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Key West Time
October 16th
11:31pm · 81°F

Hemingway Days Celebration 2018

38th Annual Hemingway Days to Honor Ernest July 17-22, 2018

The festival celebrating Key West favorite literary royalty, Ernest Hemingway, begins this week. This celebration of the late writer takes place through the week with various events around town starting on the 17th.

This almost week long event draws a crowd from near and far. The highlight of the happening is the annual Hemingway Look-a-like Contest. The "Running of the Bulls" is another Key West locals favorite. Featuring a troop of Hemingway look-a-likes parading down Duval with a herd of paper and cardboard bulls in chase. For information on other event and for time and location, see the complete schedule listed below.

hemingways fishing Hemingway Look-a-likes at the annual fishing contest.

Hemingway days 2018 Schedule Of Events:


9:30 a.m. to  4:30 p.m.     “Hemingway Collection” Museum Day. Discover rare artifacts and memorabilia from Hemingway’s life, a life-sized bronze of the author and 59 original pen-and-ink drawings by famed marine wildlife artist Guy Harvey — all illustrating Hemingway’s “The Old Man and the Sea.” Custom House Museum, 281 Front St. Free admission for Hemingway Days participants. Visit 

6-8 p.m.           Key West Art & Historical Society’s Hemingway Symposium. The symposium features scholars, actors and writers inspired by Hemingway’s work. Presenters are moderator Kirk Curnutt, Ph.D., author of “Coffee with Hemingway” among others; Ashley Oliphant, Ph.D., author of “Hemingway and Bimini: The Birth of Sport Fishing at ‘The End of the World’”; Brewster Chamberlin, Ph.D., discussing Key West during Hemingway’s era; actor and playwright Brian Gordon Sinclair, author of the multi-volume series “The Hemingway Monologues”; and writer Cristen Hemingway Jaynes, Hemingway’s great-granddaughter. Old City Hall, 510 Greene St. Registration required; $5 per person (free for KWAHS members). Visit



4 p.m.              Final registration for the Havana Club Key West Marlin Tournament. Anglers compete for $50,000 in guaranteed cash prizes for targeting marlin, spearfish, sailfish, dolphin fish, tuna and wahoo. Waterfront Brewery, 201 William St. Visit

5:30 p.m.         Meet the “Papas.” Get to know the contestants and previous winners of Sloppy Joe’s Hemingway® Look-Alike Contest. Sloppy Joe’s, 201 Duval St. Visit

6-8 p.m.           Key West Marlin Tournament captains meeting, auction and raffle. Waterfront Brewery, upstairs deck.

7:30-9 p.m.     “Voices, Places, Inspirations.” This evening of readings, presentations and storytelling features Chuck Ball, author of “Last Chance Key West” among others; Cristen Hemingway Jaynes, reading from “The Mirage of Mario Sanchez”; Kirk Curnutt, discussing notable novels about Key West and their writers; Brewster Chamberlin, whose books include “Peregrine’s Island”; and Brian Gordon Sinclair, author of “The Hemingway Monologues” among others. A “meet-the-authors” reception follows. Key West Lighthouse and Keepers Quarters. 938 Whitehead St. Free admission. Visit


8:30 a.m. to 4 p.m. Key West Marlin Tournament’s first day of fishing. Visit

4-6 p.m.           Key West Marlin Tournament weigh-in. Dock outside Waterfront Brewery.

6 p.m.              Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. Onstage at Sloppy Joe’s Bar. Visit

6:30 p.m.         Sloppy Joe’s 38th annual Hemingway® Look-Alike Contest, first preliminary round, to be judged by former contest winners. Sloppy Joe’s Bar. $35 entry fee. Free to watch. Visit

6:30-8 p.m.   Key West Marlin Tournament cocktail party and island-style pig roast. Waterfront Brewery, upstairs deck. Free to tournament participants.

7:30-9 p.m.     “The Hemingway Monologues” hosted by Brian Gordon Sinclair. Attendees can view the film “The Hemingway Monologues: Life and Death in Key West,” narrated by playwright and actor Sinclair, and discover his seven-volume series “The Hemingway Monologues: An Epic Drama of Love, Genius and Eternity.” Co-hosted by Cristen Hemingway Jaynes, the event includes Canada’s Hemingway on Stage Award presentation. Tropic Cinema, 416 Eaton St. $5 per person (free for KWAHS members). Visit




8:30 a.m. to  4 p.m.   Key West Marlin Tournament’s second day of fishing.

