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Hemingway Days at Key West

Are you ready for the legendary Hemingway Days? Because at Key West we are!

This HUGE annual celebration is almost here. We're getting ready to honor the legacy of Hemingway, the American literary giant who dedicated his life to writing, who spent most of the 1930's here in Key West!

Step into an experience and write your own story here at the Key West. You can participate in many events, such as our own version of Running with the Bulls, fishing tournaments, and more. If you're feeling adventurous, you can even join the Paddleboard Race. In this great event, there's something for everyone.

Make sure you come ready to have fun & get rowdy! Join the fun; it only happens once a year!


2019 Hemingway Days, July 16-21, Schedule of Events


9:30 a.m. to 4:30 p.m.      “Hemingway Collection” museum days at the Custom House. 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 that provide a visual narrative to Hemingway’s “The Old Man and the Sea.” Custom House Museum, 281 Front St. Free entry to those who mention Hemingway Days at the admission desk. Visit 


6-8 p.m.           Key West Art & Historical Society’s Hemingway Days Mini-Symposium. The symposium features scholars and writers inspired by Hemingway’s work. Presenters are moderator Kirk Curnutt, Ph.D., outlining Hemingway’s little-known first attempt to fictionalize Key West; Brewster Chamberlin, Ph.D., discussing Key West during Hemingway’s era; and Robert K. Elder, unveiling 99-year-old Hemingway letters. Old City Hall, 510 Greene St. Registration required; $5 per person (free for KWAHS members). Visit


4 p.m.              Final registration for the Stock Island Marina Village Key West Marlin Tournament. Anglers compete for $50,000 in guaranteed cash prizes for targeting marlin, spearfish, sailfish, dolphin fish, tuna and wahoo. Tournament tent at Stock Island Marina Village, 7005 Shrimp Road. Visit

5-7 p.m.           “Voices, Places, Inspirations.” This evening of readings and presentations begins with “Papa’s Poems,” presented by members of the acclaimed Key West Poetry Guild. Subsequent presenters are Kirk Curnutt, discussing notable novels about Key West and their writers; Kristina Neihouse, presenting her first novel, “Knowing When to Leave”; and Edgardo Alvarado-Vazquez, sharing excerpts from his prose and poetry books. A talk back and book signing follow. Old City Hall. Free admission. 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. Tournament tent at Stock Island Marina Village.


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 at Stock Island Marina Village.

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 39th 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 island-style pig roast and cocktails. Tournament tent at Stock Island Marina Village.


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

11:15 a.m. &  12:15 p.m.    “Hemingway: Between Key West and Cuba” film screening. A film by Richard Abella, this intriguing documentary examines the two islands whose cultures and people shaped Ernest Hemingway’s life and writing for more than three decades. The showing features a Q & A session with executive producers and writers C. Michael Curry and Raul Villarreal. Tropic Cinema, 416 Eaton St. $5 per person; tickets must be purchased through Tropic Cinema:

1 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 at Stock Island Marina Village.

6:30 p.m.         Sloppy Joe’s 39th 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 dockside cocktails and fish fry. Tournament tent at Stock Island Marina Village.


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. Several 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. 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. A festival tradition, 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 pre-birthday party for “Papa.” Salute Ernest’s July 21 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 at Stock Island Marina Village.

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. Outside Southernmost Beach Café, 1405 Duval St. $50 entry fee for run/walk, $45 for paddleboard race or $90 for both. Visit

5:30 p.m.         Paddleboard Race begins. Competitors follow a 3-mile Atlantic Ocean course that begins and ends at Key West’s Southernmost Beach, 1405 Duval St. 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 39th 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

Earlier Event: June 28
Key West Mystery Writer's Fest
Later Event: August 8
Key West Lobsterfest 2019