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.
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.
“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 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 features dozens of stocky, bearded “Papas” from around the globe, each hoping to become the next official Hemingway double. 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 the group lives up to its 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 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 beards & 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 daily tour of Papa’s Key West home, including his famous writing studio (and even more famous cats).
A Hemingway Feast (Thursday, July 24): Savor traditional Key West dishes from Papa’s era — and learn to prepare them — during an 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 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 celebration of local artisans, food and community spirit.
Papa Birthday Bash + Hemingway Rum Bar Stroll (July 27): Close out the festivities with Bloody Marys, 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.
