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
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax,...
Duration:2 hours
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...
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...
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, ...
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