• 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! […]

  • 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 […]

  • 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 […]

    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 […]

    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 […]

    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 […]

  • 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 […]

  • 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 […]

    Mom’s Best Friend – By Dan McCabe

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

    Mom’s Best Friend      By Dan McCabe Directed by Kate Whoriskey Fri Mar 20 & Sat Mar 21, 8pm June and her adult daughter, Christine, talk on the phone […]

    Taste of Key West

    Truman Waterfront Park Key West, FL, United States

    Annual Taste of Key West! Join us for Taste of Key West 2026 at Truman Waterfront on Monday, March 23rd! This open-air event promises an assortment of beverages and palate-pleasing […]