Key West Festival Honors Hemingway's Writing and Colorful Lifestyle

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Jun 12, 2026, 08:36 ET

KEY WEST, Fla., June 12, 2026 /PRNewswire/ -- In his novel "To Have and Have Not," Ernest Hemingway painted a compelling portrait of Depression-era Key West, his home in the 1930s. The 2026 Hemingway Look-Alike Contest and festival, scheduled Tuesday through Sunday, July 21-26, celebrates his influence — highlighted by the famed Look-Alike Contest at Sloppy Joe's Bar, 201 Duval St., and creative events that honor his writing talent.

Ernest Hemingway, who lived in Key West, Fla., during the 1930s, stands at the wheel of his fishing boat Pilar. The legendary writer's talent and exuberant lifestyle are celebrated during the Hemingway Look-Alike Contest and festival, set for July 21-26 in the island city. (Photo courtesy of Ida Woodward Barron Collection/Florida Keys History Center)

Attendees at the Hemingway Look-Alike Contest and festival, set for July 21-26 in Key West, Fla., can view rare memorabilia from Ernest Hemingway's life during an exhibit at the Key West Museum of Art and History at the Custom House. Two "Hemingway Collection" museum days are among the events honoring the legendary writer's talent and exuberant lifestyle. (Photo by Peter Maczek/Courtesy of Key West Art & Historical Society)

The festival's July 21 opening night, the 127th anniversary of the legendary writer's birth, begins with the announcement and reading of the Lorian Hemingway Short Story Competition's winning entry. The literary challenge is directed by Ernest's author granddaughter Lorian and awards $2,500 annually to deserving writers.

Scheduled for 6 p.m. at Key West's Williams Hall, 729 Fleming St., the reading is followed by a screening of "The Beard Also Rises." The short film by Cassidy Rast and Odin Wadleigh celebrates the world-renowned annual Hemingway Look-Alike Contest and its winners and entrants. Also planned is a "trailer" preview of the duo's "Beards Go to Cuba," showcasing the Look-Alikes' philanthropic activities in support of the Cuban people.

At 8:15 p.m. that night, Williams Hall will show "The Old Man and the Sea," the classic 1958 film based on Hemingway's masterful novella, "The Old Man and the Sea." Spencer Tracy stars as Santiago, a Cuban fisherman who wages an epic battle with a giant marlin.

Cultural events continue Thursday, July 23, with an exploration of Hemingway's love of Florida Keys angling and his lesser-known fisheries conservation activities. "Following the Fish: Hemingway in Key West" is presented by Cori Convertito, Ph.D., curator of the Key West Art & Historical Society. Part of her popular "Happy Hour with the Historian" series, it's set for 5-6 p.m. at Comedy Key West, 218 Whitehead St.

A salute to Ernest's storytelling skill is planned for 1-4 p.m. Sunday, July 26, in an establishment that's home to the award -winning Papa's Pilar Rum. The "Papa's Tales" Storytelling Competition will take place at the Hemingway Distillery's Hemingway Social Club, 201 Simonton St. Entrants in two categories must spin a spoken-word tale of three minutes or less, with judges evaluating them on style, delivery and originality. Entry is free and the grand prize includes the Barrel Head Trophy.

The cultural schedule is bookended Tuesday and Sunday, July 21 and 26, by "Hemingway Collection" museum days at the Key West Museum of Art and History at the Custom House, 281 Front St. Attendees can view rare artifacts and memorabilia from the author's life, a full-size bronze of him, and 59 original drawings by famed marine wildlife artist Guy Harvey illustrating "The Old Man and the Sea." Admission is free to those who mention the Hemingway festivities upon arrival.

The Hemingway Look-Alike Contest and festival is presented in part by the Monroe County Tourist Development Council. For details and a full event schedule, visit www.keywestlookalikes.com.

Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: [email protected]

SOURCE Sloppy Joe's Bar