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!
Sunset Celebration at Mallory Square
January 1 - December 31, 2025
Key West's world-famous Sunset Celebration takes place every evening at Mallory Square close to the foot of Duval Street. Featuring both renowned local and international artists and entertainers, the event invites visitors and locals alike to enjoy the sunset at water's edge. The event begins about two hours ahead of the sunset and ends soon after the sun sets. The performance takes place 365 days...
Offshore Powerboat Racing World Championships
November 2 - November 9, 2025
Key West Boat Races Extravaganza
The Key West Offshore Powerboat Racing World Championship is set to electrify the scene from November 2 – November 9, 2025 in Key West, FL. The event launches with a visual spectacle as the Parade Participants Lineup gathers on Sunday, November 2nd at 3:30 PM, followed by the First State Bank World's Fastest Boat Parade at 4:00 PM along Duval Street. This dynamic ...
30th Annual 5k Hog Trot
November 29, 2025 8:00 AM
The Hog Trot 5K returns to Key West on November 29, 2025, celebrating its 31st anniversary with a fun mix of fitness, community, and post-race revelry. The run kicks off at 8:00 AM from Hog’s Breath Saloon, 400 Front Street, with participants enjoying perks like a free Mich Ultra and a lively post-race party featuring Grey Goose Bloody Marys, Bombora Hog A-Laides, and High Noons at discounted pric...
Mac McAnally
December 4 - December 6, 2025
Mac McAnally Live at Key West Theater – December 4, 2025
A record-setting ten-time CMA Musician of the Year and a member of the Nashville Songwriters Hall of Fame, Mac McAnally is a true legend of American music. With inductions into the Mississippi and Alabama Music Halls of Fame, his career spans decades as a songwriter, singer, and instrumentalist. He has penned chart-topping hits for Alabama,...
Anthony Rodia : Laugh Till It Hurts Tour
December 11, 2025 8:00 PM
Anthony Rodia brings his hilarious Laugh Till It Hurts Tour to the charming Key West Theater in Key West, Florida. Known for his sharp observational humor and authentic storytelling, Rodia's performances resonate deeply with audiences through his witty portrayals of Italian-American culture, family traditions, and the comedic realities of everyday life.
Rodia first captivated audiences with viral...
Key West Triathlon
December 14, 2025 7:30 AM
The Key West Triathlon returns on Sunday, December 14, 2025, offering athletes a unique race experience in one of the most vibrant destinations in the U.S. Hosted at Higgs Memorial Beach, 1000 Atlantic Blvd, Key West, FL, the event is designed as the ultimate “tri-cation,” blending competition with relaxation in a lively island setting. Brought to life by Integrity Multisport™ and proudly sponsore...
New Year's Eve: Conch Shell Drop at Sloppy Joe's
December 31 - January 1, 2026
The arrival of 2026 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.
Inside Live music on stage noon-2:00...
Key West Literary Seminar
January 8 - January 11, 2026
The 43rd annual Key West Literary Seminar returns January 8–11, 2026, bringing readers and writers together for four days of world-class literary programming at the historic San Carlos Institute. Each year the event explores a unique theme, and in 2026 the focus is “Pay Attention! The Novel, or The Long Form in a Time of Short Attention.” The Seminar features presentations, readings, and conversat...
Jimmy Buffet's Coral Reefer Band
January 16, 2026 8:00 PM
Jimmy Buffett’s Coral Reefer Band will take the stage at the Coffee Butler Amphitheater on Friday, January 16, 2026, at 8:00 PM (doors open at 6:30 PM) for an all-ages show that keeps the late legend’s spirit alive. For over 50 years, the Coral Reefer Band helped Buffett craft the soundtrack of endless summers, salty breezes, and carefree living. After Buffett’s passing in 2023, the band—led by te...
Key West Half Marathon & 5K
January 17 - January 18, 2026
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 15–19, 2026. 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...