Skip to Content

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 Hemingway, Key West endures as a haven for writers and other artists.

key west hemmingway bulls 1024 1 6 ways to experience Key West, Hemingway style
Hemingway in Key West: The author is celebrated on his birthday every July in Key West. (Florida Keys News Bureau.)

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 Key West, most of which do not involve jail time and liver damage.

Hemingway Days, July 18-21, 2024

Key events are Sloppy Joe’s popular Hemingway Look-A-Like Contest and Running of the BullsOther festival events include museum exhibits of Hemingway memorabilia at the Customs House Museum, the Key West Art & Historical Society’s symposium featuring scholars and writers, the annual “Papa’s Poems” reading by the Key West Poetry Guild, the Hemingway 5k Sunset Run and Paddle , the Key West Marlin Tournament and street fair.

Experience Key West like Hemingway

Fish the Northwest Passage

Hemingway Key West: swordfish
For Hemingway, Key West was a favorite fishing spot (Photo/Andy Newman/Florida Keys News Bureau)

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.

TripAdvisor: Key West fishing charters

Indulge in Life’s Pleasures

Hemingway in Key West: The original Sloppy Joe's is now Capt. Tony's Saloon.
Hemingway in Key West: The original Sloppy Joe’s is now Capt. Tony’s Saloon. (Photo/Sam Howzit/Creative Commons)

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.

Related story: Most Beloved ‘Locals’ Bars in Key West

Get marooned in the Dry Tortugas

key west Dry Tortugas beach e1352999258111 6 ways to experience Key West, Hemingway style
Hemingway, Key West: He was famously marooned on a beach at the Dry Tortugas National Park: Campsites are steps away. (Photo/Bonnie Gross)

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 a healthy adventure to camp there for a few nights. Plus, SpaghettiOs do taste a lot better when eaten on a beach under starlight.

Related story:  Camping at the Dry Tortugas National Park

Create a Masterpiece

Hemingway in Key West: Ernest Hemingway's writing room.
Hemingway in Key West: Ernest Hemingway’s writing room. (Photo/Rob O’Neal/Florida Keys News Bureau)

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 Home museum in Key West.

Here’s a link to the Hemingway Home and Museum.

Try On Your Own Legendary Style

Hemingway: Key West isn't known for its sweaters weather, but Ernest Hemingway's is famous.
Hemingway: Key West isn’t known for its sweater weather, but Ernest Hemingway’s is famous for this look.

“Whatever your style, find it and flaunt it,” is not a quote by Hemingway, but it could be about him. 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.

Discover your style at these Key West specialty shops on Tripadvisor

Experience One Good, True Adventure

Kite-boarding at Curry Hammock State Park near Marathon
If Hemingway were alive today, no doubt he would try kite-boarding. (Photo/Nick Ziegler)

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 handsome guy you’ve been eyeing. It might be intimidating, but ultimately no one regrets a grand adventure.

Here’s a link to Key West adventures on Tripadvisor

More related stories

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Dave Mullineaux

Thursday 3rd of June 2021

we were there in Feb. We will go back. Loved it


Friday 12th of June 2020

Thanks for this great article!! I've always been one of those people who "simultaneously admire and curse the man." In someways I want to be like him in the sense of living life to the fullest and having adventures, and in others ways I want to be nothing like him--such as my relationship with my family. Also, thanks for the pic of the look-alike contest. I've always heard about it, but never actually seen what it looks like!

This site uses Akismet to reduce spam. Learn how your comment data is processed.