45th Annual Hemingway Look-Alike Contest in Key West
When: July 21 - July 26, 2026
Where: Sloppy Joe’s Bar, 201 Duval St, Key West, FL 33040
The 45th Annual Hemingway Look-Alike Contest and Festival takes place July 21–26, 2026, celebrating the life, literary legacy and adventurous spirit of Ernest Hemingway. The main contest activities begin Wednesday, July 22, and continue through Sunday at Sloppy Joe’s Bar and several locations around Key West.
The Papas gather at Sloppy Joe’s for a Meet & Greet from 5:00–7:00 p.m. Wednesday. Preliminary Round One of the Look-Alike Contest begins at 6:30 p.m. Thursday, followed by Preliminary Round Two at 6:30 p.m. Friday. Both rounds include scholarship fundraising auctions while the results are determined.
Saturday’s festivities include the Caribbean Street Fair on Duval Street from 10:00 a.m.–10:00 p.m., Photos with the Papas at noon and the playful Running of the Bulls at 1:00 p.m. on Greene Street. The Look-Alike Contest Final Round begins at 6:30 p.m. inside Sloppy Joe’s, where the winner will be crowned “Papa 2026.”
The celebration concludes Sunday with the Papa Birthday Bash from 9:00 a.m.–1:00 p.m. at Sloppy Joe’s, including photo opportunities with Papa 2026 and birthday cake at noon. Additional festival activities include Hemingway-themed films, cocktails, museum exhibits, fishing events, literary programs and the Papa’s Tales Storytelling Competition.
The complete official schedule is available from the Hemingway Look-Alike Contest.
Verified start date: Tuesday, July 21, 2026
Main contest dates: Wednesday, July 22–Sunday, July 26, 2026
Location: Sloppy Joe’s Bar, 201 Duval Street, Key West, FL 33040
Website: https://keywestlookalikes.com/
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