A Year of Magic, Music, Mystery, and Meaning Awaits in 2025–2026

Key West, FL — The Waterfront Playhouse is thrilled to unveil its exciting 87th Season, packed with beloved classics, thrilling new voices, and unforgettable theatrical experiences. This season features a bold lineup of Mainstage productions and Spotlight Series performances, each designed to entertain, engage, and inspire. From cult rock musicals and intimate dramas to magical solo shows and Tony Award-winning sensations, there’s something for everyone on our stage.

ENCORE PRESENTATION

“The Rocky Horror Show”

October 15–24 at 7:30 PM

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!

SPOTLIGHT SERIES 1

“Fooling Buddha”

November 13–15 at 7:30 PM

A witty and magical coming-of-age story about the first “American Buddhist” kid on the block in the 1970s. Combining masterful storytelling with sleight-of-hand and spiritual insight, this enchanting solo performance is created by and stars David Kovac a favorite performer at Hollywood’s Magic Castle.

MAINSTAGE 1

“Some Enchanted Evening”

December 4–20 at 7:30 PM

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.

SPOTLIGHT SERIES 2

“What the Constitution Means to Me”

January 1–3 at 7:30 PM

Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this critically acclaimed and deeply personal play, she resurrects her teenage self to examine how our founding document has shaped generations of American women. “Not just the best play to open on Broadway this season, but also the most important.” – The New York Times

SPOTLIGHT SERIES 3

“Tuesdays With Morrie”

January 15–17 at 7:30 PM

A moving adaptation of Mitch Albom’s bestselling memoir, this play follows the touching reunion between a busy journalist and his former professor, Morrie Schwartz, who is facing ALS with heart, humor, and wisdom. An unforgettable drama that celebrates what truly matters.

MAINSTAGE 2

“Almost, Maine”

January 29–February 14 at 7:30 PM

This whimsical and heartfelt series of vignettes explores the joys and sorrows of love in a mythical town in northern Maine. The New York Daily News wrote: “Almost, Maine’s charm is real. It packs wit, earns its laughs, and, like love, surprises you.”

MAINSTAGE 3

“Once”

March 4–21 at 8:00 PM

Winner of eight Tony Awards, including Best Musical, Once tells the story of a disillusioned Dublin street musician whose music — and life — are transformed by an unexpected encounter with a woman who believes in him. Intimate, powerful, and deeply moving, this modern classic captures the magic of connection.

MAINSTAGE 4

“Accomplice”

April 9–18 at 8:00 PM

A deliciously twisted comic thriller by Tony Award winner Rupert Holmes. Winner of the Edgar Award for Best Mystery Play, Accomplice keeps audiences laughing and guessing with its brilliant mix of deception, misdirection, and theatrical surprises. You’ll be sworn to secrecy!

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Season Subscriptions Coming Soon


Don’t miss a moment of this incredible season. Subscription packages will be available soon, offering the best seats at the best value. Be part of Key West’s premier theatrical tradition — and help us celebrate 87 years of extraordinary storytelling at the Waterfront Playhouse.

For tickets and more information, visit www.waterfrontplayhouse.org or call 305-294-5015.