Key West Events
Discover the best Key West events happening today, this weekend, and year-round!
Get the inside scoop on exciting festivals, including the world-famous Key West Fantasy Fest, the vibrant Key West Pride, and tasty celebrations like the Annual Key West Lobsterfest and Key Lime Festival. Enjoy daily favorites such as the iconic Sunset Celebration and live performances at the Key West Theater. Don’t miss thrilling annual highlights, from Hemingway Days to the Offshore Powerboat Racing World Championship. Explore our calendar now to find things to do in Key West and make unforgettable memories in paradise!
Key West Literary Seminar
January 7 - January 10, 2027
Pack Your Notebook: Key West's Most Poetic Weekend Awaits
Picture this: palm trees swaying, warm tropical breezes drifting down Duval Street, and some of the most celebrated poets alive today taking the stage just steps from the ocean. That's the Key West Literary Seminar, and the 2027 edition (January 7–10) is shaping up to be one for the books.
This year's theme? Poetry. And it's a full-circle...
Key West Half Marathon & 5K
January 16 - January 17, 2027
The 28th Annual Key West Half Marathon & Runfest is officially open for registration, bringing runners from around the globe to the island paradise from January 16–17, 2027. Voted one of USA Today’s Top 10 Half Marathons in the U.S. in 2023, this event offers multiple race options including the Half Marathon, 5K, 8K, 10K, plus fun challenges like the Big Pecker Challenge (5K, 10K, Half Maratho...
Southernmost Regatta
January 18 - January 22, 2027
Experience the Excitement of The Southernmost RegattaJanuary 18–22 | Key West, FloridaVisit: southernmostregatta.com
The Southernmost Regatta is a premier sailing event bringing together elite sailing teams from around the globe to compete in the stunning azure waters off Key West, Florida. Over five consecutive days of exhilarating races, vibrant sails, and unmatched sportsmanship, this regatta ...
Key West Food & Wine Festival
January 27 - January 31, 2027
18th Annual 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 at iconic island locations.
Over 20 unique events including waterfront tastings, winemaker/chef collaborations and local funky events that present an authentic taste of Key West, Florida
The place to be in January, ...
Florida Keys Seafood Festival
February 13 - February 14, 2027
Florida Keys Seafood Festival: Where Fresh Catch Meets Island Vibes
Mark those calendars, seafood lovers! The 20th Annual Florida Keys Seafood Festival is rolling into Truman Waterfront Park in Key West on February 13–14, 2027, and it's shaping up to be two unforgettable days of fresh-off-the-boat flavor, live music, and pure island magic. For just $10 admission, festivalgoers get full access to ...
Key West Songwriters Festival
April 28 - May 2, 2027
Experience the Magic of the 30th Annual Key West Songwriters Festival
Discover the stories behind the songs at the 30th Annual Key West Songwriters Festival, the world’s largest celebration of its kind. Presented by BMI and Rams Head Promotions, this iconic event takes place April 28 - May 2, 2026, in the charming and intimate settings of Key West, Florida.
Over the course of five unforgettable ...