Theaters & Performance

The Waterfront Playhouse

Florida Keys · Key West $$
Live Performances Waterfront

About

The Waterfront Playhouse calls itself the oldest continually running theater group in Florida, and its 2025 to 2026 season is its 86th. The Main Stage series leans toward well known titles such as Wait Until Dark, La Cage Aux Folles, and Singin’ in the Rain, while the On The Edge series takes on edgier shows like The Rocky Horror Show. Casts include professional actors from around the country.

The house is small, so every seat feels close to the stage. Book ahead in winter and spring, when shows often sell out. It sits right at Mallory Square, so plan dinner nearby and catch the sunset celebration before an evening curtain. Ask about group rates and gift certificates through the box office.

Good to know

Two series
Main Stage shows are crowd pleasers, while On The Edge productions are more daring.
Sunset first
The theater is at Mallory Square, so you can watch the sunset celebration before an evening show.
Groups
Group discounts and gift certificates are available through the box office.
Tickets are moving fast for the first show in our Spotlight Series! Destroying David takes the audience on thought-provoDESTROYING DAVID 💪 Nov 12 - Nov 14, 2026 The Spotlight Series begins with the Florida premiere of “Destroying David”, an🌟 MEET THE CAST! 🌟 Destroying David - Jessica Miano Kruel Jessica is a bicoastal actor who flees the harsh winters of LALunch plans?! 🍕 Thank you to White Street Pizza for making the Waterfront Playhouse their monthy fundraiser recipient. GPizza For Purpose! 🍕 Thank you to our friends at whitestreetpizza for their fundraising efforts! Stop in EVERY WEDNESDAYMEET THE DIRECTOR! 🎭 Hedwig and The Angry Inch JEREMY ZOMA 👏 Jeremyis so excited to be back this season at the Waterfron