museum including his famous writing studio and cats
  • Key West Marlin Tournament (July 23-26) hosted at the Perry Hotel and Marina in the Lower Keys bringing together world-class anglers for a fishing challenge
  • an interactive Hemingway Feast on July 24 with traditional Key West dishes from Hemingway's era at the Key West Cooking School
  • the Hemingway 5K Sunset Run on July 26, followed by rum tastings on the sand at Outside Southernmost Beach Café 
  • a Caribbean Street Fair (July 26) on Duval Street
  • Papa Birthday Bash and Hemingway Rum Bar Stroll (July 27) at Sloppy Joe’s with a rum bar stroll to eight locations

"Whether you're a writer, a reader, a Hemingway enthusiast, or simply seeking an unforgettable summer celebration, Hemingway Days 2025 offers a one-of-a-kind mix of history, humor and community,” said Donna Edwards, Sloppy Joe’s Brand Manager.