Man in Renaissance costume reaching for a woman above a brick wall.

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 Buffet in a cap waves at a large, cheerful crowd at an outdoor event.

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.

Outdoor gathering by the sea at sunset, people dancing and cheering near a stage.

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.

Clifton Truman Daniel portraying grandfather Harry Truman

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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Key West

Frank Everhart Comedy Magic Shows

Frank Everhart — comedy-magic shows & entertainment by a master illusionist in Key West.

Key West

Tennessee Williams Theatre

Tennessee Williams Theater — immersive theater & experiential performances in Key West, where storytelling becomes adventure.

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

Rams Head Presents

Rams Head Presents — live concerts & entertainment in Key West, where premium touring acts meet intimate island venues.

Key West

The Key West Amphitheater

The Key West Amphitheater — live music & concert venue in Key West, where island vibes meet high-energy performances.

Key West

San Carlos Institute

San Carlos Institute — Cuban heritage museum & cultural center in Key West, where history, art, and independence converge.

Key West

Williams Hall

Williams Hall — restored historic community venue hosting concerts, cultural events, culinary experiences and inter-generational programs in Key West.

Marathon

Marathon Community Theatre, Inc.

Cinema in the Florida Keys, featuring musicals, comedies, and classic films.

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.