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Pirates of Penzance – Tall Ship Windy | Navy Pier

Dinner and a show, dinner cruise … feel a little old hat, right? If you think your date night or next family outing could use some oomph, then how about boarding the Tall Ship Windy for a night of sailing and opera!

For four special nights, the nautical production The Pirates of Penzance will unfold on board the Tall Ship Windy, the first time it’s ever been staged on a functioning Great Lakes tall ship!

The Pirates of Penzance, a Gilbert and Sullivan operetta which first debuted on New Year’s Eve 1879 in New York City, tells the light-hearted tale, through story and song, of an apprentice named Frederic who finds himself in a bit of a pickle. Apprenticed to a band of pirates, he’s released upon his 21st birthday and promptly falls in love with a young maiden named Mabel. The conflict arrives when Frederic reads his apprenticeship contract again and discovers that he was born in a leap year; according to the paperwork, he’s only worked for five birthdays and owes the pirate crew another 63 years. Will Frederic give in to his sense of loyalty and duty and work off his remaining years or ditch the crew and run off with his newfound lady love? That’s for you to discover with a ticket to The Pirates of Penzance!

Join the cast of professional singers and actors and the Tall Ship Windy’s own outstanding sailors for this spectacular 90-minute opera cruise that’ll be one for the history books!

Tickets cost $45 per guest and can be purchased online. Sail dates are as follows:

Saturday, September 1 at 5:45 p.m.

Sunday, September 2 at 5:45 p.m.

Saturday, September 8 at 5:45 p.m.

Sunday, September 9 at 5:45 p.m.

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