2025 Contest Schedule
Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest July 23-27, 2025
WEDNESDAY, JULY 23, 2025
5:00 pm-7:00 pm: Meet & Greet w/ the Papas. Get to know the previous winners of the Papa Hemingway® Look-Alike Contest and this year’s Look-Alike Contestants at Sloppy Joe’s.
THURSDAY, JULY 24, 2025
9:00-10 am: Donuts & Coffee with the Papas @ Southernmost Pint Brewpub located at 522 Front St.
5:00 pm: Thursday night Contestants must check in at the registration table.
5:10 pm: Achievement Award.
5:30 pm: Introduction “Welcome” to the Contest from by David Douglas & Jeff Allen
6:00 pm: Introduce “Bahama Bob Leonard” to sing our National Anthem.
6:10 pm: Scholarship Presentations.
6:30 pm: Sloppy Joe’s Look-Alike Contest Preliminary Round One (LIVE AUCTION benefiting the HLAS Scholarship Fund immediately following preliminary round-one while awaiting results).
FRIDAY, JULY 25, 2025
1:00 pm: Papa Hemingway Look-Alike Fish-Off. Cheer your favorites as the Papas & Wannabe’s 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: Friday night Contestants must check in at the registration table.
6:30 pm: Sloppy Joe’s Look-Alike Contest Preliminary Round Two (LIVE AUCTION benefiting the HLAS Scholarship Fund immediately following preliminary round-two while awaiting results).
SATURDAY, JULY 26, 2025
10 am-10 pm: Hemingway Days Caribbean Street Fair (Duval Street).
12’ Noon: Get your photo taken with Papas, Wannabe’s, and bulls at this year’s Look-Alike Contest.
1:00 pm: Sloppy Joe’s Annual ‘Running’ of the Bulls. On the ‘running of bulls,’ Hemingway once remarked, ‘Pamplona is no place to bring your wife.’ Not the case here. There are no young Spaniards, just Papa’s making the mock run in the streets. Ha! We do actually have young Papa Wannabe’s making the run.
5:00 pm: Finalist Contestants must check in at the registration table.
6:30 pm: Sloppy Joe’s Look-Alike Contest FINAL Round with the “crowning” of Papa 2024
(LIVE AUCTION benefiting the HLAS Scholarship Fund immediately following the final round while awaiting the results of Papa 2024.
SUNDAY, JULY 27, 2025
9:00 am– 1:00 pm: Bloody Marys with Papa at Sloppy Joe’s, Photo opportunity with Papa 2024.
12:00 pm: Papa Cake presentation and cutting of the Birthday cake.
To discover more about the Hemingway Look-Alike Contest, the auction, and other complementary events, please visit the event website, KeyWestLookAlikes.com
If you would like to enter the Hemingway Look-Alike Contest, you can now submit your registration directly from the Sloppy Joe’s Bar website, or you can download the printed entry form below.
For Sloppy Joe’s Look-Alike Event information email donna@sloppyjoes.com