Discover the best festivals and events in Key West!
From captivating theater performances and comedy shows to exhilarating fishing tournaments and literary seminars, our curated event listings offer unforgettable experiences year-round. Plan your perfect Key West getaway and immerse yourself in the vibrant local culture, entertainment, and island charm.
The Expanding Man: An Original Tribute To Steely Dan & Beyond
Experience The Expanding Man at Key West Theater On January 14, 2026, Key West Theater at 512 Eaton St. hosts The Expanding Man: An Original Tribute to Steely Dan & Beyond, a mesmerizing performa...
Jimmy Buffet’s Coral Reefer Band
The Coral Reefer Band Live at Coffee Butler Amphitheater – January 16, 2026 A Night of Jimmy Buffett’s Timeless Music in Key West On Friday, January 16, 2026, the Coffee Butler Amphitheater at Truma...
Key West 28th Annual Half Marathon & Runfest
Key West Half Marathon & RunFest 2026 | Historic Seaport Experience one of the nation’s most celebrated winter race weekends at the 28th Annual Key West Half Marathon & RunFest, returning Jan...
The Brit Pack: The Ultimate British Music Experience
The Brit Pack Live at Key West Theater: A British Rock Revival Experience the ultimate British Invasion tribute when The Brit Pack takes the stage at Key West Theater. This dynamic ensemble, formed b...
Southernmost Regatta 2026
Southernmost Regatta 2026 — Key West Sailing Competition & Island Culture The Southernmost Regatta 2026 returns to Key West, Florida from January 19–23, 2026, bringing together elite sailors and ...
Key West Food & Wine Festival
Key West Food & Wine Festival 2026 — Culinary Masters & Island Pairings Experience the Art of Taste at the Key West Food & Wine Festival 2026 From January 21–26, 2026, Key West transform...
Rumours ATL- A Fleetwood Mac Tribute
Key West Theater Presents Rumours ATL - A Fleetwood Mac Tribute On January 21, 2026, music enthusiasts will gather at the Key West Theater for an unforgettable evening with Rumours ATL: A Fleetwood M...
Mile 0 Fest
Mile 0 Fest 2026 at Coffee Butler Amphitheater Mile 0 Fest Key West 2026 returns Tuesday–Saturday, January 27–31, 2026, for five days of Red Dirt and Americana set against the island’s most scenic ba...
Gabriel Rutledge: Don't Read the Comments Tour
Gabriel Rutledge Live at Key West Theater – February 15, 2026 On Sunday, February 15, 2026, nationally acclaimed comedian Gabriel Rutledge takes the stage at the Key West Theater, 512 Eaton Street, b...
