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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.

  • VIP Event, 1 Night Only
From $119 per Person

A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Order a cool drink from our bar, then relax, and enjoy a leisurely evening watching the best Fireworks display in the city.

Chicago’s Fourth of July fireworks is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, is truly a VIP event. This event sells-out early. For 2022, Chicago’s 4th of July Weekend Fireworks Will Be On Monday July 4th.

From $79 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.