Waterfront Playhouse Presents: Updated 2025/2026 Season
When: December 12 - April 18, 2026
Where: Waterfront Playhouse, 407 Wall St, Key West, FL 33040
Waterfront Playhouse — 2025–2026 Season
407 Wall St, Key West, FL 33040
(305) 294-5015
🎭 Welcome to the 2025–2026 Season!
Get ready to experience one of Key West’s most celebrated cultural traditions! The Waterfront Playhouse returns with a spectacular lineup of powerful dramas, classic musicals, intimate spotlight productions, and special seasonal presentations. Whether you’re a longtime theater lover or discovering live performance in the Keys for the first time, this season brings compelling storytelling, world-class talent, and unforgettable evenings in the midst of Mallory Square.
From the outrageous fun of Rocky Horror Show to evocative tales of love, mystery, and community, each production is staged in the Playhouse’s intimate setting — the perfect backdrop for a night that moves both heart and imagination.
Make an evening of it: after your show, be sure to continue the experience with a night of exceptional cuisine in Key West. Explore our guide to fine dining for extraordinary meals before or after curtain call 👉 Key West Fine Dining — from oceanfront seafood to elegant Old Town restaurants, there’s a perfect dinner waiting. Key West Casual Dining
🎟️ 2025–2026 Season at a Glance
| Show Title | Series | Dates |
|---|---|---|
| Rocky Horror Show (Encore) | Mainstage | Oct 15 – Oct 24, 2025 |
| Fooling Buddha | Spotlight Series | Nov 13 – Nov 15, 2025 |
| Some Enchanted Evening | Mainstage | Dec 4 – Dec 20, 2025 |
| What the Constitution Means to Me | Spotlight Series | Jan 1 – Jan 4, 2026 |
| Tuesdays With Morrie | Spotlight Series | Jan 15 – Jan 18, 2026 |
| Almost, Maine | Mainstage | Jan 29 – Feb 14, 2026 |
| Once | Mainstage | Mar 4 – Mar 21, 2026 |
| Accomplice | Mainstage | Apr 9 – Apr 18, 2026 |
🎭 Season Highlights
Rocky Horror Show (Encore)
Ongoing Fantasy Fest favorite — a wild, interactive musical event perfect for fans of cult classics.
Fooling Buddha (Spotlight Series)
An inventive solo performance weaving storytelling, humor, and magic.
Some Enchanted Evening (Mainstage)
A musical revue featuring timeless songs that celebrate the golden age of Broadway.
What the Constitution Means to Me (Spotlight)
A thought-provoking contemporary play about democracy and personal history.
Tuesdays With Morrie (Spotlight)
A heartfelt stage adaptation of the beloved memoir about life lessons and connection.
Almost, Maine (Mainstage)
A tender ensemble piece about love and chance encounters in a small town.
Once (Mainstage)
The Tony-winning musical that blends music and emotion in a story of connection and hope.
Accomplice (Mainstage)
A clever, humorous whodunit that invites audience engagement.
You might like these Events
Key West Holiday Parade 2025
Key West Holiday Parade 2025 Lights Up Old Town with Holiday Spirit Key West Holiday Parade – Saturday, December 6, 2025Time: 7:00 PM – 10:00 PMLocation: Through the streets of Old Town, Key West, FL...
Mac McAnally (3rd Show Added!)
Live at Key West Theater: Mac McAnally in Concert 10-time CMA Musician of the Year Mac McAnally takes the stage at Key West Theater for a one-night performance that blends world-class songwriting, le...
Femmes of Rock
FEMMES OF ROCK at Key West Theater: Electrifying Strings and Rock Legends Live FEMMES OF ROCK brings its internationally acclaimed, high-octane string rock experience to the Key West Theater for a ni...
BTE-1 • Two Hour Boat Charter
Best Time Ever Boat Charters, LLC.
Experience a private boat charter in the Florida Keys. Spacious, stylish, fast. Perfect for group outings.
Book now!
