Chicago Sailboat and Yacht Charters provide our guests with exclusive, private breathtaking charters that offer complete luxury, flexibility and customization. Take your family on a day cruise and experience Chicago like you never thought was possible, a priceless adventure. Charters can range from adventurous blue water sailing past the cribs of Chicago and into the deep blue waters of Lake Michigan or cruising along the lakefront and taking in some of the best views of Chicago.

The lakefront cruises take you from Belmont Harbor south along Lake Shore Drive take in an incredible view that can only be seen and appreciated from the water. We continue on past Oak Street Beach, into the protected area called the “Play Pen” for a swim and sun bathing. Then past the world famous Navy Pier, then back out into the lake and past the Chicago Lighthouse and one of the famous Chicago Cribs and back to the harbor.

Experience first hand the relaxing beauty of a peaceful sail on our 3-4 hour and all day Private boat Charter. We also offer a 3-hour Sunset Cruises, a perfect way to end the day with friends. Our sailing cruises are perfectly equipped to help you celebrate your special occasion; engagement, birthday or anniversary.

We can also sail North along the lakefront past Edgewater and all the way up to Bahia Temple in Wilmette on a full day excursion. Lunch, dinner and drink options are available. Our Charters range from 3 hours to a full day. By law we can only take out 6 passengers at a time. Point us where you want to go. We will take you where you want when you want and for as long as you want. Kindly be at the boat at least 15 to 30 minutes prior to your scheduled charter time.Sit back and enjoy a day on the lake. Our boats are in Belmont Harbor please see our directions page for directions to our slip.