• The Rat Pack: One More Time!

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    April 5th, 2025 RING–A-DING-DING! THE BEST RAT PACK SHOW RE-TURNS! Frank Sinatra, Dean Martin and Sammy Davis, Jr. return to stages all across America as the famous and infamous Rat Pack is resurrected by our three critically acclaimed entertainers. Relive those amazing nights with our international star performers. This show is the real deal. You’ll […]

  • STOMP!

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    May 23rd - 24th, 2025 Matchboxes, brooms, garbage cans, Zippo lighters, and more fill the stage with energizing beats at STOMP: the inventive and invigorating stage show that’s dance, music, and theatrical performance blended together in one electrifying rhythm.

  • The Rocky Horror Show

    Waterfront Playhouse 407 Wall Street, Key West, FL, United States

    Oct 15, 2025 - Oct 24, 2025 Celebrate the 50th Anniversary of “The Rocky Horror Picture Show” and the 5th Anniversary of this Fantasy Fest favorite at the Waterfront Playhouse! Richard O’Brien’s outrageous cult classic returns for an encore run filled with thrills, chills, and wild audience participation. Costumes encouraged!

  • Some Enchanted Evening

    Dec 4, 2025 - Dec 20, 2025 A stunning revue of Rodgers & Hammerstein’s most treasured songs, this elegant theatrical presentation brings five performers into a world of timeless music — from backstage intimacy to full-stage splendor. A heartfelt tribute to the golden age of Broadway.

  • Los Lobos

    It’s a matter of time. 50 years to be exact. And in that time Los Lobos have created an unprecedented body of work, a legacy of greatness. The numbers are staggering: 100+ gigs a year for five decades running, crossing millions of miles to rock millions of fans. And that’s just at the live shows. […]

    The Music of ABBA

    Tennessee Williams Theatre 5901 College Road, Key West, FL, United States

    A fun colorful family show, all the way from Sweden! With hits like Mamma Mia, Waterloo, Fernando and Dancing Queen, ABBA, Sweden’s biggest music export group ever, made their way into the hearts of people all around the world. We will give you the closest ABBA experience you’ll ever going to get with some of […]

    Mon January 26, 2026 The Phil Collins Experience The Phil Collins Experience is a dynamic multi-media production that pays tribute to the legendary music of Phil Collins and Genesis. Known as the most authentic Phil Collins tribute in the U.S., this show captivates audiences with its faithful recreation of the sights, sounds, and emotions of […]

    The Starters – By Laura Winters

    The Studios of Key West 533 Eaton St, Key West, FL, United States

    The Starters By Laura Winters Directed by Ashley Brooke Monroe Fri Jan 30 & Sat Jan 31, 8pm At 35 years old, Matt Shears is one of the oldest right tackles in the NFL. He and his wife, Emily, are planning for Matt’s retirement. But after Matt’s team goes to the Super Bowl, Matt is […]

  • The Patrons – By Nick Gandiello

    The Studios of Key West 533 Eaton St, Key West, FL, United States

    The Patrons By Nick Gandiello Directed by Aaron Rossini Fri Feb 13 & Sat Feb 14, 8pm In 1963, Head Librarian Mrs. Quarter is training Rhonda to serve the community amid budget cuts and a staff shortage. Unbeknownst to Quarter, Rhonda allows teenage patron Adam to check out a controversial book, which is soon voted […]

  • Once

    Waterfront Playhouse 407 Wall Street, Key West, FL, United States

    Mar 4, 2026 - Mar 21, 2026 Winner of eight Tony Awards, including Best Musical, Once tells the story of a disillusioned Dublin street musician whose music — and life — are transformed by an unexpected encounter with a woman who believes in him. Intimate, powerful, and deeply moving, this modern classic captures the magic […]