Hemingway® Look-Alike Contest July 17-21, 2024

The Hemingway Look-Alike Contest in Key West is an annual event with the contest taking place over several days. This is a fun filled affair with participants from around the world. Let’s see who resembles the famous writer this year! We will be continue to offer boat rentals & charters during this fun and exciting event. For boat rentals click here and charters click here. 

Check out this fun schedule available through Sloppy Joe’s restaurant & bar: 

WEDNESDAY, JULY 17, 2024

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

THURSDAY, JULY 18, 2024

• 9:00 -10:00 a.m.: “Coffee and Donuts with the Papas.” Meet the contestants and previous winners of the “Papa” Hemingway® Look-Alike Contest at the Southernmost Pint Brewpub located at 522 Front Street.
• At 5:00 p.m., Round One check-in contestants must check in at the registration table to pick up their name tags and event shirts.
• 5:10 pm: Achievement Award Presentation.
• 5:30 pm: Introduction “Welcome” to the Contest by David Douglas & Jeff Allen.
• 6:00 pm: Introduce “Bahama Bob” to sing our National Anthem.
• 6:10 pm: Hemingway Look-Alike Society Scholarship Presentations. The society will 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 43rd 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 HLAS Scholarship Fund immediately following preliminary round-one while awaiting results)

FRIDAY, JULY 19, 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 Company docks, 631 Greene Street.  Free to watch. (Silent Auction benefiting the HLAS Scholarship Fund during Fish-Off)
• 5:00 pm: Round Two Contestants Check in at the registration table to pick up the name tag and event shirt.
• 6:30 pm: Sloppy Joe’s 43rd 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 20, 2024

• 10 am to 10 pm: (Duval Street closure ) Caribbean Street Fair to benefit Literacy Volunteers of America (LVA) Monroe County, Inc. Key West’s annual Hemingway Birthday Celebration provides an excellent opportunity for Florida’s artisans and food vendors to display and sell their works during the one-day Caribbean Street Fair on world-renowned Duval Street.  If you are interested in being a vendor, download the vendor application.
• Noon: Photos with “Papas.” Hemingway® Look-Alikes, Wannabes, and Bulls provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s.
  • HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturdays. Those wishing to wear traditional white clothing with a red sash need to be prepared and bring their own clothing (these items are not sold).
• 1:00 pm: Annual ‘Running’ of the Bulls. This wacky event, sponsored by Sloppy Joe’s Bar, features past “Papa” Hemingway® Look-Alike Contest winners 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.
• 5:30 pm: Finalist Contestants must check in at the registration table at Sloppy Joe’s.
• 6:30 pm: Sloppy Joe’s 43rd Annual Hemingway® 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 results.

SUNDAY, JULY 21, 2024

• 9:00 am – 1:00 pm: Papa Birthday Bash at Sloppy Joe’s – Bloody Marys with Papas (cash bar), Photo Opportunities with Papa 2024 & Papa birthday cake at noon.
• 12:00 – 4:00 pm: Hemingway Rum Bar Stroll presented by Papa’s Pilar Rum.  Includes 8 locations with a Papa’s Pilar Rum drink at each location. The entry fee is $49 and includes a Rum Stroll Race t-shirt.

Sloppy Joe’s bar
Phone: 866-517-8833

photo credit by Pixaby