Waterfront Playhouse

Waterfront Playhouse Key West Announces Its 2026–2027 Season

The Waterfront Playhouse Key West returns with a vibrant 2026–2027 season that brings music, mystery, comedy, intimate storytelling, and Broadway-style emotion to one of the island’s most beloved cultural stages.

Located at Mallory Square, 407 Wall Street, the Waterfront Playhouse has long been part of the creative heartbeat of Old Town Key West. The intimate theater setting gives every production a close connection between audience and performer, making it a favorite for locals, seasonal residents, and visitors looking for a memorable night of live entertainment.

The new season, promoted as the Waterfront Playhouse’s 88th Season, offers a well-balanced lineup that moves from an electrifying rock concert experience to thoughtful solo performances, inventive holiday storytelling, fast-paced comedy, a soaring musical, and a classic suspense thriller.

A Season Built on Variety, Energy, and Connection

The 2026–2027 Waterfront Playhouse season opens in October with Hedwig and the Angry Inch, returning as an encore production just in time for the high-energy fall season in Key West. From there, the calendar moves through Spotlight Series performances, Mainstage productions, holiday theater, comedy, drama, music, and mystery.

This year’s lineup is especially strong because each production offers a different theatrical flavor. Audiences can expect glam-rock intensity, art-driven drama, holiday nostalgia, Tennessee Williams–inspired reflection, door-slamming farce, classic Hollywood character study, heartfelt musical storytelling, and an elegant murder mystery to close the season.

Tickets are available now through Waterfront Playhouse.

2026–2027 Waterfront Playhouse Season Lineup

Hedwig and the Angry Inch — Encore
October 15–23, 2026
A cult-classic rock musical filled with bold style, music, identity, humor, and high-voltage stage presence.

Destroying David — Spotlight Series
November 12–14, 2026
An intimate solo performance centered on art, beauty, loss, and the emotional power of Michelangelo’s David.

It’s a Wonderful Life: A Live Radio Play — Mainstage Series
December 2–17, 2026
A beloved holiday story reimagined as a live radio play, complete with nostalgic charm, ensemble storytelling, and theatrical sound.

Blanche and Beyond — Spotlight Series
January 7–9, 2027
A literary stage portrait inspired by the letters and life of Tennessee Williams, whose creative spirit remains deeply connected to Key West.

Unnecessary Farce — Mainstage Series
January 28–February 6, 2027
A fast-paced comedy packed with mistaken identity, physical humor, escalating chaos, and classic farce energy.

Call Me Elizabeth — Spotlight Series
February 11–13, 2027
An intimate theatrical portrait of Elizabeth Taylor, exploring fame, identity, love, and the public life behind a Hollywood legend.

Come From Away — Mainstage Series
March 4–20, 2027
A soaring musical about generosity, humanity, and connection, based on the remarkable true story of travelers welcomed in Newfoundland after September 11.

Dial M for Murder — Mainstage Series
April 8–17, 2027
A classic suspense thriller filled with jealousy, deception, murder, and sharp theatrical tension.

Live Theater Near Mallory Square

A night at the Waterfront Playhouse fits naturally into an Old Town Key West evening. The theater sits at Mallory Square, close to the Historic Seaport, Duval Street, and many of Key West’s best pre-show and post-show dining options.

For theater lovers, the Waterfront Playhouse 2026–2027 season offers a strong reason to plan ahead. With a lineup that stretches from October through April, the season gives audiences multiple chances to experience professional live theater in one of Key West’s most atmospheric performance spaces.