The Best Boat Rentals Near South Haven

Sail & Swim from a Luxury Sailing Yacht

This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

Martin and his vessel were very well kept. The list of captains provided were very professional and polite. Martin was very prompt with communication and worked with each change needed through the process of scheduling the trip. I would very much so recommend him and his services. The trip was a success and enjoyable

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.

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

Martin's boat is great for a day on the water! It fit 12 of us comfortably. We were able to go from Belmont Harbor to the Playpen with plenty of time to swim and relax before having to head back. Also, Captain Matt and Jamie were awesome! They were looking out for both our fun and safety the whole time we were on board which was greatly appreciated.

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!