Make your next group outing unique with a real tall ship sailing adventure! Tall Ship Windy is a majestic 148-foot four-masted gaff topsail schooner. Modeled after a traditional Great Lakes trading ship, she is built of modern materials but boasts all the character and charm of the Golden Age of Sail.
Bring your family, reunion, retreat, happy hour or celebration to Tall Ship Windy!
Whether you’re looking for hands-on adventure, intriguing history or a leisurely cruise, Windy has something for you!
Windy boasts three spacious decks, a grand salon, pressurized “heads” (marine toilets) and a bar for your enjoyment.
Plenty of deck seating is available on benches and boxes. The bar is stocked with soda, water, beer, wine, liquor and snacks. Ask about our bar packages!
We feature brands from local distilleries and wineries.
Windy’s signature programming combines exciting Great Lakes history with interactive storytelling for curious minds of all ages.
Our knowledgeable docents bring the history to life, so you can experience Chicago like never before.
On Windy, explore:
Our daily sailing schedule is always up-to-date on our website and is a great way to find a program that fits your group.
Discounts are not available for Educational Sails.
Weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more!
Windy can host up to 148 guests, including your caterer and musicians or talent.
Charter rates start at $4,000, dependent on event date and time.
Windy boasts three spacious decks, a grand salon, pressurized “heads” (marine toilets) and a bar for your enjoyment.
Plenty of deck seating is available on benches and boxes. The bar is stocked with soda, water, beer, wine, liquor and snacks. Ask about our bar packages!
We feature brands from local distilleries and wineries.
Caterers generally set up buffet-style in the grand salon, adjacent to the galley area, with guests free to move in and out.
Seating is informal on Tall Ship Windy, so “picnic-style” meals work best.
All catering vendors must be approved by Windy’s management before they can be hired. Please ask us for a list of our preferred caterers.
No alcohol can be included with catering as Windy is a registered bar and is licensed to accept and distribute only its own alcohol.
Beverage packages are available, starting at $12.00 per person, per hour. Please contact us for additional information.
With a storyteller on board, choose from programming options such as Chicago Architecture, Piracy on the Great Lakes, Chicago maritime ghost stories and more.
Live music is also available, or bring your own band on board. There is an additional charge for entertainment.
Questions? Contact us at 312.451.2700 for pricing, scheduling and more information.
Please visit our private charters page for more info.
You can purchase these optional items when you book:
Trip Insurance: $8.00 per person—gives you the ability to cancel your reservation if needed and receive a full refund. This applies up to 8 hours before your scheduled sail time or if Tall Ship Windy cancels your sail due to weather.
No refunds, no exchanges without the purchase of additional trip insurance: Rain or shine event.
No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
All sales are final. The captain reserves the right to postpone a sail for up to 120 minutes; if the sail is canceled, tickets may be exchanged for another time.
Take a relaxing sail along Chicago’s shoreline and enjoy breathtaking views of the skyline. Available daily, with special sunset and twilight options starting in September.
Set sail for a magical evening and watch Navy Pier’s fireworks light up the sky! Enjoy stunning skyline views, a relaxing sail, and a drink from our onboard bar.
Join us for a beautiful evening of blues music aboard the Tall Ship Windy on Lake Michigan, featuring talented artists like Grammy Elected Michael Charles.
Experience Chicago’s Air & Water Show from the Best Seat on the Lake! Great for friends & family!
Best View in the City Aboard 148 foot Schooner Windy
Sail into Independence Day aboard Chicago’s Official Tall Ship Windy! Enjoy patriotic music, stunning skyline views, and a festive evening on the water.