The Best Boat Rentals Near Winnetka

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

My friends and I had such a great time on this yacht! The yacht was spacious and clean, perfect for our group to relax and enjoy the day. Everything went smoothly from booking to the very end. Kevin’s customer service was hands down the BEST I’ve experienced. He was responsive, helpful, and kept us informed every step of the way. Our captain, Evan, was just as amazing! The ride was smooth, safe, and so much fun. I highly recommend booking with Kevin, and I’ll absolutely book with him again when I return. Thanks for everything!

Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.

Diego was awesome and so was his boat! Four of us girls went out for the day and had the best time! Perfect size with plenty of space for 4. He also had a lily pad and a cooler full of ice, which was perfect! Diego is a safe, responsible captain always aware of his surroundings (and other watercraft drivers not paying attention), and made sure we were safely anchored in the playpen with plenty of space to enjoy ourselves and swim. Will book with Diego for my next boat outing & highly recommend!

28ft. Sea Ray Captained Boat Rental in Chicago

I can’t recommend Captain Memo enough! Not only did he go above and beyond to make my husband and I’s afternoon on his boat an awesome experience, he is also the kindest human! We had so much fun and will definitely be using him again. If you are looking for great captain, he is your guy!

28ft. Sea Ray Captained Boat Rental in Chicago

There’s not enough words to describe how great our experience was with Captain Memo. His communication was great. He was very knowledgeable of the water. Made our experience very memorable. If you’re looking to experience a wonderful yacht day Book now!!! Thank you Memo for going over and beyond to make sure we felt safe and have good time!!

28ft. Sea Ray Captained Boat Rental in Chicago

⭐️⭐️⭐️⭐️⭐️ We recently had the pleasure of going on a boat tour with Captain Nemo in Chicago, and we can't recommend it highly enough! From the moment we stepped aboard, Captain Nemo made us feel like family. The views of the skyline from the water were absolutely breathtaking, and the boat itself was comfortable and well-maintained. Captain Nemo's attention to detail and commitment to ensuring we had the best experience possible really stood out. Whether you’re a local or just visiting, this tour is a must-do! Thank you, Captain Nemo, for an unforgettable day on the water!

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.