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Special Event Sails in Chicago, IL

Browse our currently offered special event sails and experience a truly one-of-a-kind sail on Chicago’s lakefront.

From $79 $59 per Person

Chicago’s famous 2 hour Pirates Pub Sail departs every Friday night at 9pm aboard Tall Ship Windy at Navy Pier. Yes, this is Chicago’s Famous and Only Floating Pirates Pub!

Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. Your ticket includes up to four complimentary beverages; beer, soda or water, per person.   You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan.  Chicago’s famous Pirates Pub Sail is an event that should not be missed.

  • VIP Event - One Day Only!
From $49 per Person

This is the don’t miss sail of the year, Tall Ship Windy’s Labor Day End of Summer Celebration Sail. Departing from Navy Pier at 8:45pm, celebrate Labor Day, and for some the end of Summer, with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.