Tom Grizzard, 69, of Leesburg bested 141 other contenders in the competition at Sloppy Joe's Bar, Hemingway's favourite watering hole when he lived in Key West throughout the 1930s.
"I relate to his love of the sea and love of people," said Grizzard. The eight-time competitor wore a cream-coloured turtleneck sweater suggesting Hemingway's garb in an iconic 1957 photo portrait by Yousuf Karsh.
Look-alike contenders in sportsman's attire paraded across the stage at Sloppy Joe's during preliminary rounds before a judging panel of former winners.
Twenty-five prospective "Papas" made it to the finals.
Other Hemingway Days events included the Drambuie Key West Marlin Tournament, writers' readings and a short story competition directed by author and Hemingway granddaughter Lorian Hemingway.
Ernest Hemingway's grandson Edward Hemingway, a writer and illustrator who showcased his new children's book at the festival, said he thought Hemingway Days would appeal to his late grandfather.
"I imagine my grandfather would get a kick out of the festival," he said. "The spirit of his life is here in Key West."
During his 10-year residence on the island, Ernest Hemingway penned literary classics including For Whom the Bell Tolls, The Snows of Kilimanjaro and To Have and Have Not.
Hemingway would have turned 109 on Monday.
