Festivals

key west food and wine fest

Key West Food & Wine Festival

Jan 28 2026 - 11:00am to Feb 1 2026 - 10:00pm
When: January 28-February 1, 2026 Where: Restaurants, resorts, and venues across Key West Tickets/Admission Cost: Ticketed tastings, dinners, and events (prices vary) See More Key West Events Frequently Asked Questions: Key West Food & Wine Festival Are all events ticketed? Yes, most tastings, dinners, and...Read more
Festivals
conch republic days

Conch Republic Days

Apr 17 2026 - 2:00pm to Apr 26 2026 - 2:00pm
Only in Key West will you find a festival celebrating the island’s tongue-in-cheek “secession” from the U.S. Conch Republic Days bring parades, lively parties, quirky competitions, and plenty of island pride. t’s a uniquely Key West experience you won’t find anywhere else. Conch Republic Days...Read more
Festivals
key west songwriters festival

Key West Songwriters Festival

Apr 29 2026 - 2:00pm to May 3 2026 - 2:00pm
Each May, Key West turns into a giant music stage as the Songwriters Festival takes over bars, beaches, and theaters. From intimate sets to lively street performances, you’ll hear top songwriters share the stories and sounds behind their biggest hits. When: April 29-May 3, 2026...Read more
Festivals
hemingway lookalike contest

Hemingway Days

Jul 22 2026 - 10:00am to Jul 26 2026 - 10:00pm
Brief Event Description: Hemingway Days celebrates the life and legend of Key West’s most famous resident. From the iconic Hemingway Look-Alike Contest to deep-sea marlin fishing tournaments and literary readings, this July event blends history, sport, and fun. When: July (annually around Hemingway’s birthday) Where:...Read more
Festivals