Key West Florida Weekly

Being Ernest: Hemingway Days return in July

Former Hemingway Look-Alike Contest winners serve as judges in the annual competition. COURTESY PHOTO

Former Hemingway Look-Alike Contest winners serve as judges in the annual competition. COURTESY PHOTO

The 41st Hemingway Days light up Key West for a six-day commemoration from July 19 to 24.

Hemingway Days in Key West celebrates the literary success but also the colorful lifestyle of Ernest Hemingway.

Every year, to celebrate Hemingway’s birthday (July 21, 1899) and to honor his contributions to the fabric of America, Key West comes to life with lively literary events including the Hemingway with a look-a-like contest, a 5k run, and paddleboard race, and a three-day marlin tournament.

Hemingway lived in Key West for most of the 1930s and he wrote “For Whom the Bell Tolls,” “Death in the Afternoon” and “To Have and Have Not” in tiny writing studio in his home on Whitehead Street, now a registered National Historic Landmark and a museum. The site is almost as well-known for its polydactyl cats as for its literary maverick.

Here’s a summary of major events around town. Info:

Havana Club Key West Marlin Tournament — Wednesday-Saturday, July 20-23. This tournament, held annually since 1982 (with a few misses), celebrates Hemingway’s love of sea-fishing and the sea. Registration is limited to 75 boats which are angling for $50,000 in cash prizes. The event features cocktail parties, dinners, and an award banquet.

Hemingway Look-Alike Contest — Thursday-Saturday, July 21-23, at Sloppy Joe’s Bar, 201 Duval St., Key West. Hosted by the Hemingway Look-Alike Society, the preliminary rounds are limited to 80 stocky, white-bearded contestants, who can only register one night. Each night the judges will select approximately 12 semi-finalists to advance to the final round. Contestants pre-register by mail through July 14. email


¦ Meet the “Papas” at Sloppy Joe’s —5:30 p.m. Wednesday. Get to know the contestants and previous winners of “Sloppy Joe’s Hemingway Look-Alike Contest.

¦ Sing Papa Happy Birthday with cake — 5:30 p.m. Thursday at Sloppy Joe’s Bar.

¦ Hemingway Look-Alike Society scholarship presentations — 6 p.m. Thursday. The winners of its annual scholarships for Florida Keys students will be announced on stage.

¦ Round One of the Hemingway Look-Alike Contest — 6:30 p.m. Thursday.

¦ Round Two — 6:30 p.m. Friday.

¦ Photos with “Papas” — Noon Saturday. Hemingway Look-Alikes provide a photo opportunity for fans outside Sloppy Joe’s on Greene St.

¦ Running of the Bulls — 1 p.m. July 23. Past “Papa” Hemingway Look-Alike Contest winners dressed in their Pamplona best cause chaos on Greene St. outside Sloppy Joe’s.

¦ Hemingway Look-Alike Contest Final Round — 6:30 p.m. July 23. “Papa 2022,” the winner of the Hemingway Look-Alike contest, is crowned.

Hemingway 505 Bike Ride — 9 a.m. July 23, from Marathon to Key West. This new race starts at the beach on Sombrero Road in Marathon and has scheduled stops at Little Torch Key off of Barry Road and Baby’s Coffee in Key West before it crosses the finish line at Key West Waterfront Park. Register at

Hemingway Paddleboard Race — 5:30 p.m. July 23 on Southernmost Beach (1405 Duval St. on the Atlantic Ocean), and Old Town Key West. Paddleboarders navigate a 3-mile course that finishes back at the beach. $59.

Hemingway 5k Sunset Run/Walk — 7:30 p.m. July 23 beginning at the Southernmost Point in the continental United States, on the oceanfront at Whitehead and South Street. The course is a flat 3.1- mile route through Old Town past local landmarks, including the Ernest Hemingway Home & Museum, the Green Parrot Bar, the Key West Lighthouse, and the Custom House.

The entry fee ($59 plus $4.42 sign-up fee before June 26, $65 after, includes a collectible race tech shirt, chip timing, custom bibs, food, finisher medals, libations, and lots of great giveaways. Runners and paddleboarders can register online at or download registration at

Registration race day from 3-7 p.m. on the beach outside of the Southernmost Beach Café. Race packets, bibs, and shirts can be picked up there. They’ll also have collectible race tech shirts. A post-race awards beach party with live music and free food takes place after the race.

Don’t miss these extra offerings:

¦ Fuel up at Sea, a free Pre-Race Power Brunch — 11 a.m.-2 p.m. race day at Sea, Key West, 720B Caroline St. Also, 20 percent discount on store purchases.

¦ Post-Race Recovery Yoga — 8:45- 9:45 a.m. at The Perry Hotel & Marina Key West by salute to the sol.

¦ The Hemingway Pub Crawl — Noon-3 p.m. July 24. The “Smile Mile” features visits at several local bars for drinks and souvenirs and last stop party at Rams Head Southernmost, 804 Whitehead St. Register at ¦

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