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.

Musicians performing onstage at sunset, with vibrant red lighting.

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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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

Rams Head Presents

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

The Lower Keys

Island Groove Dance Studio

Ignite your passion with expert dance training in a supportive, vibrant community!

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.

Marathon

Marathon Community Theatre, Inc.

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

Key West

801 Bourbon Bar

801 Bourbon Bar is Key West's legendary LGBTQ nightclub at 801 Duval Street — home to the world-famous 801 Girls drag show, daily specialty cocktails, karaoke, bingo, and nonstop fun from noon to 4 AM every single day.

Key West

Key West International Dance Company

Experience vibrant cultural dance and bold artistry with Key West International Dance Company!

Key West

Red Barn Theatre

Red Barn Theatre — professional live theater in Key West, where big stories come alive in an intimate, historic space.

Key West

San Carlos Institute

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

Key West

St. Paul's Episcopal Church Key West

Founded in 1832 and the oldest congregation in Florida south of St. Augustine, St. Paul's Episcopal Church is one of Key West's most treasured historic landmarks, offering weekly worship, an annual concert series, and five on-grounds wedding and event venues at 401 Duval Street — all while undergoing a breathtaking historic restoration for its 200th anniversary in 2032.