Key West Sets 'Hemingway Days'

Credit: Florida Keys and Key West

(Press Release) KEY WEST, Fla. (June 30, 2025) — Fans of literature, adventure and offbeat fun are invited to experience one of Key West's most beloved annual events — Hemingway Days. From July 23-27, 2025, this whimsical celebration will honor the timeless legacy of Nobel Prize-winning author Ernest “Papa” Hemingway, who once called the island his home and creative haven. 

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Hemingway famously said of Key West, “It's the best place I've been anytime, anywhere.” And Hemingway Days is the perfect time to find out why, as the destination pays jubilant tribute to one of America's most celebrated authors. 

“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. 

From literary readings to zany street spectacles, Hemingway Days reflects both the adventurous spirit and literary genius of the man himself. At the heart of the festivities is the beloved Hemingway Look-Alike Contest, now in its 44th year. Held July 24-26 during Hemingway Days at Hemingway's favorite watering hole, the legendary Sloppy Joe’s Bar, the contest brings together dozens of stocky, bearded “Papas” from around the globe, each hoping to become the next official Hemingway double. Check out the entry form to find out if you’ve got what it takes. Papa 2025 will be crowned at Sloppy Joe’s on Saturday, July 26 at 6:30 p.m. 

“The Hemingway Look-Alike Society’s first rule is “have fun,” and this group knows how live up to this philosophy. Our most senior Papa judging the Look-Alike Contest is Fred Johnson who won in 1986.  Many contestants return year after year to compete (some for over 30 years). This event has created an extended family for many who return each July to celebrate and have fun,” said Edwards.  

Other signature events include the light-hearted Running of the Bulls on Saturday, July 26, where instead of live animals, participants race with handmade wooden "bulls" down Greene Street. It's a hilarious nod to Hemingway's affection for Spanish traditions, reimagined with classic Key West flair. 

Beyond Facial Hair and Fake Bulls 

• The Lorian Hemingway Short Story Competition: Founded by Hemingway's granddaughter, this event honors emerging writers and continues the family's literary legacy.  
• Hemingway Home & Museum: See the world through Hemingway’s eyes on a fascinating daily tour of Papa’s Key West home, including his famous writing studio (and even more famous cats).    
• Key West Marlin Tournament (July 23-26): Hosted at the Perry Hotel and Marina in the Lower Keys, this event brings together world-class anglers for  an exhilarating fishing challenge that pays tribute to Hemingway's passion for  the sea.  
• A Hemingway Feast (Thursday, July 24): Savor traditional Key West dishes from Papa’s era — and learn to prepare them — during an entertaining, interactive experience at the Key West Cooking School, the island’s newest attraction for foodies.   
• Hemingway 5K Sunset Run (July 26): Active attendees take a scenic run, followed by a breathtaking Key West sunset and rum tastings on the sand at Outside Southernmost Beach Café.   
• Caribbean Street Fair (July 26): This lively market turns Duval Street into a colorful celebration of local artisans, food, and community spirit.  
• Papa Birthday Bash + Hemingway Rum Bar Stroll (July 27): Close out the festivities with Bloody Mary’s, birthday cake and photo ops with Papa 2025 at Sloppy Joe’s. Then, go on a rum bar stroll to eight locations, with a Papa’s Pilar Rum drink waiting at each stop.  

For a full schedule of events, go to hemingwaydays.com. ​