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Top Chicago Sailing Trips
Private Evening Sail in Chicago Ending with Navy Pier Fireworks
2 hours - 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 skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable...Read more
Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
1 hour 15 minutes - 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.
Guests will enjoy 75 minute sail where they will learn about sailing and the history of Lake Michigan and Chicago....Read more
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
2 hours - 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 spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any...Read more
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
1 hour 15 minutes - 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 Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States....Read more
Chicago Skyline Sunset Sail Aboard Official Flagship of Chicago 148' S/V Windy
1 hour 15 minutes - 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 operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn...Read more
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
2 hours - 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. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect...Read more
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
2 hours - 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. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the...Read more
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
2 hours - 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. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect...Read more