Hemingway Days & Hemingway Look-Alike Contest

Key West comes alive with Hemingway Days, a spirited five-day festival celebrating the life, legacy, and island era of Ernest “Papa” Hemingway. The event blends literary homage with playful contests, waterfront competition, and lively street festivities that draw fans, writers, anglers, historians, and curious travelers alike.

At the heart of the festivities is the iconic Hemingway Look-Alike Contest, where bearded entrants attempt to channel “Papa” through appearance, personality, and presence. Alongside it, the Running of the Bulls offers a whimsical twist on a Spanish tradition—contestants parade with wooden “bulls” through the streets of Old Town. The Key West Marlin Tournament brings serious anglers to the waters for high-stakes sport fishing, while a diverse literary program includes short-story contests, readings, and book events.

The festival also features a Caribbean Street Fair infused with local arts, food, and music, and the Papa’s Birthday Bash caps off the week with cake, cocktails, and celebration at historic Sloppy Joe’s Bar. Through its mix of competition, culture, and community, Hemingway Days captures the adventurous spirit of Hemingway himself—and invites visitors to walk in the footsteps of a literary giant under the tropical skies of the Florida Keys.