Waterfront Playhouse

Waterfront Playhouse Key West — 2025–2026 Live Theater Season

The Waterfront Playhouse Key West returns with a compelling 2025–2026 theater season that continues its legacy as one of Old Town’s most respected cultural stages. Located just steps from the Historic Seaport at 407 Wall Street, this intimate venue delivers an expertly curated lineup of Mainstage productions and Spotlight Series performances, blending acclaimed musicals, contemporary drama, and inventive storytelling in a setting designed for close connection between audience and performers.

The season opens with the high-energy return of Rocky Horror Show (Encore) from October 15 – October 24, 2025, a long-standing Fantasy Fest favorite known for its interactive fun and cult following. Throughout the fall and winter, audiences can experience intimate Spotlight productions including Fooling Buddha (November 13 – November 15, 2025), What the Constitution Means to Me (January 1 – January 4, 2026), and the moving adaptation Tuesdays With Morrie (January 15 – January 18, 2026).

Mainstage offerings anchor the season with memorable productions such as Some Enchanted Evening (December 4 – December 20, 2025), a celebration of classic Broadway songwriting, followed by the beloved ensemble favorite Almost, Maine running January 29 – February 14, 2026. Spring brings the emotionally rich, Tony Award–winning musical Once (March 4 – March 21, 2026), before the season concludes with Accomplice (April 9 – April 18, 2026), a clever, audience-engaging mystery that blends humor with intrigue.

With its Old Town location, live theater in Key West at the Waterfront Playhouse pairs naturally with an evening of exceptional dining. Pre-show and post-curtain plans are easily elevated with nearby culinary options, making each performance part of a complete night out in historic Key West.

Venue Information
Waterfront Playhouse
Address: 407 Wall St, Key West, FL 33040
Phone: (305) 294-5015