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Page 2 of 10 • 240 listings
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KM
Karlie
50' Sea Ray Sundancer - 12 Passengers in Chicago, Illinois
This could not have been a better experience booking with Captain Carlos! We had a group of 20 girls for a bachelorette and booked two of his boats to take out and tie up together. His team was professional and ensured we had an amazing time. The boats we rented were clean, spacious, and had awesome speaker systems. Definitely the highlight of our weekend!

Sandra
50' Sea Ray Sundancer - 12 Passengers in Chicago, Illinois
I would highly recommend booking with Captain Carlos. He made the experience stress-free by being great about communicating. The boat is absolutely beautiful and had more than enough room to accommodate all 11 of us. We hired Captain Moni as the driver of the boat and he brought along Lala as a deckhand. Both were SO sweet, personable and made the whole experience that much better. I would recommend this team to anyone booking a boat in Chicago.

Kelly
50' Sea Ray Sundancer - 12 Passengers in Chicago, Illinois
Captain Carlos and his team were absolutely wonderful! Captain Mike cancelled on us 2 weeks out (and never bothered to text us and let us know) so we ended up scambling 5 days before our event without a captain. Captain Carlos and his team went above and beyond to make sure we didn't need to cancel our event, and ensured we had a fabulous time!
KF
Khari
Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
We had an amazing time out on the water thanks to boat owner Breanna and Captain Mike! From the moment we arrived, everything was handled professionally and with such a warm, welcoming attitude. Breanna made the booking process smooth and stress-free, and Captain Mike was outstanding—friendly, knowledgeable, and clearly experienced. What stood out the most was how safe we felt the entire time. Captain Mike explained all the safety protocols before we left the dock, and throughout the trip, he stayed attentive and in control. It allowed us to fully relax and enjoy the experience, knowing we were in great hands. The boat was clean, comfortable, and well-equipped. Whether you’re looking to cruise, swim, or just soak up the sun, this is the trip to book. We highly recommend Breanna and Captain Mike to anyone looking for a safe and unforgettable boating experience. We’ll definitely be back!
LV
Louie Chelle
42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!
We had an amazing time on Captain John's yacht! The boat was very nice, spacious, and exactly as described. It was perfect for a group of girls celebrating a college reunion! Captain John helped coordinate and get us set up right before takeoff, then we had Captain Dee and Hussein with us for the ride. They were all great and courteous! FYI - you will need to reach out to their list of captains to confirm (this was told to us the week of), but honestly, it sounded like they made sure someone was available regardless, so likely a formality. Definitely would book again for future Chicago trips!
KD
Kevin
42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!
Used Captain chris and he was great. I wasn't aware that there was a whole team required (3 people total including captain), not that it mattered much. They tried to not let us use the lilly pad because they said the wind caused it to float away with 8 people on it, but we were in the water and it was great. I would not want to hit the play pen without it IMH. John was very kind, and the boat was quite spacious. Overall had a great experience, 5 stars, but noting the lily hiccup that I felt like I had to fight to keep but it appeared to have no issues using it. Would book again