Cruises, Sailing & Water Tours >> Sailing Trips
The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, ...
Duration:1 hour 15 minutes
A Truly Special Event Sail! During the summer, every Wed & Saturday night, Tall Ship Windy sails from Navy Pier for our ...
Duration:1 hour 30 minutes
Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the wor...
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax,...
Duration:2 hours
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, ...
The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday from Navy Pier. Leave...
Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foo...
Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan aboard Ch...
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. O...
Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick b...
Some popular Sightseeing Tours, Activities and Holiday Packages.
Duration : 6 Nights | 7 Days