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Home Destinations
U.S. Southeast Seaboard Regional Report

Hemingway Look-Alike Contest

U.S. Southeast Seaboard Regional Report

2025

July 5, 2025
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July

Key limes, fishing, and Hemingway Days are all part of the fun.

Key Lime Festival: July 2-5

The Key Lime Festival in Key West is a lively celebration of Florida’s beloved citrus fruit, full of fun and flavorful events. From a bubbly champagne kickoff and cookbook signings to Key lime-inspired meals and hands-on pie-making classes, there’s something for everyone. Don’t miss the wacky pie-eating contest on July 4th, the legendary Key lime pie drop from the lighthouse, a festive 5K run, and plenty of Key lime cocktails and bar crawls to keep the party going.

Hemingway Days: July 22-27

Hemingway Look-Alike Contest

Hemingway Days in Key West is a weeklong celebration honoring the legendary Ernest Hemingway, packed with spirited events and island flair. Fans, writers, and anglers gather for the iconic Hemingway Look-Alike Contest, a playful Key West-style Running of the Bulls, engaging literary talks, and a birthday salute on July 21st. The festivities also include a museum exhibit, marlin fishing tournament, 5K run, paddleboard race, lively street fair, and more.

Key West Marlin Tournament: July 16-23

As part of the 45th Annual Hemingway Days, the Hemingway Fishing Tournament reels in big excitement with $50,000 in guaranteed cash prizes. The top team racking up points for marlin and spearfish takes home a cool $25,000. Anglers can also boost their scores by landing fun catches like tuna, wahoo, and sailfish. Limited to just 75 boats, the action unfolds at Stock Island Marina Village.

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Sloppy Joe’s 44th Annual Hemingway Look-Alike Contest: July 23-27

A highlight of Hemingway Days, the beloved Look-Alike Contest celebrates the larger-than-life spirit of Ernest Hemingway and his ties to Key West. Hosted at his old stomping grounds, Sloppy Joe’s Bar, the fun kicks off with preliminary rounds on July 24th and 25th, leading up to the big finale on Saturday, July 26th, when a new “Papa” is crowned.

Hemingway Days: Running of the Bulls: July 26

One of the quirkiest Hemingway Days traditions, the Running of the Bulls happens right outside Sloppy Joe’s Bar. Past and present Hemingway Look-Alikes suit up Pamplona-style and parade alongside Key West’s own wild take on “bulls.” The action starts at 1PM on Greene Street, and it’s free for everyone to enjoy.

Hemingway 5k Sunset Run & Beach N’ Beer Mile: July 26-27

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The 36th Annual Hemingway 5K Sunset Run starts at the iconic Southernmost Point Buoy in Key West, with registration taking place at the Southernmost Beach Café. After the race, join the beach party for awards, rum and beer tastings, raffles, and live music. The fun continues Sunday with the Beach N’ Beer Mile—a four-beer race kicking off at noon, followed by a costume-friendly pool party at Rum Row from 3-6PM. keywest.com

-by Don LaNeve

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