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

Key West Paddle Classic

Oct 3 2020 - 7:00pm
*New Date for 2020! The Key West Paddle Classic is an annual event where competitors circumnavigate the island of Key West. The 12-mile course can be covered individually or divided among a 3-person team. There are divisions among the various vessels, which include stand-up paddleboards,...Read more
Key West Songwriters Festival

Key West Songwriters Festival

Oct 7 2020 - 4:45pm to Oct 11 2020 - 4:45pm
The annual showcase of musical magic features America's foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The largest festival of its kind in the world celebrates 24 years as both a tourist attraction and favorite of island locals. The festival revolves around...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
Race World Offshore Championship

Race World Offshore - Key West Championships

Nov 8 2020 - 7:15pm to Nov 15 2020 - 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
Conch Republic Flag

Annual Conch Republic Independence Celebration

Nov 27 2020 - 8:00am to Dec 6 2020 - 6:00pm
With activities such as a lighthearted sea battle featuring tall ships, the Conch Republic's 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys. The event normally takes place in the early spring but in 2020 will take place in early...Read more
Key West Half Marathon and 5K

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
Key West 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