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Help us make it rightWelcome to Go Sailing Chicago. Whether you want a romantic sailboat charter for two under the stars, to go sailing along the Chicago skyline with friends, to learn sailing with the friendliest instructors in the city, or enjoy some quality time with family while the sun sets, Go Sailing Chicago has the right Chicago sailboat charter or sailing lesson option for you. We sail in Chicago from the...
Chicago Sailing and Sailboat Charters out of Monroe Harbor right downtown. We offer private fireworks charters, day sailing, night sails and much more.
My wife and I took an intro 101 to sailing, it was a great experience overall, Capt. Matt did a wonderful job in explaining different parts of the sailboat and how they work together. Very through...
Captain Tom was excellent. We learned a lot and had a great time. The team at Go Sailing was very accommodating getting me prepared for my lesson. We didn't have hardly any wind however, so while...
Whether you want a romantic sailboat charter for two under the stars, to go sailing along the Chicago skyline with friends, to learn sailing with the friendliest instructors in the city, or enjoy some quality time with family while the sun sets, Go Sailing Chicago has the right Chicago sailboat charter or sailing lesson option for you.
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