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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Key Largo

The Key Players

The Key Players — community theater productions in the Upper Keys, where local talent and lively storytelling bring stages to life.

Key West

San Carlos Institute

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

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

Tropic Cinema

Tropic Cinema — independent & art-house film venue in Key West, where cinematic magic meets community charm.

Key West

Key West Theater

The Key West Theater — performing arts & live events in Key West, where historic charm meets world-class entertainment.

Key West

The Birdcage Cabaret

The Birdcage Cabaret — live drag & variety cabaret in Key West, where glitz, music & bold performances light up the night.

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

Key West Outdoor Movies

Key West Outdoor Movies — free community movie nights under the stars at Fort East Martello, Key West.

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

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.

Marathon