The Old Man and the Keys – 6 Ways to Experience Key West Hemingway Style

Ernest Hemingway ended up in Key West like many others — by accident. He came for a day and ended up staying for a decade. That was close to a century ago, and the town has yet to recover from his presence.

Papa’s spirit permeates the island. His former home, complete with a gaggle of six-toed cats, remains one of the most popular tourist attractions. Each July more than 100 white-bearded men wearing sweaters and safari khaki shorts storm the streets for the largest look-alike contest in the world. Thanks to him, Key West endures as a haven for writers and other artists.

It is easy to simultaneously admire and curse the man. He was an imposing character, a larger-than-life egoist heavy of drink and quick of wit. He slayed hundreds of animals, hunted Nazi U-boats with hand grenades, survived two plane crashes, gunned down sharks with a Thompson submachine gun to save his tuna catch (it didn’t work), won Pulitzer and Nobel prizes, inspired generations of creative talent, and once reassured F. Scott Fitzgerald that his penis was of a standard size.

To this end, a truly honest Hemingway-style experience in Key West could entail instigating a number of bar brawls, stealing the urinal from your favorite drinking establishment, getting a divorce or two and spending your last penny. Ideally, however, it will not need to include any of those, because there are more imaginative ways to revel in Hemingway’s Keys, most of which do not involve jail time and liver damage.

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#1 – Fish the Northwest Passage. Locals call the remains of the Northwest Passage lighthouse off Key West the “Hemingway Stilts” after the avid angler who cherished this fishing hole. It might be a stretch to break his world record of landing seven marlin in a day, but you’re bound to at least get some yellowtail and grouper for dinner.

#2 – Indulge in Life’s Pleasures. Hemingway savored food, drink and friends, and often during his travels sought out the finest meals and drinking establishments. Grab some companions for a delectable breakfast at Blue Heaven, the former home of his boxing ring, then mosey over to Sloppy Joe’s or Capt. Tony’s Saloon, both buildings in which he downed many a libation. For extra authenticity and hangover eschew, avoid his nemesis, blended and sweetened concoctions.

#3 – Get marooned at Dry Tortugas. It was 1930 when a storm blew in, stranding Papa and his fishing crew for two weeks on Garden Key, 70 miles west of Key West. They hid in a shed at abandoned Fort Jefferson, braved the wind to catch what fish they could, and mostly survived off of the 24 cans of spaghetti and 12 cans of beans they happened to bring along. It’s not recommended to brave the Tortugas in a storm, but it is an healthy adventure to camp there for a few nights. Plus, SpaghettiOs do taste a lot better when eaten on a beach under starlight.

#4 – Create a Masterpiece. Dream and communicate something into the world that you think is worthwhile. Write a poem. Tell a story to children. Start up a conversation with strangers. That is something particularly easy to do in this friendly town. Or, just read one of Hemingway’s creations inspired by his time in Key West and Cuba: To Have and Have Not, The Old Man and the Sea, and Islands in the Stream. Start your inspiration with a stop at his writing room, preserved in the Hemingway House museum in Key West.

#5 – Try On Your Own Legendary Style. “Whatever your style, find it and flaunt it,” is not a quote by Hemingway, but it should be. Key West is known for its come-as-you-are acceptance of all people. So what better place to find your defining style and the confidence that comes with it? Just as Hemingway is forever known for his sweaters and Jimmy Buffett for his lack of shoes, there’s a new set of duds waiting for you somewhere in town, poised to create the next legendary look.

#6 – Experience One Good, True Adventure. Hemingway traveled widely, experienced much, learned courage and lived life for each savory moment. There’s no better way to exploit Key West Hemingway style than adventuring outside of your comfort zone. Learn to scuba, ride a parasail or finally get up the nerve to ask out that lovely gal or or handsome guy you’ve been eyeing. It might be intimidating, but ultimately no one regrets a grand adventure.

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About the Author

Karuna Eberl writes from the Florida Keys, on matters of travel, nature, history and kindness. She co-authored Quixotic Key West & the Lower Keys Travel Guide (Quixotic Travel Guides), which recently won the Best Travel Book award from the American Book Festival.