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. 

mile 0 fest

Mile 0 Fest

Apr 27 2021 - 7:00am
Party with your favorite Red-Dirt and Americana bands in Paradise at Mile 0 Fest Key West, April 27thRead more
Key West Songwriters Festival

Key West Songwriters Festival

May 5 2021 - 7:00am to May 9 2021 - 11:30pm
The Key West Songwriters Festival -the largest festival of its kind in the world. Celebrating its 25th year. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The...Read more
key west whiskey fest

Key West Whiskey Festival

May 27 2021 - 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 blues festival

2nd Annual Key West Blues Festival

May 29 2021 - 8:00pm
SAT MAY 29, 2021 - 8:00 PM Ages: 21 & Over Doors Open: 7:00 PM Door Price: $35.00 - $45.00Read more
key west pride

Key West Pride

Jun 2 2021 - 8:00am to Jun 6 2021 - 5:00pm
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair,...Read more
mango fest key west

Mango Fest Key West

Jun 23 2021 - 1:00pm to Jun 27 2021 - 1:00pm
Experience all things Mango through shopping, education and demonstrations. Stroll through Truman Waterfront Park to visit vendors, shop local shops, visit galleries, and order great food.Read more

Key Lime Festival

Jul 1 2021 - 7:00am
Enjoy a full 4 days of culinary events for every taste, including favorites from past years such as the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers like a Key Lime Scavenger Hunt and Key...Read more
key west lobster fest

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

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