• Free Fallin, The Tom Petty Concert Experience!

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

    March 29th, 2025 Get ready for an epic live show with Free Fallin, The Tom Petty Concert Experience! Enjoy this vibrant musical journey remembering the one and only, Tom Petty!  Watch as these highly skilled musicians perform his iconic hits. Perfect for those who’ve grown up to classics like ‘American Girl’, ‘Free Fallin’ and ‘Mary […]

  • Wait Until Dark

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

    Wait Until Dark The final show of the season is, according to the New York Post, “A first rate shocker… The suspense drama we’ve long awaited eagerly… A classic”. Written in 1966 by Frederick Knott and then adapted by Jeffrey Hatcher in 2013, this is the story of a blind woman in Greenwich Village in […]

    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 […]