The Best Yacht Rentals Near Woodbury

51ft Sea Ray Sundancer Yacht at Diversey Harbor!

Can’t speak highly enough about the professionalism. The captain prioritized our safety, communicated clearly, and made sure everything ran smoothly from start to finish. It was my first time, and I couldn’t have asked for a better experience — truly 10/10 across the board. Grateful and impressed! He also made us feel completely at home and comfortable throughout the entire trip. I’ll definitely be booking with him every time. The boat was exactly as advertised — clean, spacious, and just what we were looking for. Highly recommend!

48ft Regal Commodore for rent in Milwaukee

💯 percent recommend booking with Capt Dan and Jen. They were great communicators and safety was definitely their priority. They very interactive with the group and promptly addressed all of our concerns. I highly recommend booking with them. Thanks again for everything

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

Great service great crew great experience! Michael was a very helpful and very nice deckhand! Captain Natalia was very experienced informative and thorough making sure we all made it back safe. Can’t stop hearing “3 points of contact!” in my head lol love it! Will be booking again soon.

Experience the Best of Chicago on a 30ft Sea Ray Sundancer

We had such a great time, Gina was soo good about making sure she answered all our questions promptly via text. I was soo nervous about things going smoothly and she helped execute our plan flawlessly. She even took pictures and videos of us and sent it to us after. We couldnt have asked for a more perfect experience. Thank you Gina and team for making my husband's 40th birthday so memorable <3

28ft. Sea Ray Captained Boat Rental in Chicago

Captain Memo you were awesome!! Thank you for the charter. The boat was great, you were great, the day was great! If you’re looking for a nice day out on the water with some friends/family look no further. Truly, we highly recommend using Captain Memo. Out of everyone, he was the most responsive and was an overall great person. Our group had a blast with him! Thank you again!!

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!