Schedule of Events

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 23-26, 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 26, 7:30 pm: Hemingway 5K Sunset Run (5K Sunset Race by Key West Half Marathon).

SUNDAY, JULY 20, 2025

• 2:00 – 4:00 pm: 5th Annual Papa’s Pilar Cocktail Classic – Taste some of the best cocktails in the Keys, made by the best mixologists. Watch, taste, and enjoy while 12 TOP Mixologists compete for Best of Show and to WIN some incredible prizes, with a portion of proceeds to benefit MARC HOUSE.  See the Pilar event page for more details.

TUESDAY, JULY 22, 2025

• 5:00 – 7:00 p.m.: Welcome to Key West Papa’s (Papa’s and wannabes and family) Happy Hour at Hemingway Distillery, 201 Simonton Street. Welcome cocktail on Papa’s Pilar for all Lookalikes, featuring special cocktails. 

WEDNESDAY, JULY 23, 2025

• 1:00 – 3:00 p.m.: Pre-Contest Happy Hour @ Hemingway Social Club, 201 Simonton Street.  
• 5:00 – 7:00 p.m.: 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

• 11 a.m. – 1 p.m.: “A Hemingway Feast” at the Key West Cooking School, 291 Front St. upstairs. Savor traditional Key West dishes from Papa’s era — and learn to prepare them — during an entertaining, interactive experience at the island’s newest attraction for foodies. The learn-and-dine adventure even features “grits-n-grunts,” mentioned in Hemingway’s Key West novel “To Have and Have Not.” Advance booking required; visit keywestcookingschool.com and use the code “PAPA10” for a $10 discount (valid only for the 11 a.m. event on July 24). 
• 1:00 – 3:00 p.m.: Bottle & Book Signing of “Dear Papa” at the Hemingway Social Club, 201 Simonton 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.
• 5:30 p.m.: Introduction “Welcome” to the Contest by David Douglas, president of the Hemingway Look-Alike Society & Jeff Allen, CEO of Sloppy Joe’s.
• 6:10 p.m.: 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 p.m.: 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 HLAS Scholarship Fund immediately following preliminary round-one while awaiting results) View Contest Results

FRIDAY, JULY 25, 2025

• 1:00 p.m.: 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 p.m.: Round Two Contestants Check in at the registration table to pick up the name tag and event shirt.
• 6:30 p.m.: 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) View Contest Results

SATURDAY, JULY 26, 2025

• 10 a.m. to 10 p.m.: (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 p.m.: 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 p.m.: Finalist Contestants must check in at the registration table at Sloppy Joe’s.
• 6:30 p.m.: Sloppy Joe’s 44th Annual Hemingway® Look-Alike Contest – FINAL ROUND with the ‘crowning’ of Papa 2025. (Live Auction benefiting the HLAS Scholarship Fund immediately following the final round, while awaiting results. View Contest Results

SUNDAY, JULY 27, 2025

• 9:00 a.m. – 1:00 p.m.: Papa Birthday Bash at Sloppy Joe’s – Bloody Marys with Papas (cash bar), Photo Opportunities with Papa 2025 & Papa birthday cake at noon.
• 12:00 p.m.: Key West Beach N’ Beer Mile! The Beach N’ Mile bib has four beer tickets on your bib. This casual and fun beer mile takes place on the beach at the Southernmost Beach Cafe, located at 1405 Duval Street, and the event begins at noon. Look for the Key West Half Marathon sail flags and cones! Costumes are encouraged, and we will be giving various prizes out for the best costumes.
• 3:00 – 6:00 p.m.: Pool Party at The Backyard Pool and Social Club | Blue Flamingo Resort, 3280 N. Roosevelt Blvd.