Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!

Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!

Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!

Wonderful trip to honor my father who passed away, and who loved sailing on Lake Michigan in the 1950s on his small sailboat. The boat was just large enough to accommodate the 3 of us, which was perfect - a large vessel or motorboat would not have been pertinent to my father's history. Ben was easy to talk to and understood the importance of what we were doing, which made it all the better. Unforgettable trip.

This was our 1st sailing experience and we enjoyed it very much. We couldnt ask for a better captain. Ben was very accommodating and friendly. We were very happy with our experience and learned a lot about sailing in our short time on the lake. We highly recommend sailing with Captain Ben!