The Papas Are Back: Hemingway Hopefuls Return to Key West

FLORIDA KEYS VIDEO ADVISORY       July 24, 2026 

Contacts: Chad Newman, Chad@fla-keys.com (310) 283-8441 or Mary B. Haban, Mary@fla-keys.com (305) 394-3142 

Story: The Papas Are Back: Hemingway Hopefuls Return to Key West 

Locator: Key West, Fla. 

Usage: HANDOUT / RIGHTS CLEARED (Unlimited Broadcast & Digital) 

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Photo Captions Below 

Video: B-roll from the opening preliminary round of Sloppy Joe's 45th Annual Hemingway Look-Alike Contest at Sloppy Joe's Bar in Key West, Fla., on July 23, 2026. Visuals include contestants crossing the stage, longtime competitors greeting one another, audience reaction, judging by past winners and crowd support for would-be "Papas." 

Technical Data: 

     TRT: 1:53 

     Filename: HemingwayLookAlikeRoundOne.mp4 

     Audio: Nat. Sound - Stereo Mix 

Credit: Florida Keys News Bureau (Screen credit appreciated, not mandatory) 

NOTE TO EDITORS/PRODUCERS: The Florida Keys News Bureau plans additional Hemingway Days video coverage: 

Saturday, July 25: Coverage of Key West's 1 p.m. "Running" of the Bulls outside Sloppy Joe's Bar. Inspired by the renowned run in Pamplona, Spain, the Key West version features costumed Hemingway look-alikes parading with manmade bulls on wheels. 

Sunday, July 26: Coverage of Saturday night's final round of the Hemingway Look-Alike Contest and the crowning of "Papa 2026." B-roll and a SOT with the winner are planned. 

The Papas Are Back: Hemingway Hopefuls Return to Key West 

KEY WEST, Fla. (July 24, 2026) — In most places, wearing a thick wool sweater in the dead of summer may raise a few eyebrows. In Key West, it's all part of the “uniform.” 

White beards, broad smiles and a carefully crafted swagger. That’s what rolled into one of Key West’s most legendary bars Thursday night, as the opening round of the 45th Annual Hemingway Look-Alike Contest got underway at Sloppy Joe’s. 

Contestants took the stage at the Duval Street saloon, the very place Ernest Hemingway used to hang out during the 1930s while living in Key West. 

Some rocked safari attire. Others...his iconic fisherman sweaters. But nearly all brought those signature beards, bravado and the brave face needed to convince a panel of past winners that they were worthy of advancing to the final round. 

The “hopefuls” were judged on more than their physical resemblance to Hemingway. They also considered how well they captured the “Papa” persona (as Hemingway was affectionately called), their stage presence and ability to win over the room. 

When the night was over, twelve contestants advanced to Saturday night's final round. A second preliminary round is scheduled for tonight, with the 2026 winner crowned Saturday evening at Sloppy Joe's. 

For many competitors, the annual contest is as much a reunion as it is a competition. It's an annual pilgrimage to Key West, where they can reconnect with friends who understand the walk, the crowd and the dedication required to dress like Ernest Hemingway in July. 

The contest is the highlight of Hemingway Days, an annual Key West celebration of the author's literary legacy, sporting pursuits and island years. The 2026 festival continues through Sunday with events including the lighthearted "Running" of the Bulls outside Sloppy Joe's, a dockside fish-off, a street fair and a belated birthday bash marking the 127th anniversary of Hemingway's July 21 birth. 

Beyond the fun, the look-alikes also carry a cause beyond the stage. The Hemingway Look-Alike Society, formed by past winners and contestants, raises money for scholarships for College of the Florida Keys students and has awarded more than $350,000 since its inception. 

To learn more, visit KeyWestLookAlikes.com. 

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Photo Captions:  

HemingwayRoundOne_01.jpg  

Chris Dutton of Tampa, Fla., strikes a pose on stage at Sloppy Joe’s Bar in Key West, Fla., after announcing to the judges and audience of the 45^th annual Hemingway Look-Alike Contest his goal of becoming the youngest winning “Papa” in the competition’s history. The first round of this contest took place on Thursday, July 23, 2026, with contestants vying for the title as part of the six-day Hemingway Days festival celebrating Nobel Prize-winning author Ernest Hemingway and his enduring connection to the island. (Carol Tedesco/Florida Keys News Bureau) 

HemingwayRoundOne_02.jpg  

Peter McHugh of Tucson, Arizona, makes his case to the judges during the opening round of the 45^th annual “Papa” Hemingway Look-Alike Contest, Thursday, July 23, 2026, at Sloppy Joe’s Bar in Key West, Fla. The contest is a signature event of the six-day Hemingway Days festival that has attracted contestants and fans from around the world since 1981 to celebrate Nobel Prize-winning author Ernest Hemingway’s legacy. Events continue through Sunday, July 26, 2026. (Carol Tedesco/Florida Keys News Bureau)

HemingwayRoundOne_03.jpg  

Don Weinstein of Ocoee, Florida, channels Nobel Prize-winning author Ernest Hemingway’s safari persona during the opening round of the 45^th annual “Papa” Hemingway Look-Alike Contest, Thursday, July 23, 2026, at Sloppy Joe’s Bar in Key West, Fla. The contest is a signature event of the six-day Hemingway Days festival that has attracted contestants and fans from around the world since 1981 to celebrate Hemingway, whose Key West home remains one of the island's best-known historic landmarks. The festival continues through Sunday, July 26, 2026. (Carol Tedesco/Florida Keys News Bureau) 

HemingwayRoundOne_04.jpg  

Twelve finalists from a field of more than sixty competitors, enjoy a moment of triumph at the conclusion of the opening round of the 45^th annual “Papa” Hemingway Look-Alike Contest, Thursday, July 23, 2026, at Sloppy Joe’s Bar in Key West, Fla. The competition, a signature event of a six-day Hemingway Days festival, continues with a second round on Friday, July 24, and with the final round on July 25. Events continue through Sunday, July 26, 2026. (Carol Tedesco/Florida Keys News Bureau)