Performing Arts
In the Florida Keys, stages are as lively as the sunsets. From community theaters and open-air concerts to symphonies, dance troupes, and quirky local productions, the islands love a show. On any given night you might catch a Broadway classic, a salsa band, or a cabaret that feels more like a family gathering than a performance. These listings point you to the theaters, music halls, and cultural spaces where Keys creativity takes the spotlight. Come early, stay late, and let the applause mix with the ocean breeze.
Jimmy Buffett
For millions around the world, the words Key West and Jimmy Buffett are nearly synonymous. He lived in the island city during some of his most productive years—developing the “tropical rock” style and laid-back persona that helped make him a world-renowned musical icon.
Tennessee Williams
Did you know that internationally renowned playwright Tennessee Williams lived in Key West for more than 30 years? During his time here, he completed "Summer and Smoke" and wrote "Night of the Iguana" among other works.
Famous Musicians Inspired by The Florida Keys
Bob Dylan loves Key West. In fact, the legendary singer-songwriter immortalizes it as “the enchanted land” and “land of light”. Others from the Keys include country superstars Kenny Chesney and Toby Keith.
President Harry S. Truman Little White House
“My grandfather once said that presidents shouldn’t have descendants,” revealed Clifton Truman Daniel, “because those descendants would spend the rest of their lives having people think they should live up to their ancestors.”
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Marathon
Marathon Community Theatre & Cinema
Marathon Community Theatre & Cinema is a nonprofit cultural hub in the Florida Keys offering live theater, films, dance, art, and educational programming.
Islamorada
Coral Shores High School Performing Arts Center
The Coral Shores Performing Arts Center in Tavernier hosts live theater, concerts, and community performances in the Upper Florida Keys.
Key West
Just a Few Friends Key West
Just a Few Friends Key West is a five-day island-wide Labor Day Weekend festival honoring Jimmy Buffett's legacy with free waterfront concerts, a second line parade, sunset sails, and live music events throughout Key West, September 3–7, 2026.
Key West
Waterfront Playhouse Theater
Waterfront Playhouse — community theatre & live performances in Key West, where intimate storytelling meets tropical charm.
Key West
Key West Outdoor Movies
Key West Outdoor Movies — free community movie nights under the stars at Fort East Martello, Key West.
Key West
Rams Head Presents
Rams Head Presents — live concerts & entertainment in Key West, where premium touring acts meet intimate island venues.
Key West
Red Barn Theatre
Red Barn Theatre — professional live theater in Key West, where big stories come alive in an intimate, historic space.
Marathon
Marathon Community Theatre, Inc.
Cinema in the Florida Keys, featuring musicals, comedies, and classic films.
Marathon
Marathon High School Performing Arts Center
The Marathon High School Performing Arts Center in Marathon, Florida is a vibrant local venue for student theater, musicals and community performances in the heart of the Florida Keys.
Key West
Shrimpboat Sound Studio
Shrimpboat Sound is the Key West recording studio Jimmy Buffett opened in 1986, set in an old ice house by the shrimp docks at the Historic Seaport. Buffett recorded much of his catalog here, and the studio hosted artists like George Strait, Alan Jackson, and Kenny Chesney before it closed after his death in 2023.
Key West
The Birdcage Cabaret
The Birdcage Cabaret — live drag & variety cabaret in Key West, where glitz, music & bold performances light up the night.
Key West
Tennessee Williams Museum
Tennessee Williams Museum — dedicated to the life and works of the famed playwright in Key West’s Little White House complex.
Key West
Randy Roberts LIVE!
Randy Roberts — performance magic & illusion shows in Key West, where spectacle meets island enchantment.
