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 lighting

Lighting of the Key West Harbor Walk of Lights

Nov 27 2024 - 5:00pm
November 27 Key West Lighting of the Key West Harbor Walk of Lights Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2024 Key West Harbor Walk of Lights with lights and creative displays reflecting...Read more
Holiday Events
key west belighted bike ride

Holiday Village and Belighted Bike Ride

Dec 6 2024 - 8:00pm
The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages. The Holiday Village will feature over 20 community booths offering games and activities, carnival rides, bounce houses,...Read more
Holiday Events

Key West Holiday Parade

Dec 7 2024 - 7:00pm
December 07 Key West Key West Holiday Parade Website Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off...Read more
Holiday Events
key west lighted boat parade

Schooner Wharf Bar Lighted Boat Parade

Dec 14 2024 - 8:00pm
December 14 Key West Schooner Wharf Bar Lighted Boat Parade Website Don't miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from...Read more
Holiday Events

Key West Triathlon

Dec 15 2024 - 7:30am
December 15 Key West Key West Triathlon Website The Key West Triathlon begins and ends at College of the Florida Keys, 5901 College Rd., shifting from the traditional location because of ongoing construction along S. Roosevelt Avenue. All fitness levels are welcomed. Races include the...Read more
Holiday Events
Nutcracker

Nutcracker Key West

Dec 5 2024 - 7:30pm to Dec 15 2024 - 7:30pm
December 05 - 15, 2024 Key West Nutcracker Key West Website Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens,...Read more
Holiday Events

Old Town Trolley: Holiday Nights Tours

Dec 9 2024 - 7:45pm to Dec 23 2024 - 7:45pm
December 09 - 23, 2024 Key West Old Town Trolley: Holiday Nights Tours Website Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated...Read more
Holiday Events
key west waterfront winter wonderland

KEY WEST WATERFRONT WINTER WONDERLAND

Dec 13 2024 - 9:00am to Dec 28 2024 - 8:00pm
December 13 - 28, 2024 Key West Waterfront Winter Wonderland Website Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with an ice-skating, rides, games, music, holiday lights,...Read more
Upcoming Events
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