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!
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...
Southernmost Regatta
January 19 - January 23, 2026
Experience the Excitement of The Southernmost RegattaJanuary 19–23 | 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 ...
Kelly McGillis Classic
January 20 - January 26, 2026
Experience the Thrill of Female Athleticism at the 34th Annual Kelly McGillis Classic!
Event Overview: The Kelly McGillis Classic International Women’s & Girls’ Flag Football Championship, set to take place from January 20–26, 2026, in the vibrant city of Key West, is a one-of-a-kind global celebration of female athleticism and camaraderie. Attracting over 30 teams of women and girls from acr...
Mile 0 Fest
January 27 - January 31, 2026
Experience Five Unforgettable Nights of Music in ParadiseJanuary 27th - January 31st, 2026
Mile 0 Fest Key West invites music enthusiasts to indulge in a spectacular boutique festival where the rhythms of Red Dirt and Americana music meet the serene beauty of Key West. This premier annual event combines stellar performances by iconic and emerging artists with the island’s relaxed, vibrant atmosph...
Key West Food & Wine Festival
January 28 - February 1, 2026
17th 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 14 - February 15, 2026
Experience Fresh Local Seafood and Live Music at the Florida Keys Seafood Festival
The Florida Keys Seafood Festival is a premier two-day celebration held at Key West’s Truman Waterfront Park, where the local fishing community showcases the freshest catch in the Keys. This annual event, taking place on February 14th and 15th, offers a vibrant mix of culinary delights, live music, family-friendly ...
Key West Art & Craft Festival
February 21 - February 22, 2026
Celebrate the 60th Key West Art & Craft Festival at Truman Waterfront Park
Mark your calendars for February 21-22, 2026, as the Key West Art & Craft Festival returns for its 60th anniversary in the picturesque setting of Truman Waterfront Park in Old Town Key West. This highly anticipated juried event, hosted by the Key West Art Center—Key West’s oldest art gallery and a proud nonprofit c...
Changes In Latitude
March 3, 2026 8:00 PM
Experience the ultimate Jimmy Buffett tribute at the Key West Theater on Tuesday, March 3, 2026, as Changes In Latitudes brings their nationally acclaimed, sun-soaked show to paradise. Renowned as the premier Jimmy Buffett tribute band, Changes In Latitudes delivers an amazingly authentic reproduction of Buffett’s legendary performances, featuring all your favorites like "Margaritaville," "Cheeseb...
Conch Shell Blowing Contest
March 7, 2026 10:30 AM
Experience the Timeless Key West Conch Shell Blowing Contest
A celebrated tradition in Key West, the Conch Shell Blowing Contest has enchanted audiences for over 60 years. Held at the historic Oldest House Museum and Garden, this unique event brings together participants of every age—from toddlers to seniors—challenged to create musical magic with fluted conch shells. The spirited competition fea...