Chicago Tall Ship Sails with Tall Ship Windy

Chicago’s skyline and Lake Michigan form a striking backdrop for an experience aboard the Tall Ship Windy, a living piece of maritime heritage. Operating from May through October, Tall Ship Windy offers a lineup of adventurous sails that blend education, celebration, and scenic cruising on the water. From seasonal highlights like the 4th of July Independence Sail and the Air & Water Show special events to weekly rituals like the Monday Night Blues Summer Concert Series, this tall ship is an anchor for community and adventure on the lake. Visitors can choose from themed sails ranging from the educational Tall Ship Discovery Sail — where passengers learn the ropes, literally, raising sails and steering — to relaxed Fireworks Cruises that linger on the water after the show, perfect for unwinding under an expansive Chicago sky.

Tall Ship Windy stands out as a unique fixture in Chicago’s outdoor recreation scene by offering a hands-on, authentic sailing experience on a classic tall ship. The ship’s attentive, approachable crew ensures passengers of all ages feel welcome to participate or simply savor the sights: the city skyline’s striking skyline architecture, the shimmering lake waters, and the dynamic activity of the harbor. The diverse craft events hosted onboard highlight Chicago’s connection to the water—its history, culture, and community spirit.

Navigating the winds of Lake Michigan, the ship’s wooden decks, its rigging, and canvas sails provide more than a ride—they offer a chance to connect with Chicago’s maritime legacy and embrace the outdoors in a fresh perspective. Whether you sail during the radiant summer months or the crisp fall evenings, Tall Ship Windy presents a dependable, refreshing escape from city life and an immersive way to experience the coastline’s natural and urban intersects.