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.
Highlights
Tour Highlights:
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Current Show Schedule:
2025
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EscotGroups 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, EscotGroups by US Tours will be happy to structure tour prices to match your needs. Just let us know!
Itinerary
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 Descriptions
2024
2025
The Bikinis Jan 24 to Feb 22, 2025
Everyone’s favorite girl group from the 60s is back together again after twenty years and they’re bringing back the sun, fun and all the great songs they sang down on the boardwalk in 1964! With a show that promises to get everyone dancing in the aisles, the women relive their heyday and beyond, singing hits like “It’s in His Kiss,” “Yellow Polka Dot Bikini,” “Heat Wave,” “Under the Boardwalk,” “When Will I Be Loved,” “It’s Raining Men” and more!
Gigolo: The New Cole Porter Revue March 14 to April 12, 2025
An audience favorite from the Playhouse’s 1st Annual Florida Festival of New Musicals! Inspired by the life of Porfirio Rubirosa, Gigolo uses a collection of iconic Cole Porter songs to tell the tale of a jet-setting, international playboy and his relationships with four beautiful women. The outstanding score features 25 Cole Porter classics including “You’re the Top,” “Let’s Do It,” “Why Can’t You Behave,” “I’ve Got You Under My Skin” and many more!
Route 66 May 9 to June 8, 2025
Jump in the car and enjoy a high-octane musical celebration along the iconic Route 66! From the sounds of 1950s Chicago to the California surf music of the 1960s, this exciting musical features 34 of the greatest “Rock ‘n’ Road” hits of the 20th century. Songs include “Dead Man’s Curve,” “King of the Road,” “Little Old Lady from Pasadena,” “Fun, Fun, Fun,” and many more! Get your kicks with this smash coast-to-coast hit musical!