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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 - Limited Availability
From $134 per Person

Watch the 2023 United States SailGP Chicago races from the water aboard Tall Ship Windy, departing from Navy Pier. Windy is spacious, with three decks: the fore deck, midship deck and aft deck for unique viewing opportunities.

From $99 $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. 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.