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!
Rum Fest Key West
August 10 - August 16, 2026
Rum Fest Key West returns for its highly anticipated Second Annual Key West Rum Fest, celebrating the island's legendary tropical vibes, mouthwatering seafood, and exceptional rums from around the globe. Scheduled from August 10 to August 16, 2026, this vibrant event combines premium rum tastings, captivating live performances, and unforgettable culinary experiences, all benefiting the local nonpr...
Just A Few Friends
September 3 - September 7, 2026
Just A Few Friends: Key West's Ultimate Jimmy Buffett Celebration Awaits
Picture this: five sun-soaked days in the heart of Key West, where the salt air mingles with steel drums, margaritas flow freely, and Jimmy Buffett's legacy comes alive on every corner. Mark those calendars for September 3 – September 7, 2026, because the Just A Few Friends festival is rolling out the welcome mat for Parroth...
Fantasy Fest® 2026
October 16 - October 25, 2026
Key West Fantasy Fest 2026: The Ultimate 10-Day Caribbean Celebration
Fantasy Fest returns to Key West for an extraordinary celebration from October 16-25, 2026, transforming the island paradise into a vibrant playground of creativity and imagination. This world-renowned festival, celebrating its legacy since 1979, invites adults from around the globe to experience ten unforgettable days of costu...
Fantasy Fest 5K Run/Walk
October 19, 2026 6:00 PM
Run Wild in Paradise: The Fantasy Fest 5K is the Most Magical Mile You'll Ever Take
Ready to lace up for the wildest Monday night of your life? Welcome to the Fantasy Fest 5K Run/Walk—where fairy tales meet finish lines and the streets of Key West come alive with whimsy, costumes, and cocktails. More than just a race, this Monday night party kicks off Fantasy Fest 2025 in true Key West style. Sta...
Offshore Powerboat Racing World Championships
November 1 - November 8, 2026
Key West Boat Races Extravaganza
The Key West Offshore Powerboat Racing World Championship is set to electrify the scene from November 1 – November 8, 2026 in Key West, FL. The event launches with a visual spectacle as the Parade Participants Lineup gathers on Sunday, November 1nd at 3:30 PM, followed by the First State Bank World's Fastest Boat Parade at 4:00 PM along Duval Street. This dynamic ...
32nd Annual 5k Hog Trot
November 28, 2026 8:00 AM
The Hog Trot 5K returns to Key West on November 28, 2026, celebrating its 32nd 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...
Key West Triathlon
December 13, 2026 7:30 AM
The Key West Triathlon returns on Sunday, December 13, 2026, 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, 2027
The arrival of 2027 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 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...