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. 

Mango Fest Key West

Jun 25 2020 - 1:00pm to Jun 28 2020 - 1:00pm
The 4th Annual Mango Fest in Key West has been dubbed the "Best Mango Festival in the World!" From mango tastings to mango daiquiris, this event has it all.Read more

Hemingway 5k Sunset Run & Paddleboard Race

Jul 25 2020 - 5:00pm
It's the 31st anniversary of the Hemingway 5k Run/Walk and Paddleboard Race. The competitions are part of Hemingway Days. Paddleboard Race Details Begins at 5:30 p.m. Starts and finishes at Southernmost Beach (1205 Duval St) 3-mile ocean course 5k Run/Walk Details Begins at 7:30 p.m...Read more

Hemingway Days

Jul 21 2020 - 10:00am to Jul 26 2020 - 8:00pm
The 40th Annual Hemingway Days festival celebrates and honors Ernest Hemingway, who lived and wrote in Key West during the 1930s. The event brings fans, writers, anglers, and look-alikes Key West. Be sure to visit the Ernest Hemingway Home & Museum (907 Whitehead St.) where...Read more
Colored Baskets

Bahama Village Goombay Festival

Oct 16 2020 - 12:00pm to Oct 17 2020 - 11:45pm
Held in Key West's historic Bahama Village neighborhood, the lively, family-friendly Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West's Bahamian heritage. FREE event, noon to...Read more
Key West Fantasy Fest

Key West Fantasy Fest

Oct 16 2020 - 8:00am to Oct 25 2020 - 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

Key West Half Marathon

Jan 17 2021 - 7:00am
The 23th Annual Key West Half Marathon & 5k is a "bucket list" race. All participants receive awesome race shirts and finisher medals, custom bib and race bag, and will enjoy live music throughout the course, concert at the Awards Ceremony, drink and food specials,...Read more
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Jan 16 2021 - 8:00am to Jan 17 2021 - 8:00pm
Save the dates for the Annual Florida Keys Seafood Festival in Key West January 16 & 17, 2021 for the freshest seafood caught, cleaned, prepared & served by your local fisherman. $5 admission good for BOTH Saturday & Sunday. This event is a fundraiser for...Read more