Hemingway Days 2026
Hemingway Days 2026 at Sloppy Joe’s Bar & Duval Street
Hemingway Days 2026 returns to Key West, Florida, from July 22–26, 2026, celebrating the life, spirit, and legacy of Ernest Hemingway with five days of unforgettable island traditions. Hosted across iconic venues including Sloppy Joe’s Bar, Duval Street, and the Hemingway Home & Museum, this 45th annual festival blends literature, fishing, sport, cocktails, and humor into one of Key West’s most beloved summer events.
Tuesday, July 22, 2026 — Opening Night
The festival begins with a Welcome Happy Hour at Hemingway Distillery, where Papa’s Pilar rum flows as contestants and fans gather. Social club meetups follow, setting the stage for a spirited week.
Wednesday, July 23, 2026 — Papas Take the Stage
Sloppy Joe’s Bar hosts the first round of the Hemingway Look-Alike Contest, complete with live music, scholarship presentations, and auctions. Guests can also mingle with past winners during the afternoon meet-and-greet.
Thursday, July 24, 2026 — Island Flavors & Stories
At the Key West Cooking School, food lovers enjoy a Hemingway-themed feast. Meanwhile, book signings and rum tastings at the Hemingway Social Club celebrate Papa’s literary and adventurous side. The night closes with Round Two of the Look-Alike Contest at Sloppy Joe’s.
Friday, July 25, 2026 — Fishing & Festivities
Papa’s Fish-Off unfolds at the Conch Republic Seafood Co. docks, where contestants cast lines with traditional Cuban Yo-Yos. Evening highlights include a silent auction and more rounds of the Look-Alike Contest at Sloppy Joe’s.
Saturday, July 26, 2026 — Papa’s Big Day
Duval Street comes alive with the Caribbean Street Fair, benefiting Literacy Volunteers of America. The playful Running of the Bulls parade follows, featuring wooden bulls and costumed Papas. The night concludes with the Final Round of the Look-Alike Contest at Sloppy Joe’s, where the 2026 “Papa” is crowned.
Sunday, July 27, 2026 — Birthday & Farewell
The festival wraps up with Papa’s Birthday Bash at Sloppy Joe’s Bar, complete with cake and Bloody Marys. A lighthearted Beach N’ Beer Mile at Southernmost Beach Café and a lively closing pool party at Blue Flamingo Resort give one last toast to Papa.