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

Jan 25 2022 - 7:00am to Jan 29 2022 - 11:00pm
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene.Read more
key west food & wine festival

Key West Food & Wine Festival

Jan 26 2022 - 7:30pm to Jan 30 2022 - 7:30pm
The Key West Food and Wine Festival is a series of wine and food themed events, showcasing a diverse range of wines and inventive cuisine, hosted by their passionate creators and iconic Key West locations.Read more

Key West Craft Show

Jan 29 2022 - 7:30pm to Jan 30 2022 - 7:30pm
2022 marks the 36th Annual Key West Craft Show, a 2-day juried outdoor craft festival bringing over 100 fine and skilled craft artists to this historic area of Key West.Read more
kelly mcgillis classic

30th Kelly McGillis Classic International Women & Girls Flag Football Championships

Jan 24 2022 - 8:00am to Jan 31 2022 - 11:00pm
The 30th Kelly McGillis Classic International Women & Girls Flag Football Championships & World Challenge Game are coming back to Key West, Florida - USA! From Jan 27 - 30, 2022 (games only) or Jan 24 - 31 (full week of events: flag football clinics...Read more
key west art & historical society

Hemingway Days

Mar 1 2022 - 10:00am to Mar 31 2022 - 8:00pm
Internationally renowned playwright Tennessee Williams, who lived in Key West for more than 30 years, once said of his chosen home, “I work everywhere, but I work best here.” Fans of Williams’ classic plays can explore his writing and life in the island city. While...Read more
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Apr 2 2022 - 8:00am to Apr 3 2022 - 8:00pm
Save the dates for the Annual Florida Keys Seafood Festival in Key West January 15 & 16, 2022 for the freshest seafood caught, cleaned, prepared & served by your local fisherman. $10 admission good for BOTH Saturday & Sunday. This two day celebration is a...Read more
mote marine ocean fest

Mote Ocean Fest

Apr 23 2022 - 10:00am
Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment! From 10 a.m. to 4 p.m., enjoy an outdoor community celebration of the oceans at Truman Waterfront Park. A day of family activities, raffles, live music, shopping and environmental exhibits are...Read more
Conch Republic Flag

Annual Conch Republic Independence Celebration

Apr 14 2022 - 8:00am to Apr 24 2022 - 6:00pm
Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration, a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol checkpoint...Read more
Papio Kinetic Sculpture Parade

Papio Kinetic Sculpture Parade

Apr 30 2022 - 8:30am
Human powered art sculptures take over Key West at the Papio Kinetic Sculpture Parade!Read more
key west songwriters festival

Key West Songwriters Festival

May 4 2022 - 7:00am to May 8 2022 - 11:30pm
The Key West Songwriters Festival -the largest festival of its kind in the world. 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 festival revolves around five...Read more

Pages