Hemingway Days: A Celebration Of The Legendary Author’s Legacy In Key West

Starting on Tuesday, thousands of Ernest Hemingway fans will descend on Key West to celebrate the legendary author’s life, legacy and connection to the island city

“It’s the best place I’ve ever been anytime, anywhere, flowers, tamarind trees, guava trees, coconut palms…”

For the well-traveled Hemingway, there was no place in the world like Key West. He fell in love with the island city in 1928 during what was supposed to be a short delay that turned into an extended stay. He found Key West to be a place where he could live an adventurous life while still having the seclusion to write. 

That’s why, in one form or another, the festivities of the 39th annual Hemingway Days are an ode to him, his lifestyle or his works. 

On day one of the celebration, the Key West Art & Historical Society is hosting a 2-hour symposium. Attendees will learn about Hemingway’s first attempt to fictionalize Key West, what the area was like during his time there and 99-year-old letters of his. Registration is required and there’s a $5 entry fee for non-Key West Art & Historical Society members.

Literary fans can enjoy “Voices, Places, Inspirations” on day two. The Key West Poetry Guild kicks off the event with “Papa’s Poems” before a series of presentations and readings. This experience takes place at Old City Hall and admission is free. 

Also on Wednesday is “Meet the Papas,” where the contestants of the Sloppy Joe’s Hemingway Look-Alike Contest meet up at the bar a day before the first preliminary round.  

Thursday is the start of the Key West Marlin Tournament. Anglers take to the sea starting at 8:30 in the morning before returning for weigh-in between 4 p.m. and 6 p.m. This is followed up by an island-style pig roast.

Back at Sloppy Joe’s Bar, the winners of the Hemingway Look Alike Society Scholarship Program are announced. About a half hour after the presentation, the first round of the look-alike contest takes place. Entry for the look-alike contest is $35.

The fishing tournament continues on its same schedule on Friday.  

At 11:15 in the morning, Richard Abella’s “Hemingway: Between Key West and Cuba” will be screened at the Tropic Cinema. The documentary takes a look at how Hemingway was influenced by the culture and people of the two islands. 

In the afternoon, Hemingway look-alikes will compete in the dockside catch-and-release “Papa Look-Alike Fish-Off.” The “Papas” will then head to Sloppy Joe’s for the second preliminary round.

Saturday offers the most events, starting off with the third and final day of the Key West Marlin Tournament. Anglers will head back to the docks for weigh-in between 3 and 5 p.m. before the awards banquet, silent auction and dinner at 6:30 p.m.

The Caribbean Street Fair presented by Literacy Volunteers of America–Monroe County takes place from 10 a.m. to 10 p.m. Fair-goers can browse blocks of booths displaying original art, jewelry and clothing.

The looniest experience is the “Running of the Bulls” hosted by Sloppy Joe’s. Hemingway look-like winners and contestants dress as if they are in Pamplona, Spain for the world-renowned event. Pushing wooden bulls on wheels, the wannabe Hemingways run wild on the streets of Key West.

The Hemingway 5k Sunset Run/Walk starts at 3 p.m. and the Paddleboard Race begins at 5:30 p.m. The run/walk is $50 to participate, the paddleboard race is $45 or $90 for both. The post-race awards are handed out during a party at the Southernmost Beach Cafe.

But the pièce de résistance of Saturday is the final round of the Hemingway Look-Alike Contest at 6:30 p.m. Former winners like Michael Groover, husband of cooking show host Paula Deen, will select the latest member to join their brotherhood.

“I call it persistence,” Groover told the Keys Voices blog. “I think everybody here really has to pay their dues, and I did.”

Grover, who won in 2018, added that winning was just as important as the friendships he forged. 

“I feel a kinship, because I love fishing and hunting,” he explained. “I think it’s incredible that I won any day, but it means a lot that it’s on his birthday. I’m just happy to be a part of this group.”

The Hemingway Days festivities wrap up on Sunday with “Bloody Marys with Papa” and an arm-wrestling contest at Sloppy Joe’s.