Hemingway Days
When: July 22 - July 26, 2026
Where: Duval St, Key West, FL 33040
Discover Hemingway Days in Key West: Celebrate Literature, Culture, and Island Fun
Experience the vibrant spirit of Key West during the annual Hemingway Days celebration, happening July 22–26, 2026. This iconic festival honors literary giant Ernest Hemingway, who spent the 1930s crafting masterpieces in this tropical paradise. Visitors will enjoy an exciting lineup of events, including the legendary Hemingway Look-Alike Contest at Sloppy Joe’s Bar, a fun-filled Running of the Bulls, and a thrilling Key West Marlin Tournament offering cash prizes and drawing competitors from around the globe to the Perry Hotel and Marina.
Literature enthusiasts can explore Hemingway’s world through daily tours at the historic Hemingway Home & Museum on Whitehead Street and participate in the renowned Lorian Hemingway Short Story Competition, awarding talented writers since 1981.
Join the excitement starting Wednesday, July 23, at the "Meet & Greet the Papas" gathering at Sloppy Joe’s, or start your day on Thursday, July 24, with "Coffee and Donuts with the Papas" at Southernmost Pint Brewpub. Each evening, cheer on contestants competing in Sloppy Joe's lively Look-Alike Contest, featuring auctions benefiting scholarships for students at The College of the Florida Keys.
Don’t miss Friday’s quirky Papa Hemingway Look-Alike Fish-Off at Conch Republic Seafood Company, featuring a spirited Cuban-style fishing challenge. Saturday brings the Caribbean atmosphere alive with the Caribbean Street Fair on famous Duval Street, offering local artisan goods, delicious food, and family-friendly entertainment. The quirky annual tradition, the humorous Running of the Bulls, will delight audiences as "bulls" chase the Hemingway look-alikes along Greene Street.
The celebration concludes Sunday, July 27, with the festive Papa Birthday Bash at Sloppy Joe's featuring birthday cake, photo ops, and Bloody Marys with Hemingway look-alikes. Later, savor Key West's cocktail culture during the Hemingway Rum Bar Stroll, presented by Papa's Pilar Rum, visiting eight vibrant locations, each serving a signature rum drink.
Whether drawn by world-class fishing, unique cultural events, or literary festivities celebrating Hemingway's legacy, Hemingway Days in Key West promises an unforgettable tropical getaway. For full event details, visit KeyWestLookalikes.com.
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