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Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

The Gates Guide to Hemingway Days in Key West

The Gates Guide to Hemingway Days in Key West

June 30th, 2021 | Key West Events & Festivals

Ernest 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 20 - 25, 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 2021:

The Key West Marlin Tournament @ Stock Island Marina, July 21 - 24

Considering that Papa Hemingway was an avid deep-sea angler, it only makes sense that the annual Key West Marlin Tournament is held during Hemingway Days. The tournament consists of three days of fishing (beginning on the 122nd anniversary of Ernest Hemingway’s birth), with evening weigh-ins at the Stock Island Marina Village. Winners take home $50,000 in cash prizes.

Key West Art & Historical Society’s Hemingway Days events, July 22 - 23

Hemingway history buffs and culture junkies: these are events you don’t want to miss. The KWAHS provides expert insight into Hemingway’s passions with the virtual Key West to Bimini: Hemingway’s Big-Game Fishing Evolution talk on July 22. Join English Professor and Hemingway scholar Dr. Ashley Oliphant for an engaging walk through Hemingway’s big-game fishing education beginning with his move to Key West in 1928. The following night, the mother/daughter research team of Dr. Ashley Oliphant and Beth Yarbrough will lead a hilarious Hemingway Days Twilight Walking Tour of the Old Town sites where Hemingway lived, wrote, and drank. The July 23 event begins at 6 p.m. and concludes with a sunset happy hour on the veranda of the Custom House with Hemingway-inspired rum beverages. In addition, keep a lookout for the Custom House’s two Hemingway “museum days” which are scheduled to showcase a rare collection of the author’s documents, memorabilia, and personal belongings.


Hemingway Look-Alike Contest @ Sloppy Joe’s, July 22 - 24

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 Papa 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 will be held on stage on Saturday, July 24 at 6:30 p.m.

Hemingway Trivia Hunt, July 22 - 26

New to the lineup this year, the Hemingway Trivia Hunt lets you test your knowledge of the author. The hunt takes you to some of Ernest’s local haunts and sites around town that honor him. Participate on any day 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 prizes.

Hemingway Days Caribbean Street Fair on Duval Street, July 24 at 10 a.m.

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 and ethnic food, drinks, and original arts and crafts booths. The street fair attracts over 150,000 locals and visitors.

Running of the Bulls on Duval @ Sloppy Joe’s, July 24 at 1 p.m.

This is one of our favorites. Every year the Papa look-alikes from years past return to Key West for the “Running of the Bulls” on Duval 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 Duval. It’s definitely a sight to see. Grab a daiquiri and join in on the fun.

Hemingway 5K Sunset Run and Paddleboard Race, July 24

Test your skills and celebrate Hemingway’s sporting lifestyle during the Hemingway 5K Sunset Run and Paddleboard Race. Meet at Sea, Key West at 3 p.m. to register and celebrate with appetizers, local beer, and a movie. The paddleboard race begins at 5 p.m. from Southernmost Beach, while the 5K begins at 7:30 p.m. from Truman Waterfront Park. Ease your muscles with a post-dace recovery yoga session at Truman Waterfront the following morning at 9 a.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, which offers free hourly shuttle service to 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.

Now for a limited time, The Gates is offering a special Hemingway House Package which gets you inside the Pulitzer Prize-winning author’s tranquil studio, home, and gardens where Hemingway penned some of his greatest novels and stories. You'll also see living descendants of the legendary original six-toed cats! Read more.

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