Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official ... More

The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operatio... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More

The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday from Navy Pier. Leave the hustle and bustle behind, and enjoy a leisurely Educational Sail aboard Chicago’s Official Tall Ship. ... More

A Truly Special Event Sail! During the summer, every Wed & Saturday night, Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. Enjoy the amenities of the 148 foo... More

Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied ... More

Enjoy a private two-hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.... More

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyli... More

Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan aboard Chicago's Famous Pirates Pub. Your ticket includes one complimentary rum punch, domestic beer, soda or water, p... More

Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacul... More