For nearly a century, Key West has been a haven and an inspiration for some of the United States’ most influential writers. But none was more influential than Ernest Hemingway, who lived and wrote on the island for most of the 1930s.

Hemingway with fish

Ernest Hemingway (right) was a passionate angler during his Key West years. (Photo courtesy of the Key West Art & Historical Society)

Fans of adventurous living and masterful writing can celebrate Hemingway’s legacy Tuesday through Sunday, July 19-24. Each year, the Hemingway Days festival salutes the author’s vigorous Key West lifestyle, sporting pursuits and extraordinary creative talent.

As many as 150 burly, bearded contestants are expected to compete in the annual Hemingway® Look-Alike Contest at Sloppy Joe’s Bar. So expect to see dozens of “Ernests” hanging out at the historic saloon where Hemingway often enjoyed cocktails with cohorts — and whose original owner was his good friend and fishing companion, Joe Russell.

The contest’s preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 21 and 22, with finalists facing off at 6:30 p.m. Saturday, July 23.

Held in conjunction with the festival is the Lorian Hemingway Short Story Competition coordinated by Ernest’s granddaughter, author Lorian Hemingway. Each year the contest awards $2,500 to emerging writers, with the winners to be announced — and the top story given its first public reading — at 6 p.m. Wednesday, July 20, at Key West’s Monroe County Public Library.

The announcement will be paired with another can’t-miss event for fans of fine writing: the acclaimed Key West Poetry Guild’s annual showcase of Hemingway’s little-known poetry and their own work.

Ernest Hemingway bronze Key West

This life-size bronze sculpture of Ernest Hemingway can be seen during the “Hemingway Collection” museum days at Key West’s Custom House Museum. (Photo by Rob O’Neal, Florida Keys News Bureau)

The festival also features two “museum days” where visitors can view a unique Hemingway exhibit at Key West’s Custom House Museum — plus 59 original pen-and-ink drawings by marine wildlife artist Guy Harvey that provide a visual narrative to the author’s classic novel, “The Old Man and the Sea.”

Speaking of the sea, anglers can share “Papa’s” passion for deep-sea fishing during the Perry Hotel & Marina Key West Marlin Tournament, set for Wednesday through Saturday, July 20-23. Participants can pursue marlin and spearfish, sailfish, tuna, dolphin fish and wahoo while competing for a whopping $50,000 in guaranteed cash prizes.

Among other festival attractions are Sloppy Joe’s offbeat “Running of the Bulls” (spoiler alert: it’s more of a stroll than a run, and it features scores of Hemingways and several manmade bulls), a commemoration (with cake!) on the 123rd anniversary of Hemingway’s July 21 birth, a street fair along the Duval Street blocks he once walked, and a 5k run and paddleboard race that recall his sporting lifestyle.

Ernest Hemingway lived in Key West from 1931 until late 1939, penning literary classics including “For Whom the Bell Tolls” and “To Have and Have Not” — the latter set primarily in the island city he called home. So it’s no surprise that several Key West sites are associated with his presence.

The best-known is the Spanish colonial villa at 907 Whitehead St. where he lived with his second wife Pauline. Now a registered National Historic Landmark, it’s open to the public as the Ernest Hemingway Home & Museum. Its notable features include the island’s first swimming pool and a colony of cats — many of them six-toed — that are descended, so the story goes, from a sea captain’s feline given to the author.

Hemingway look-alike winner Key West

Zach Taylor, center, surrounded by past winners of the Hemingway Look-Alike Contest, beams as he hoists a bust of Ernest Hemingway after winning the 2021 contest at Sloppy Joe’s Bar in Key West. (Photo by Andy Newman, Florida Keys News Bureau)

Hemingway wrote many of his best-known works in the second-story studio that adjoins the Whitehead Street house. The home that nurtured the legendary writer’s talent is well worth a visit, and guided tours are offered daily.

Many Hemingway fans also seek out the onetime Key West Arena, located at the corner of Thomas and Petronia streets in Bahama Village, the site of open-air neighborhood boxing matches that Hemingway sometimes refereed. Today the popular Blue Heaven Restaurant, where the food is “Caribbean casual” and the Key lime pie is world-renowned, occupies the former arena site.

Ernest Hemingway might have left Key West in late 1939, but his legacy lingers on. Just ask the Look-Alikes who flock to Sloppy Joe’s, the writers who followed him seeking creative inspiration, or anyone who has ever walked the halls and grounds of his island home.