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 paddle classic


Oct 1 2022 - 12:00am
October 1 Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker,...Read more
legends of music row music festival

Legends Of Music Row Music Festival

Oct 13 2022 - 3:30pm to Oct 15 2022 - 11:30pm
Book your tickets for this extraordinary three-night event, including an option for a VIP experience with an exclusive, up-close-and-personal concert setting featuring songwriting legends in country music. A musical experience like no other, Legends of Music Row is to be hosted by Country Music Hall...Read more
goombay festival

Goombay Festival

Oct 21 2022 - 10:00am
This year’s Key West Goombay Festival will take place October 21 & 22, 2022 Let’s all get together and celebrate.Read more
Fantasy Fest 2022

Fantasy Fest Key West 2022

Oct 21 2022 - 8:00am to Oct 30 2022 - 5:00pm
Started in 1979 by Key West Locals, this 10-day parade has turned into one of the best and biggest parties Key West has to offer!Read more
Race World Offshore Championship

Race World Offshore - Key West Championships

Nov 6 2022 - 10:00am to Nov 13 2022 - 11:15pm
Photo Courtesy of Race World Offshore Facebook Race World Offshore returns to Key West for an amazing championship event. Five days of preparation and events (Sunday - Thursday) will precede three days of racing (Friday - Sunday). This is a great event for spectators. High-speed...Read more
key west at christmas

Lighting of the Bight- Key West Harbor Walk of Lights

Nov 25 2022 - 6:00pm
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2020 Key West “Harbor Walk of Lights” with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme! The...Read more
key west christmas tree

Lighting of the Holiday Tree

Nov 29 2022 - 6:00pm
The Lighting of the Holiday Tree is November 29, 2021 in Bayview Park, 1320 Truman Ave Key West FL 33040 at 6:00 PM. Make the most of the holidays and find the perfect key west vacation rental with us to accommodate your stay!Read more
key west bikes

Key West Lighted Bike Ride

Dec 2 2022 - 4:00pm
Key West BeLighted Bike Ride sponsored by Coca Cola Beverages Florida Friday, December 3rd, 4– 8pm BeLighted Holiday Village at Coffee Butler Amphitheater inside Truman Waterfront Park. BeLighted Bike Ride leaves at 8pm Entry for the bike ride is an unwrapped toy or monetary donation...Read more
key west lighted boat parade

Schooner Wharf Bar Lighted Boat Parade

Dec 10 2022 - 8:00pm
Schooner Wharf Bar hosts the lighted boat parade every year. It is a crowd favorite for sure. This family fun event starts early (plan 6pm). Head over and enjoy a stroll through the Historic Seaport, shopping the stores and tasting the wonderful food from the...Read more
Key West Half Marathon and 5K

Key West Half Marathon

Jan 13 2023 - 7:00am
The 24th Annual Key West Half Marathon & 5k is a "bucket list" race.Read more