Hemingway Days

When: July 20 - July 22, 2023

Where: Duval St, Key West, FL 33040


Key West will see a multitude of bearded Hemingway lookalikes, and fans of Ernest Hemingway's writing and life, during Hemingway Days 2023, which runs from Wednesday to Saturday, July 19-22.

The festival's most popular event is the Hemingway Lookalike Contest at the Sloppy Joe Bar on Duval Street, which the writer frequented during his Key West residency in the 1930s.

The Hemingway Days schedule also features the Stock Island Marina Village Key West Marlin Tournament and the 5k Sunset Run/Walk and Paddleboard Race, both saluting Hemingway’s sporting lifestyle, and a lively daylong street fair on famed Duval Street.

SCHEDULE OF EVENTS

WEDNESDAY, JULY 19

4 PM: Final registration for the Perry Hotel & Marina Key West Marlin Tournament, now in its 41st year. Anglers compete for $50,000 in guaranteed cash prizes for targeting marlin, spearfish, sailfish, dolphin fish, tuna and wahoo. Tournament tent at the Perry Hotel & Marina, 7005 Shrimp Road. Visit keywestmarlin.com.

5:00 PM: Meet the “Papas.” Get to know the contestants and previous winners of Sloppy Joe’s Hemingway® Look-Alike Contest. Sloppy Joe’s Bar, 201 Duval St.

6-8 PM: Key West Marlin Tournament captains meeting, reception, auction and raffle. Tournament tent at the Perry Hotel & Marina.

THURSDAY, JULY 20

8:30 AM to 4 PM: 41st annual Key West Marlin Tournament’s first day of fishing. Visit keywestmarlin.com.

4-6 PM: Key West Marlin Tournament weigh-in at the Stock Island Marina Village.

6:00 PM: Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. On stage at Sloppy Joe’s Bar.

6:30 PM: Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round.

FRIDAY, JULY 21

8:30 AM to  4 PM: 41st annual Key West Marlin Tournament’s second day of fishing.

4-6 PM: Key West Marlin Tournament weigh-in at the Stock Island Marina Village.

6:30 PM: Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round.
 
SATURDAY, JULY 22

8:30 AM to  3 PM: 41st annual Key West Marlin Tournament’s final day of fishing.
 
Noon: Photos with “Papas.” Hemingway® Look-Alikes provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s.

1:00 PM: Running of the Bulls. This wacky event is sponsored by Sloppy Joe’s Bar and features past “Papa” Hemingway® Look-Alike Contest winners dressed in their Pamplona best — and a breed of “bull” found only in Key West.  The fun takes place on Greene street outside Sloppy Joe’s.

3-5 PM: Key West Marlin Tournament weigh-in at Stock Island Marina Village.

3-7 PM: 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. $65 entry fee for run/walk;  $65 entry fee for paddleboard race. Visit keywesthalfmarathon.com.

5:30 PM: 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 keywesthalfmarathon.com.

6:30 PM: Sloppy Joe’s 42n Annual Hemingway® Look-Alike Contest – FINAL ROUND to name Papa 2023.

7:30 PM: 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. Visit keywesthalfmarathon.com.

This is a preliminary schedule and is subject to change.

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