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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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.

Marathon

Marathon Community Theatre, Inc.

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

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

Tropic Cinema

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

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

Fringe Theater

Experience unique, community-driven theater with local talent in Key West!

Key West

Key West Theater

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

Islamorada

Tavernier Cinema 5

Tavernier Cinema 5 is a modern five-screen movie theater in Tavernier offering mainstream and 3D films with Dolby surround sound.

Key West

Comedy Key West

Experience top comedy shows and open mics in vibrant Key West! Laugh live now!

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.