Look-Alike Schedule

Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest July 23-27, 2025

WEDNESDAY, JULY 23, 2025

5:00-7:00pm: Meet & Greet w/the “Papas” at Sloppy Joe’s. Get to know the contestants and previous winners of “Sloppy Joe’s Hemingway® Look-Alike Contest.

THURSDAY, JULY 24, 2025

9:00 am – 10 am: Donuts & Coffee with the Papas location to be determined

5:00 pm: Round One contestants need to check in at registration table to pick up name tag and event shirt.

6:10 pm: Hemingway Look-Alike Society (HLAS) Scholarship Presentations. The society is to announce the winners of its annual scholarships for The College of the Florida Keys students. On stage at Sloppy Joe’s Bar.

6:30 pm: Sloppy Joe’s 44th Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round.

Live Auction benefiting the Hemingway Look-Alike Society’s Scholarship Fund to begin immediately after Preliminary Round One while awaiting results.

FRIDAY, JULY 25, 2024

1:00 pm: Papa Hemingway Look-Alike Fish-Off. Cheer your favorites as the Papas & Wannabes compete in this dockside catch-and-release challenge using traditional “Cuban Yo-Yos” at Conch Republic Seafood Co. docks, 631 Greene Street. Free to watch. (Silent Auction benefiting the HLAS Scholarship Fund during Fish-Off).

5:00 pm: Round Two contestants need to check in at registration table to pick up name tag and event shirt at Sloppy Joe’s.

6:30 pm: Sloppy Joe’s 44th Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round. (Live Auction benefiting the HLAS Scholarship Fund immediately following Preliminary Round Two while awaiting results.)

SATURDAY, JULY 26, 2025

10 am to 10 pm: Literacy Volunteers of America Monroe County’s Caribbean Street Fair on Duval Street.

Noon: Photos with “Papas.” Get your photo taken with Papas, Wannabes, and the bulls at this year’s Hemingway® Look-Alikes Contest. Greene Street outside Sloppy Joe’s.

1:00 pm: Sloppy Joe’s Annual ‘Running’ of the Bulls. This wacky event features past “Papa” Hemingway® Look-Alike Contest winners and Wannabes dressed in their Pamplona best — and a breed of “bull” found only in Key West. The fun takes place on Greene street outside Sloppy Joe’s. *HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturday. Those wishing to wear tradition white clothing with red sash need to be prepared and bring their own clothing (these items not sold).

5:30 pm: Finalist contestants need to check in next to stage.

6:30 pm: Sloppy Joe’s 44th Annual Hemingway® Look-Alike Contest – FINAL ROUND to announce Papa 2025. (Live Auction benefiting the HLAS Scholarship Fund immediately following the final round while awaiting results)

SUNDAY, JULY 27, 2025

9:00 am – 1:00 pm: Papa Birthday Bash at Sloppy Joe’s! Bloody Marys with Papas (cash bar), Photo Opportunities with Papa 2025, and Papa Birthday Cake at noon.

For Sloppy Joe’s Look-Alike Event information email [email protected]