Chicago Sailboat Charters

Great excursion!

My husband and I had a great experience on today’s 2hr sailboat ride. Dennis was our captain and was very informative, friendly, and put safety first. I would highly recommend this company and already...

Buy buy buy, sail sail sail

A perfect occasion, a perfect Saturday morning and a wonderful captain (Bill) made this private sail the buy of a lifetime. Cannot wait to do it again.

Wonderful end to a wedding weekend!

We went on a Sunday afternoon. Despite an ugly forecast for a few days prior, the weather was beautiful! We rented the Big Boat for our 30 person trip. They were very accommodating....we brought bl...

Relaxing few hours on the water

Easy too reach from Lake Shore Drive. Captain Steve was excellent. Bring your own wine and beer-they don't like red wine in case it spills.

Captain Patrick was great

We rented a motor boat for a party of 11 to host a relatives "memorial". The boat company did a wonderful job working with us. We left countless messages for other companies, but this was the only o...