Winter Park Playhouse
Dinner & A Show
1 Days | Year-Round
Starting At $Flexible Pricing
Enjoy dinner and a show in Winter Park, FL. The Winter Park Playhouse is known for outstanding entertainment, welcoming atmosphere and exceptional service. The intimacy of the 123-seat theatre engages patrons in a unique up-close-and-personal theatrical experience.
|Current Show Schedule:
YankeeTrailsGroups by US Tours Flexible Pricing:
- Customizable Comps
- Net Rates
- Luxury or First Class Hotels & Meals
- Motorcoach Transportation & Professional Tour Managers are available
Whatever you want, YankeeTrailsGroups by US Tours will be happy to structure tour prices to match your needs. Just let us know!
Travel today to Winter Park, FL for an evening of theatre. First start with dinner at a local restaurant followed by a show at the Winter Park Playhouse. Located blocks away from beautiful downtown Winter Park and minutes from downtown Orlando, The Playhouse is known for its outstanding entertainment, welcoming atmosphere and exceptional service. The intimacy of the 123-seat theatre engages patrons in a unique up-close-and-personal theatrical experience.
Current Show Schedule
- Nov 10 to Dec 16 – A Swingin’ Christmas: The Holiday Music of Tony Bennett
- Jan 19 to Feb 17 – Breaking Up is Hard to Do
- March 15 to April 20 – Five Guys Named Moe
- May 10 to June 9 – George M. Cohan Tonight!
A Swingin’ Christmas: The Holiday Music of Tony Bennett Nov 10 to Dec 16
Ring in the holidays with this unforgettable evening of quintessential Tony Bennett songs! Featuring eighteen classic holiday tunes plus the standards that made Bennett famous, like “I Wanna Be Around,” “The Good Life,” “Rags to Riches” and, of course, Tony’s signature “I Left My Heart in San Francisco.” Grab your friends and family and celebrate the season Tony Bennett style!
Breaking Up is Hard to Do Jan 19 to Feb 17
This nostalgic musical comedy celebrates the timeless songwriting magic of the legendary Neil Sedaka! Set at a Catskills resort in 1960, this humorous and heartwarming musical follows two friends from Brooklyn in search of good times and romance over one wild Labor Day weekend. Featuring twenty of Sedaka’s most popular songs including “Laughter in the Rain,” “Where the Boys Are,” “Sweet Sixteen,” “Calendar Girl,” “Love Will Keep Us Together” and the chart-topping title song!
Five Guys Named Moe March 15 to April 20
Jump into this swinging, high-energy Broadway musical set to Louis Jordan’s iconic rhythm and blues/jazz score! Nomax’s world has been turned upside down and all he needs is the right music—and the right guys—to get him through. Enter five guys named Moe, stepping out through his radio to cajole and comfort him with dozens of whimsical hit songs from the extraordinary Louis Jordan. An international sensation, Five Guys Named Moe is a musical fantasy that delivers sheer joy and exuberant entertainment!
George M. Cohan Tonight! May 10 to June 9
Meet “The Yankee Doodle Boy” himself in this high-energy, one-man journey through the life, music, and artistry of this legendary entertainer. This Off-Broadway musical is a delightful salute to the man who almost single-handedly invented the American musical comedy! Featuring tons of tap dancing and hit songs including “Give My Regards to Broadway,” “Over There,” “You’re A Grand Old Flag,” and “All Aboard for Broadway!”