Tall Ship Adventures of Chicago

Chicago, Illinois

About Tall Ship Adventures of Chicago

Each day of our daily and weekly sailing schedule is unique, with every trip dependent on the direction of the wind. No two tours are alike. Each sail also has a tour theme led by our enthusiastic crew-educators! Our tall ship crew are multi-talented individuals, many of whom have experience in the study of history, maritime lore, the arts, music, and theater- ready to bring their experience to enhance your enjoyment aboard Windy! You can simply relax on deck in quiet, or gather around for storytelling and hands-on fun!



Architecture Sail/Sailors Quest

DOUBLE FEATURE! Study the skyline from a beautiful lakefront vantage point to learn about the people, plans, and persistence that shaped Chicagos most famous sights.

Terms & Conditions

CANCELLATIONS: Charters can be cancelled for a partial refunded, a five percent (5%) processing charge will be applied if charter is cancelled more than 4 weeks before sailing date. Every effort will be made to reschedule a postponed charter, at no charge. If your group cannot reschedule: Cancellations 4 weeks before the charter date, will be charged 25% cancellation fee. Charters cancelled two weeks before the event will be charged 50%. Cancellations less than 72 hours before the event will be charged in full. If the Captain cancels for any reason, unforeseen circumstances or inclement weather, a full refund is given.

If Captain cancels for inappropriate or illegal behavior, no refunds will be given.

WEATHER: Cancellations due to weather will be at the Captain's discretion. Inclement weather is defined as cold or stormy conditions which exceed the average passing summer shower, and require more than a season-appropriate jacket. The charter leader will be notified within 2 hours of the charter if there is a threat of weather cancellation if possible. Very few charters are cancelled due to weather, and it is possible to set up a drizzle proof tarp on the main deck in case of a passing shower. However our sincere desire is that you have a pleasant experience aboard, and we will do our best to have your charter proceed as planned on that day.