October 16 - 25, 2026 2026 Theme: Musical Icons & Iconic Musicals 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. […]
Sunday, November 22, 2026 Key West Theater, 512 Eaton Street The Buena Vista Orchestra comes to the Key West Theater, billed by its presenter as the world's foremost Cuban music repertory ensemble. The group works with a revolving lineup drawn from the original Buena Vista Social Club performances and from the bands of Celia Cruz, […]
Monday, January 18, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre America's premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo Wop Project takes today's biggest hits and "doowop-ifies" them — reimagining contemporary songs as though they'd been written and recorded in 1958. Familiar melodies arrive […]
Mile 0 Fest Key West January 26–30, 2027 · Truman Waterfront Amphitheater and venues across the island 10th Anniversary — Red Dirt, Americana & Texas Country Named the #1 music festival of 2025 by USA Today, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee […]
Thursday, February 11, 2027 Key West Theater, 512 Eaton Street Who's Bad brings its Michael Jackson tribute to the Key West Theater. The group has been at this since 2003 and has logged more than 2,500 performances — theaters, clubs, festivals, and House of Blues rooms across the U.S., plus tours through the U.K., China, […]
Saturday, March 13, 2027 Key West Theater, 512 Eaton Street Elton Dan & The Rocket Band bring their Elton John tribute to the Key West Theater. The band formed in 2015 and has since played more than 700 shows across 38 states, including a crowd of 18,000 at Kool Deadwood Nights in South Dakota in […]
Friday, March 19, 2027 Key West Theater, 512 Eaton Street The Linda Ronstadt Experience brings its tribute concert to the Key West Theater, fronted by American Idol alum Tristan McIntosh and backed by a full band. The show focuses on Ronstadt at the peak of her career, when she was the biggest-selling female recording artist […]
Sunday, April 11, 2027 Key West Theater, 512 Eaton Street 10,000 Maniacs play the Key West Theater. The band formed in Jamestown, New York in 1981 and has sold more than 10 million records, moving from the indie circuit to a central place in the alternative rock of the late 80s and early 90s. The […]
The Key West Songwriters Festival. 4/28/27 - 5/2/27 The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy […]
