The Gates Guide to Hemingway Days in Key West 2022

Ernest “Papa” Hemingway wasn’t just an American icon, he was a Key West icon. The famed literary giant spent much of his time on the island, living in the 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 19 - 24, 2022 it’s an especially fun way 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 2022:

Meet the “Papas” at Sloppy Joe’s, July 20

Kick off the annual Hemingway Days surrounded by a bunch of Papa look-alikes. Sloppy Joe’s is hosting a gathering at 5:30 p.m. for a chance to get to know this year’s look-alikes and meet 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 23rd outside Sloppy Joe’s on Greene Street.

The Key West Marlin Tournament at Stock Island Marina, July 20 - 23

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 40th anniversary tournament consists of three days of fishing (with the first day coinciding with Hemingway’s 123rd birthday), 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’s 123rd Birthday Celebration, July 21

Commemorate the 123rd anniversary of Hemingway's July 21 birth on-stage at Sloppy Joe’s with a very special ‘Papa’ birthday cake.

Hemingway Look-Alike Society Contest at Sloppy Joe’s, July 21 - 23

One of the most eye-catching events of Hemingway Days, the Hemingway Look-Alike Contest, is hosted by none-other than Sloppy Joe’s - Papa’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 41st annual event will be held on-stage Saturday, July 23 at 6:30 p.m.

Hemingway Trivia Hunt, July 21 - 25

Test your knowledge of the author during the Hemingway Trivia Hunt. The hunt takes you to some of Ernest’s local haunts and sites around town. Get your game card online, participate on any day of the event, and submit your answers the same night to win entries to next year’s Hemingway 5K and Paddleboard Race, the Key West Half Marathon, and more.

Hemingway Days Caribbean Street Fair on Duval Street, July 23

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.

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Hemingway 505 Bike Tour, July 23

The 11th annual Hemingway 505 Bike Tour is back with a 10 a.m. start time at Sombrero Beach in Marathon. Ride the 50 miles south to Key West before running the Hemingway 5K Sunset Run (more on that below). Stops include Kiki's Sandbar on Little Torch Key, Baby’s Coffee, and Key West Waterfront Park. Your admission fee includes hydration stations along the route.

Hemingway 5K Sunset Run/Walk and Paddleboard Race, July 23

Test your skills and celebrate Hemingway’s sporting lifestyle during the 33rd annual Hemingway 5K Sunset Run/Walk and Paddleboard Race. Meet at Sea at 720 Caroline Street at 11 a.m. for a pre-race power brunch. The paddleboard race begins at 5:30 p.m. from Southernmost Beach, and the 5K begins at 7:30 p.m. from Southernmost Point. Ease your muscles with a post-race recovery yoga session at The Perry Hotel & Marina Key West the following morning at 8:45 a.m. 

Running of the Bulls Key West on Greene Street, July 23

This is one of our favorites. Every year, Hemingway look-alikes come to Key West for the “Running of the Bulls” outside Sloppy Joe’s on Greene Street. Fortunately, this isn’t an ordinary running of the bulls, but a leisurely stroll with the bulls (in true Key West fashion). 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 and join in on the fun. The event starts at 1 p.m.

Hemingway Home and Museum, Open Daily

Go inside Hemingway’s tranquil studio, home, and gardens where the Pulitzer Prize-winning author penned some of his greatest novels and stories. No doubt a visit to 907 Whitehead Street during Hemingway Days will be extra special. You'll also see living descendants of the 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 following the narrative of Hemingway’s Pulitzer Prize-winning novel by internationally-renowned marine wildlife artist and conservationist, Guy Harvey. 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.

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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 residents.