The Best Boat Rentals Near Winthrop Harbor

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!

44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available

Capt. Tim and crew were very accommodating and helpful. We rented the boat to scatter a loved ones ashes close to Navy Pier. Capt Tim was very receptive to our feelings and knew actually what we needed. We had a great celebration of life on his boat!

28ft. Sea Ray Captained Boat Rental in Chicago

Our party of 4 had a great time on Captain Memo’s boat. He was very communicative and sent a helpful video on where to find the marina. He also took pictures for us and sent them promptly following the ride. He made us feel very safe and welcomed.

27 ft Sea Ray, Captain Included

Bobby was the best captain! We left right on time and the water was beautiful. He had a cooler with ice prepared and ready for us upon arrival, and made the whole trip a time to remember! I could not recommend him enough!

Manitou 23ft Pontoon on the Milwaukee River

Ryan provided an excellent tour of the Milwaukee river. He’s very personable and informative and my crew thoroughly enjoyed themselves. I highly recommend him as a captain, we will definitely hire him the next time we’re in town.

28ft. Sea Ray Captained Boat Rental in Chicago

Captain M was great!! On time, had us laughing and very personable! Boat was perfect for a relaxing day on the lake with a group of friends