Tall Ship Windy, Chicago

About Tall Ship Windy

Tall Ship Windy is a 148-foot, four-masted schooner offering public sailing tours and special event cruises from Navy Pier. Visitors board the historic vessel for Chicago Skyline Sails, which provide views of downtown from the water as an alternative to typical motorboat tours. The ship hosts Chicago Fireworks Cruises for watching fireworks from the water, along with special event sails including live blues music on Monday nights and experiences during the Chicago Air and Water Show. Private charters and group sails accommodate various party sizes seeking customized outings. The vessel operates under USCG licensed captains with deep maritime experience. Guests can purchase individual tickets or select from seasonal memberships offering multiple sails throughout the sailing season, with some memberships including priority boarding and exclusive perks. Tickets are sold online through the venue's website.