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 whiskey fest

Key West Whiskey Festival

May 26 2022 - 7:00am
This innaugural food, drink and music festival is one of the most eagerly awaited on Florida Keys’ busy social calendar. Featuring top class whiskey, Popular highlights will include a range of Tastings, Whiskey walks, Workshops, Brunches and plenty more.Read more
key west pride

Key West Pride

Jun 1 2022 - 8:00am to Jun 5 2022 - 5:00pm
Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, a...Read more

Key West Fantasy Fest

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
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