Lake Michigan, US Boat Rentals & Yacht Charters

Lake Michigan Reviews

1. dr

   david

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.

2. RJ

   Robert

   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.

3. BG

   Bradley

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   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!

4. 

   Beth

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   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!

5. 

   Danielle

   46' Luxury Yacht! Price all inclusive!

   We had the absolute BEST experience with Captain Terry and Vanessa on our Lake Michigan boat charter in Chicago! From the moment we stepped aboard, we were warmly welcomed and felt completely at ease. Terry and Vanessa are not only experienced and professional, but also genuinely kind and fun people — they truly made our time on the water unforgettable. Their boat was beautiful, clean, and incredibly well-maintained. You can tell they take pride in every detail. We especially appreciated how safety-conscious they were, which made it easy for us to relax and enjoy the ride. They gave us the perfect balance of hosting and letting us do our own thing — we never felt rushed or restricted, just completely cared for and free to enjoy the experience. We had such a wonderful time cruising along the Chicago skyline and taking in the amazing views. Whether you’re celebrating something special or just looking to enjoy a peaceful and memorable day on the lake, Terry and Vanessa are the crew you want. We would absolutely book with them again and highly recommend them to anyone looking for an exceptional boat day!

6. AB

   Ashley

   46' Luxury Yacht! Price all inclusive!

   Terry and his wife made are trip amazing. They were super polite and helpful the whole trip. They took us out on the lake and gave us a nice small tour. We arrived 30 mins late and they were kind enough to still give us our full time. I will be booking with them again.