Set Sail with 36' Sailing Boat in Downtown, Chicago

Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.

Ray and Cassidy were very friendly, and allowed us to help sail the vessel as we requested. Ray is very qualified and enjoys sailing. I'm sure we could have laid back and relaxed as they did all of the work, but I think our experience was much better for having been more involved. Thanks, and we'll definitely use Ray again if we are back in the area and have the chance!

I can’t say enough for how great my experience was with Captain Ray, Captain Dawn and Captain Ted. From the initial booking all the way through the actual sailing, they were responsive, accommodating and amazing to work with. My fiancé and I did our engagement photos aboard Siren Song and the experience and photos exceeded everything I dreamed this day and these photos could be. Highly recommend!

Ray and Dawn were excellent, professional captains. We departed around 6pm and took a lovely sunset trip around the harbor. Unfortunately the winds were a bit too high to sail further out onto the lake, but we all appreciated the safe and relaxing trip. Highly recommend!

Ray and Dawn were excellent captains and hosts to our group. The boat was very cozy and we had a fun time being right in the action of the sails. If you book with Ray absolutely make sure you get your sail time in! Even if you're heading to the playpen, take the long route so you can enjoy the peace and quiet of Lake Michigan.