Ernest Hemingway’s larger-than-life legacy is woven into the historic fabric of Key West. The Pulitzer Prize winning author made the island his home and playground throughout the 1930s--the most productive decade of his life. Pull back the curtain of time, and you’ll find his “St. Tropez of the poor” during July’s Hemingway Days Festival when the Southernmost City is flooded with hundreds of doppelgangers all vying to win the look-alike contest at Sloppy Joe’s Bar.
Greg Fawcett, center front, is crowned the winner of the 2012 "Papa" Hemingway Look-Alike Contest. — Photo courtesy of Photo by Andy Newman/Florida Keys News BureauStart your weekend getaway by picking up some weekend reading at the lone remaining bookstore in Key West, Key West Island Books, on Fleming Street. Peruse their vast collection of works by and about Hemingway. To Have and Have Not, his hard-scrabble novel about Key West during the Depression is a good choice. Hemingway’s Key West, by Stuart B. McIver chronicles the literary icon’s exploits and lists a walking tour of his old haunts.
Then head to the funky Blue Heaven Restaurant in Bahama Village to feast on Caribbean flavors. Pork tenderloin with mango chutney pairs perfectly with their infamous Key lime pie and its mile-high meringue. Imagine the space as the former open-air Key West Arena, where Hemingway showed off his notorious machismo, sparring with local fighters.
Sunset view from the top of Crowne Plaza La Concha Hotel. — Photo courtesy of Photo by Claudia MillerStay at the Crowne Plaza La Concha Hotel on Duval Street where Hemingway was a guest several times before buying a home. At seven stories, this 1926 National Historic Landmark was–and still is–the tallest building in Key West. The rooftop deck offers sweeping 365-degree views of the Atlantic and the famous sunset on the Gulf of Mexico.
On Saturday, check out touchstones from the author’s life at the Custom House Museum at the end of Duval Street. On display are items like his bloody WWI uniform, well-worn boxing gloves, Underwood Standard typewriter and photos of the writer fishing on his beloved boat Pilar.
Stop at Captain Tony’s Saloon on Greene Street, a former speakeasy and the original location of Sloppy Joe’s until 1937. Hemingway was a fixture here, knocking back Teacher’s scotch and soda with owner Josie Russell. A rumrunner and charter captain, Russell often served as his boat pilot and frequent fishing companion. Hemingway met his third wife, writer Martha Gellhorn, here; their romance was dramatized in the HBO film Hemingway and Gellhorn last year.
Ernest Hemingway look-alikes push fake bulls on Duval Street during the "Running of the Bulls." — Photo courtesy of Photo by Andy Newman/Florida Keys News BureauIn the early afternoon, watch over 50 bearded men dressed in white with red berets swarm onto Duval Street pushing fake bulls during the Running of the Bulls. The lively event is a spoof of its namesake challenge in Pamplona, Spain, which was featured in The Sun Also Rises. (Insider fact: this event was a failure the first time in 1981. The look-alikes actually wore bull costumes, but almost passed out in 92-degree temps.) Post-run, the “Papas” celebrate Hemingway’s birthday with a cake and additional antics–i.e. don’t expect them to use forks.
Supporters of Pat Lanier cheer him on during the Look-Alike Contest at Sloppy Joe's. — Photo courtesy of Photo by Andy Newman/Florida Keys News BureauFind a spot early at Sloppy Joe’s for the final round of the “Papa” Hemingway Look-Alike Contest. The place gets packed with fans chanting and waving signs for their favorite contestant. Spectators spill out into the streets. To beat the heat, try a refreshing Papa Dobles, Hemingway’s fave cocktail, made with Bacardi, Maraschino Liqueur, lime and grapefruit juices. Judged by the past winners, the portly bearded men in khaki sportsman’s garb play to the crowd with a boisterous speech, song or poem. The victor is bestowed a medal to great fanfare. Celeb alert: TV chef Paula Deen cheered on her husband at the finals last year.
Six-toed cat takes a nap at the Hemingway House. — Photo courtesy of Photo by Claudia MillerOn Sunday, tour the Hemingway Home & Museum, a Spanish colonial villa on Whitehead Street for a glimpse into the writer’s private life. Look for the penny encased in glass by the pool. Hemingway tossed it on the ground in protest of the $20,000 his wife, Pauline, spent on the swimming pool–the first in Key West. She preserved the penny there after he exclaimed she might as well take his last cent. Over 40 six-toed cats lounge under tropical fruit trees and curl up on antique furniture. They sip water at the urinal-turned-fountain from the original Sloppy Joe’s. Legend says Hemingway’s first six-toed cat was a gift from a ship’s captain.
Climb the stairs of the carriage house to the second-story writing studio lined with hunting trophies where he completed many of his best works, including Death in the Afternoon, For Whom the Bell Tolls, The Green Hills of Africa and The Snows of Kilimanjaro. Hemingway established Key West as a literary haven, and many notable writers followed in his footsteps like Tennessee Williams, Robert Frost, Ralph Ellison and Annie Dillard. Perhaps seeing the island through Hemingway’s eyes will inspire the writer in you?
