Ernest “Papa” Hemingway wasn’t just an American icon, he was a Key West icon. The famed literary giant spent years on the island, living in his gorgeous Spanish Colonial on Whitehead Street. There he penned some of his most successful novels like A Farewell to Arms and Death in the Afternoon.

Every July it’s Key West tradition to celebrate Hemingway, commemorating his birthday with the week-long festival Hemingway Days. Hemingway Days is a culmination of all things “Papa”, with cultural events, fishing tournaments, look-alike contests, and more. If you’re visiting Key West from July 18 - 23, 2023 it’s an especially fun time to brush up on your Hemingway knowledge and see the island at the same time.

Here are the events you can’t miss at Hemingway Days Key West 2023:

Meet the “Papas” at Sloppy Joe’s, July 19

Kick off the annual Hemingway Days surrounded by a bunch of Papa look-alikes. Sloppy Joe’s is hosting the Meet the “Papas” gathering at 5 p.m. Meet this year’s look-alikes and previous winners of the iconic contest taking place later in the week. You’ll get another chance for a photo opportunity at noon on the 22nd outside Sloppy Joe’s on Greene Street.

Key West Marlin Tournament, July 19 - 22

Considering that Hemingway was an avid deep-sea angler, it only makes sense that the annual Key West Marlin Tournament is held during Hemingway Days. The 41st anniversary tournament consists of three days of fishing, nightly festivities, cocktail parties, and dinners - with evening marlin weigh-ins at the Stock Island Marina Village. Winners take home $50,000 in cash prizes.

Hemingway Look-Alike Society Contest at Sloppy Joe’s, July 20 - 22

One of the most eye-catching events of Hemingway Days, the Hemingway Look-Alike Contest, is hosted by none-other than Sloppy Joe’s - Hemingway’s go-to bar during his days in Key West. Hundreds (yes, hundreds) of Hemingway look-alikes come from all over the world to compete. Frankly, it’s quite surprising to see just how many Hemingway doppelgangers exist. Come see for yourself. The final round of the 42nd annual event will be held on-stage Sat., July 22 at 6:30 p.m.

Hemingway Days Caribbean Street Fair on Duval Street, July 22

The annual Hemingway Days Caribbean Street Fair will be held on Duval Street from 10 a.m. to 10 p.m. The famed avenue will be closed to vehicular traffic and transformed into an open-air marketplace spanning several blocks with island food, drinks, and original arts and crafts booths. The street fair attracts over 15,000 locals and visitors annually.

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Hemingway 505 Bike Tour, July 22

The 12th annual Hemingway 505 Bike Tour is anticipated to take place on July 22 and begin at 10 a.m. from Sombrero Beach in Marathon (this year’s event is still being finalized). Ride the 50 miles south to Key West Waterfront Park before running the Hemingway 5K Sunset Run (more on that below). Stops along the route to mingle with fellow riders have included Kiki's Sandbar on Little Torch Key and Baby’s Coffee. Your admission fee includes hydration stations along the route. Register ahead.

Running of the Bulls Key West on Greene Street, July 22

This is one of our favorites. Every year, Hemingway look-alikes come to Key West to participate in the “Running of the Bulls” outside Sloppy Joe’s on Greene Street. Fortunately, this isn’t an ordinary run of the bulls, but a leisurely stroll with the bulls. Think hundreds of Hemingways, all dressed in their Pamplona red and white, steering manmade bulls on wheels down Greene. It’s definitely a sight to see. Grab a daiquiri (Hemingway’s favorite) and join in the fun. The event starts at 1 p.m.

Hemingway 5K Sunset Run/Walk and Paddleboard Race, July 22

Test your skills and celebrate Hemingway’s sporting lifestyle during the 34th annual Hemingway 5K Sunset Run/Walk and Paddleboard Race. The paddleboard race begins at 5:30 p.m. from Higgs Beach, followed by the 5K at 7:30 p.m. from Southernmost Point. Register ahead.

Hemingway Rum Stroll, July 23

The inaugural Hemingway Rum Stroll is slated for 12 - 3 p.m., with additional details still in the works. The stroll will be presented by the organizers of the 5K and paddleboard race, so stay tuned to their website for more information on what is sure to be a new Hemingway Days Key West favorite.

Hemingway Home and Museum, Open Daily

Go inside the Hemingway Home & Museum, studio, and gardens where the Pulitzer Prize-winning author penned some of his greatest novels and stories. No doubt a visit to 907 Whitehead St. during Hemingway Days Key West 2023 will be extra special. You'll also see living descendants of Hemingway’s legendary original six-toed cats! Now a registered National Historic Landmark, the museum is open daily from 9 - 5 p.m. and admission includes a 20 - 30 minute guided tour.

‘Depicting Hemingway: Guy Harvey Sketches The Old Man and the Sea’ Museum Exhibition at the Custom House Museum, Open Daily

The Custom House Museum’s permanent exhibition ‘Depicting Hemingway: Guy Harvey Sketches The Old Man and the Sea’ is on-view throughout Hemingway Days. The exhibition features 59 original pen-and-ink drawings by internationally-renowned marine wildlife artist and conservationist, Guy Harvey, and follows the narrative of Hemingway’s Pulitzer Prize-winning novel. You’ll also see artifacts like the life-sized bronze ‘Ernest Hemingway in Key West’ statue by sculptor Terry Jones, a 1930s-era ‘Hemingway and Friends’ painting depicting the author at Sloppy Joe’s, and a pair of Hemingway’s boxing gloves. The museum is open daily from 10 - 5 p.m.

If you’re thinking about a visit to Key West, don’t delay! It’s always summer in the Conch Republic. The Gates Hotel is a Condé Nast award-winning hotel located in New Town and offers shuttle service close to all the Hemingway festivities in Old Town. Exciting onsite amenities - like a food truck, cigar lounge, and a spectacular swimming pool - puts The Gates in its own special category. Check out our special offers online, including perks just for Florida and Georgia residents.