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

Hemingway Days in Key West celebrates the literary success and lifestyle of Ernest Hemingway, one of America’s most famous writers. Every year, to honor Hemingway’s birthday, Key West comes to life with lively literary events. During Hemingway Days, locals, visitors, and fans celebrate Hemingway with a look-a-like contest, poetry readings, and a three-day marlin tournament.

July 23-27, 2025

Hemingway spent much of the 1930s living on Key West. His home, where he wrote many of his best-known works, including Death in the Afternoon and To Have and Have Not, is now a landmark museum on Whitehead Street across from the lighthouse. Visiting Key West for Hemingway Days gives you a special glimpse inside our rich literary heritage.

Hemingway Look-Alike Contest

The Annual Hemingway® Look-Alike contest is held at Sloppy Joe’s Bar, a common hang out spot for the author while he was living in Key West. The contest attracts more than 100 participants and is hosted by the Hemingway Look-Alike Society. The contest is no joke — it has two rounds of competition before the finals are held. Grab a seat to watch or just join in on the after party as it spills over into the streets.

Happening Throughout the Event

Lorian Hemingway Short Story Competition. The competition started in 1981 and has awarded over $70,000 to writers of merit. More information may be found at www.shortstorycompetition.com.
Daily Tours of the Hemingway Home & Museum at 907 Whitehead Street. Visit https://www.hemingwayhome.com for more information.
July 23-27, 2025, the Key West Marlin Tournament, offering cash prizes for top catches of marlin and other fish, attracts up to 75 registered boats and their crews. The tournament, held Wednesday through Saturday during the annual Hemingway Look-Alike Contest, is a world-class fishing event hosted at the Perry Hotel and Marina in the Lower Keys. More information is available at www.keywestmarlin.com.
Saturday, July 20, 7:30 pm: Hemingway 5K Sunset Run and Paddleboard Races (5K Sunset Race by Key West Half Marathon).

WEDNESDAY, JULY 23, 2025

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 24, 2025

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) View Contest Results

FRIDAY, JULY 25, 2025

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) View Contest Results

SATURDAY, JULY 26, 2025

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. View Contest Results

SUNDAY, JULY 27, 2025

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.

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.

Join us for an unforgettable event where the spirit of Ernest Hemingway is alive and well, and the essence of Key West’s fun-loving culture is on full display. We can’t wait to see you here!