Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

key west half marathon

Key West Half Marathon & Runfest Weekend

Jan 16 2025 - 7:00am to Jan 20 2025 - 5:00pm
The Annual Key West Half Marathon & 5k is a "bucket list" race.Read more
Races
southernmost regatta

The Southernmost Regatta

Jan 20 2025 - 7:00am to Jan 25 2025 - 7:00pm
January 20 - 25, 2025 Key West The Southernmost Regatta Website Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and...Read more
Upcoming Events
mile 0 fest

Mile 0 Fest

Jan 21 2025 - 7:00am to Jan 25 2025 - 11:00pm
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene.Read more
Festivals
key west songwriters festival

Key West Songwriters Festival

Apr 30 2025 - 7:00am to May 4 2025 - 11:30pm
SAVE THE DATE!! 29th Annual Key West Songwriters Festival April 30 - May 4, 2025Read more
Upcoming Events
key west pride

Key West Pride

Jun 22 2025 - 8:00am to Jun 29 2025 - 5:00pm
June 22 - 29, 2025 Key West KEY WEST PRIDE WEBSITE Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to...Read more
Upcoming Events