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Key West Events
Key West events happen all year round. It’s hard to plan a visit to Key West and not have some event happening. I have tried to compile a list of events by the month as I know them so you can plan a visit to Key West around them.
Some events come and go but the big ones have become tradition.
Check out our Key West events calendar. A month by month schedule of events calendar guide to the happenings of our island city. I keep it up and current with what I know is happening for the year here in Key West.
If there is a play, a festival, a concert, or anything else happening in Key West you can find out here! – Just Click the button below.
Key West Events In August 2025
Key West Tropical Heat – August 13, 2025 – August 17, 2025 – Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s events range from all-male theme parties, pool parties and entertainment showcases at the island’s LGBTQ venues. Attendees can also enjoy activities ranging from eco-tours to museum explorations.
Rum Fest Key West – August 13, 2025 – August 17, 2025 – Key West is famous for tropical heat, mouth watering seafood and some of the best rum you can get your hands on, among many other things. Rum Fest Key West showcases the best rum from around the world. Experiences include sunset sails, sandbar trips, rum strolls, food and cigar events featuring rum, two Jesse Rice concerts and a third concert with Cliff Cody and Sharese during the annual rum cake competition at Key West Theater, a rum grand tasting and more.
Just a Few Friends – August 29 – September 2, 2025 – Key West’s 2nd annual festival begins 4 p.m. Aug. 29 and ends on September 2. Join us in honoring Jimmy Buffet’s legacy with a tribute concert, vote in a cheeseburger battle, and a sunset boat ride.
5k Special – August 30, 2025 – Mile 0 Events & Irish Kevin’s presents the Parrots and Margaritas 5k on Aug. 30 at 8:00 a.m. Join and be part of this 5k run and enjoy a post-race party at Irish Kevin’s. Tickets are $51.99. 211 Duval St. Key West.
Key West Brewfest – August 30, 2025 – Southernmost Beach Resort hosts Key West Brewfest Aug. 30, 3:00-8:00 p.m. Event includes beer dinner pairings, pool parties, and tastings. Tickets start at $45. 1319 Duval Street, Key West.
BBQ Rib Battle – August 31, 2025 – The Key West Chamber of Commerce presents the 6th annual BBQ Rib Battle Aug. 31, 11:30 a.m.-4:00 p.m. Grill masters show off their skills while their fans cheer them on. Homemade BBQ, sides, music, and drinks. 124 Ann Street, Key West. 305-294-2587.
Key West Events In September 2025
Womenfest Key West – September 3, 2025- September 7, 2025 – The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling, sunset cruises to live entertainment, an art workshop and much more.
5th Annual Corn Hole Tournament – September 4, 2025 – Key West’s annual Corn Hole Tournament is back on Sept. 4 at 3:00 p.m. Bring a teammate or two to join for fun games, drinks and friends. Tickets are $28.24/ TEAM. American Legion Post 168 803 Emma Street. 800-535-7797.
Key West Events In October 2025
Southernmost Half Marathon Special Event – October 12, 2025 – 6:00 AM - 10:00 AM. This is a rolling street closure. The race begins and ends at Higgs Beach. The route consists of Higgs Beach to Fort Street, through Truman Waterfront Park, up Front Street to Mallory Square then reversing back to Higgs Beach.
Fantasy Fest – October 17, 2025 – 26, 2025 – Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! The winning theme for Key West Fantasy Fest 2025, which is scheduled for Oct. 17-26, is “Bedtime Stories & Magical Monsters.” Ellen LaMoia of Key West, Fla., has scored Fantasy Fest Parade Grand Stand seats where she will enjoy the 2025 spectacle seated among the parade’s judges and organizers for her contribution to the theme.
Fantasy Fest Zombie Bike Ride – October 19, 2025 – The annual Rock n’ Roll costumed Zombie bike ride returns for another wild run on Sunday, Oct. 19. The Zombieland pre-ride party takes place at Fort East Martello, 3501 S. Roosevelt, from 2 to 6 p.m. with face and body painters, food vendors and a full bar. The ride, with thousands of costumed zombies, rolls out at 6 p.m. going down A-1-A then through downtown. The ride ends with a dance party at the Coffee Butler Amphitheater at Truman Waterfront Park presented by Rams Head. Register online in advance for $10.
Fantasy Fest Masquerade March (aka The Local’s Parade) – October 24, 2025 – Join the hugely popular Fantasy Fest tradition known as the locals’ parade that highlights costumes, creativity and community. The Captain Morgan Masquerade March is a grown-up moving cocktail and dance party that begins at 5:30 p.m. at Truman Ave. and Frances St. The route winds its way north to Fleming St., stopping at participating guest houses that hand out complimentary beverages.
Fantasy Fest Parade – October 25, 2025 – Join 70,000 exuberant partygoers as the Key West Fantasy Fest parade rolls down Duval Street featuring glittering floats, spectacular costumes and dazzling dancing groups, some dressed and decorated to illuminate this year’s theme of “Bedtime Stories & Magical Monsters.” It doesn’t get any wilder than this! Parade steps off at 7 PM; Free to attend for spectators
Fantasy Fest
Quite possibly the mother of all Key West events. A week or so long festival of anything a person can imagine and more. Fantasy fest has a theme for every day of the festival and parties and get togethers. Things like Toga Night and Tu Tu Tuesday.
Pre leading Fantasy Fest there is Goombay Festival full of food and music getting us all ready for Fantasy Fest.
Key West Events In November 2025
Key West Race World Offshore November 2-9. Watch as this legendary offshore power boat race draws some of the fastest boats in the world to compete for the world championship right before your eyes. Meet the drivers, see the boats. See the full schedule here.. Race Week Schedule
2025 Key West Film Festival – November 12 – 16. The Key West Film Festival—where passion meets paradise—is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops. Film screening venues include San Carlos Institute, The Studios of Key West and Williams Hall.
Key West Events In December 2025
Christmas Lights In The Tropics – December 18th end of the month. Who doesn’t like Christmas lights? Roll the dice on climate for feeling like Christmas we can sure there will be not be snow. There are tours self guided and guided to see the houses in Key West that participate in their own way to celebrate Christmas in Key West.
Key West Christmas Parade- December 6th 2025. Come see the southernmost Christmas spectacular. Parade route goes through Key West and right down Duval Street. A great time for all ages and lots of candy being tossed from parade floats. Santa Will be making an appearance. (probably wearing something tropical).
Key West Lighted Boat Parade – Sometime 3rd week TBA – Local businesses and residents put up the lights for this really fun parade on the water in the harbor of Key West. Get in the spirit and watch from land near the Schooner Wharf or Hire a Lighted Boat Parade Charter And see all the incredible boats up close and personal.
Click Here For The Best – Key West Sandbar Trips
Check out which cruise ship will be in Key West and when by looking at my Key West cruise ship schedule. As soon as the cruise lines release the dates I will have them here. Key West has been a cruise port since the early 90s. They bring a number of tourists here nearly every day. Ships from all the major cruises come to Key West.