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:
2026
2027
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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
2026
Never Can Say Goodbye: The 70s Beehive Musical August 7 – August 30, 2026
Southeastern Regional Premiere! Put on your platforms, shades and bell bottoms and get ready to party! This new musical celebrates the iconic sounds of the 70s that defined a generation. Featuring a cast of 6 incredible women singing more than 30 well-loved songs by Heart, Fleetwood Mac, The Jackson Five, Diana Ross, Linda Ronstadt, Gloria Gaynor, and many more.
The Rat Pack Lounge – Sept 25 to Oct 18
Come swing, sing, and savor the days of highballs and high rollers! After Frank, Dean, and Sammy leave some unfinished business on earth, God sends them back for one night to make things right and fulfill their promise to the owner of the Rat Pack Lounge. This musical comedy features the Rat Pack’s greatest hits including “My Way,” “Come Fly with Me,” “Ain’t That a Kick in the Head,” “Everybody Loves Somebody Sometime,” and many more!
A Christmas Survival Guide – November 20 – December 20, 2026
Do the holidays stress you out?! This light-hearted musical comedy is designed to de-stress and refresh one and all with holiday cheer! Armed with a copy of “A Christmas Survival Guide,” the characters charge into the holidays searching for the true meaning of the season. Featuring well-loved songs, mashups of old classics, and wonderful comedic originals, you’ll learn how to survive the season in ways that are both hilarious and heartwarming.
Now Comes the Fun Part – The “How the #@&! Did I Get This Old?” Musical – January 22 – February 14, 2027
Southeastern Regional Premiere! This laugh-out-loud musical dives into the appalling indignities and rude awakenings awaiting anyone lucky enough to make it past that dreaded AARP birthday. From early retirement to the first colonoscopy, from empty nesting to dating again, this new musical is a hilarious celebration of life’s third trimester. You’ll laugh… you’ll cry… you’ll throw out your back laughing and crying! And if you can’t relate to any of this now, don’t worry—you will soon.
