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 tropical heat

Key West Tropical Heat

Aug 11 2021 - 5:00pm
TROPICAL HEAT is Key West’s HOTTEST event for men! The temperature is not the only thing that will rise during Tropical Heat. The all-male theme parties, pool parties, and adult-oriented entertainment promises to be HOT! August on the Island is always HOT, but during Tropical...Read more
key west lobsterfest 2021

25th Annual Key West Lobsterfest

Aug 12 2021 - 8:00am
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate...Read more

Goombay Festival 2021

Oct 22 2021 - 7:30am to Oct 23 2021 - 11:30pm
We are very happy to let everyone know that Goombay 2021 has been approved. Our festival dates are October 22 & 23, 2021 Let the party beginRead more
fantasy fest

Key West Fantasy Fest

Oct 22 2021 - 8:00am to Oct 31 2021 - 5:00pm
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.Read more
Race World Offshore Championship

Race World Offshore - Key West Championships

Nov 7 2021 - 7:15pm to Nov 14 2021 - 7:15pm
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. VISIT...Read more
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