1:30 p.m.            “Papa” Look-Alike Fish-Off. Cheer your favorites as the “Papas” compete in this dockside catch-and-release challenge using traditional “Cuban yo-yos” at Conch Republic Seafood Co. docks, 631 Greene St. Free to watch.

4-6 p.m.           Key West Marlin Tournament weigh-in. Dock outside Waterfront Brewery.

5:30 p.m.         “Papa’s Poems.” The Key West Poetry Guild presents a reading of the poetry of Ernest Hemingway, as well as their own work, during a free-admission event at Key West’s Old City Hall. For info, contact Nance Boylan at 908-591-5566. 

6:30 p.m.         Sloppy Joe’s 38th annual Hemingway® Look-Alike Contest, second preliminary round, to be judged by former contest winners. Sloppy Joe’s Bar. $35 entry fee. Free to watch. 

6:30-8 p.m.     Key West Marlin Tournament cocktail party and fish fry. Waterfront Brewery, upstairs deck. Free to tournament participants.

8:30-11 p.m.   Key West Marlin Tournament party with the Havana Club team. Enjoy an exuberant gathering for tournament participants.


8:30 a.m. to  3 p.m.      Key West Marlin Tournament’s third day of fishing.

10 a.m.  to 10 p.m.       Caribbean Street Fair presented by Literacy Volunteers of America–Monroe County. Four blocks of Key West’s famed Duval Street, beginning at Front Street, are closed to vehicular traffic and transformed into an open-air island market with arts, crafts, jewelry, tropical clothing and food. Visit or email

Noon                Photos with “Papas.” Look-alikes provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s. For info, visit

1 p.m.              Running of the Bulls. Now in its 20th year, this wacky event is sponsored by Sloppy Joe’s Bar and features Hemingway® Look-Alike Contest winners and entrants dressed in their Pamplona best — and a breed of “bull” found only in Key West. The fun starts on Greene Street outside Sloppy Joe’s. Visit

1:30 p.m.         Sloppy Joe’s birthday party for “Papa.” Celebrate Ernest’s birthday (complete with cake) alongside former winners and contestants in the Hemingway® Look-Alike Contest. Greene Street outside Sloppy Joe’s Bar.

3-5 p.m.           Key West Marlin Tournament weigh-in. Dock outside Waterfront Brewery.

3-7 p.m.           Hemingway 5k Sunset Run/Walk and Paddleboard Race registration. Register and pick up race packets for the popular run and paddleboard challenge. Southernmost Beach Café, 1405 Duval St. $45 entry fee for either race or $85 for both. Visit

5:30 p.m.         Lazy Dog Paddleboard Race. Competitors follow a 3-mile Atlantic Ocean course that begins and ends at Key West’s Southernmost Beach, 1405 Duval St. on the ocean. Visit

6:30 p.m.         Key West Marlin Tournament awards banquet and silent auction. Cocktails and silent auction are set for 6:30 p.m., with the dinner and awards presentations at 7:30. Open to tournament participants and their guests only. Margaritaville Key West Resort & Marina, 245 Front St.

6:30 p.m.         Sloppy Joe’s 38th annual Hemingway® Look-Alike Contest, final round, to be judged by former contest winners. Sloppy Joe’s Bar. Free to watch.

7:30 p.m.         Hemingway 5k Sunset Run/Walk. Racers start at the Southernmost Point in the continental United States at Whitehead and South streets, and proceed through Old Town Key West. A post-race awards party is scheduled at the Southernmost Beach Café. Visit


10 a.m.                        Bloody Marys with “Papa.” Start the day at Sloppy Joe’s. Visit

10 a.m.           Sloppy Joe’s Arm Wrestling Contest. Registration is set for 10 a.m. and the contest begins at 11 a.m. Prizes await winners in multiple weight divisions. Sloppy Joe’s Bar. $5 entry fee; free to watch. Visit

12-2 p.m.        Hemingway’s Key West by Trolley. Historian Sharon Wells leads a trolley tour of sites associated with Hemingway’s Key West years, including his former home and waterfront settings he memorialized in his novel “To Have and Have Not.” $10 per person ($5 for KWAHS members). Meet at the Custom House Museum. Visit

3 p.m.              Lorian Hemingway Short Story Competition winners’ announcement. Author Lorian Hemingway, Ernest’s granddaughter, will announce the winners of her internationally recognized fiction contest online at A $1,500 cash prize and publication await the first-place winner.

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