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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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
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 Impromptu Classical Concerts
Key West Impromptu — chamber music concert series in Key West, where world-class classical performance meets community spirit.
Key West
Comedy Key West
Experience top comedy shows and open mics in vibrant Key West! Laugh live now!
Key West
Rams Head Presents
Rams Head Presents — live concerts & entertainment in Key West, where premium touring acts meet intimate island venues.
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
Williams Hall
Williams Hall — restored historic community venue hosting concerts, cultural events, culinary experiences and inter-generational programs in Key West.
Key West
Waterfront Playhouse Theater
Waterfront Playhouse — community theatre & live performances in Key West, where intimate storytelling meets tropical charm.
Key West
Key West Burlesque
KW Burlesque — live burlesque & cabaret performances in Key West, where daring glamour meets island nightlife.
Key West
San Carlos Institute
San Carlos Institute — Cuban heritage museum & cultural center in Key West, where history, art, and independence converge.
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
Shrimp Boat Sound Studio
Shrimpboat Sound Studio — historic recording studio in Key West, where legends like Jimmy Buffett made music in a humble, iconic space.
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
Frank Everhart Comedy Magic Shows
Frank Everhart — comedy-magic shows & entertainment by a master illusionist in Key West.
