2025/26 Season at Tennessee Williams Theatre

Tennessee Williams Theatre in Key West – 2025/26 Shows & Events

Discover the 2025/26 Season at Tennessee Williams Theatre

The Tennessee Williams Theatre in Key West continues its tradition as a cultural centerpiece, bringing world-class performances to the island throughout the 2025/26 season. With three distinctive stages—the Mainstage Theater, Cabaret Theater, and Blackbox Theater—the venue presents an eclectic mix of Broadway productions, comedy, classical music, dance, and special one-night engagements. Each show is carefully curated to highlight both international stars and beloved local talent, making it one of the most dynamic entertainment destinations in the Florida Keys.

2025/26 Season Highlights

This season delivers an exciting calendar of performances, offering something for every taste:

• The Magnificent Circus Mystery – October 28, 6:30 PM

• An Evening with David Sedaris – November 1, 7:30 PM

• An Evening in Conversation with Kenny Chesney – November 10, 7:30 PM (Sold Out)

• Vicki Roush & Laurie Breakwell – November 13, 7:30 PM

• Ann Hampton Callaway – November 17, 7:30 PM

• Cello Stories: A Life under Broadway – December 5, 7:30 PM

• Keys Choral Arts: Annual Holiday Concert – December 14, 4:00 PM

• Direct From Sweden: The Music of ABBA – January 21, 7:30 PM

• Vienna Boys’ Choir – February 5, 7:30 PM

• New York Philharmonic String Quartet – February 10, 7:30 PM

• Pilobolus Dance Company – February 13, 7:30 PM

• Neil Berg’s 50 Years of Rock n Roll – February 27, 7:30 PM

• Illusionist Rick Thomas – March 3, 7:30 PM

• The Doo Wop Project – March 11, 7:30 PM

• Jazz at Lincoln Center: Great American Crooners – March 24, 7:30 PM

• Houston Ballet II – March 30, 7:30 PM

• Anne McKee Artists Fund Performance featuring Belle Jampol – April 4, 7:30 PM

• Puppy Pals Live! – April 6, 6:30 PM

• Endless Summer Fundraiser with Howard Livingston & Friends – April 11, 7:30 PM

• Jillian Todd – Joni Mitchell Tribute – April 15, 7:30 PM

• One Night of Queen – May 3, 7:30 PM

Additionally, the Impromptu Classical Concert Series showcases renowned musicians including Ulysses Quartet, Yevgeny Kutik, Dorian Wind Quintet, Horszowski Trio, George Li, and the Carr-Petrova Duo.

Box Office & Ticket Information

Tickets for the 2025/26 Tennessee Williams Theatre season are available online and at the Box Office. Patrons can save up to 15% with flexible season packages that include priority seating and early access. Due to high demand, many shows—such as Kenny Chesney’s sold-out evening—encourage advance booking.

About the Tennessee Williams Theatre

Named in honor of the legendary playwright who once called Key West home, the theatre has been a hub for cultural enrichment for more than 40 years. Its three stages offer distinct experiences: the Mainstage Theater for major productions, the Cabaret Theater for intimate performances, and the Blackbox Theater for innovative, community-focused events.

Supporting the Arts in Key West

As a nonprofit institution, the Tennessee Williams Theatre depends on the support of patrons and donors to sustain its programming and community initiatives. Contributions help fund education, outreach, and a diverse calendar of events, while donors enjoy exclusive benefits and early ticket access.

Travel Tip: Pair a night at the Tennessee Williams Theatre with Dinner on Duval Street or a Key West Sunset Sail to create an unforgettable island evening.