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Page 2 of 17 • 402 listings
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Trey
Prestige 550 Flybridge Luxury Yacht Charter in Chicago
This boat is incredible. More than enough room for a full charter. The weather wasn't the best, but we still had an amazing experience. Captain Matt was great, him and Will made sure we maximized our trip. Would recommend for anyone looking to have a great time.
JR
John
Barletta EXQ23 Expanding 25' Pontoon Boat with Captain Pete on Cass Lake, MI
Captain Pete Was Amazing. We felt completely secure the entire time, especially when boarding and moving around the pontoon boat. Great Local Knowledge: He knew all the best information catering to our crowd. Stress-Free Vibe: He handled all the navigation, anchoring, and gear so our group could just relax and have fun. Wonderful with Everyone: He was friendly & patient. If you want an easy, and memorable boat day, book Captain Pete! Five stars! Highly recommended.

Jennifer
Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.
JJ made our entire birthday weekend. He was very communicative and evaded a thunderstorm for us, pivoting to a better time the next day. The boat is luxurious and so comfortable. He customized our experience with joy and conviction. We had so much fun and felt safe and cared for. Book JJ. Now.
HS
Heather
Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.
Everything about JJ’s boat and the overall experience was 5/5 ⭐️. The boat is super comfortable for a group and perfect for swimming or just lounging around. JJ is an excellent captain, great communication. We had an amazing time watching the air and water show practice. Will definitely be booking again!

Barb
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!
SG
Samantha
Diversey Harbor: 36' Sea Ray Floating Oasis for your Unforgettable Celebrations
This was the most fun I’ve had in Chicago so far, the weather was beautiful and we had a smooth ride. We rented the boat for a bachelorette and communicating with Kevin was so easy, he was able to answer all of our questions patiently, he was so kind and made the whole process so easy. Our captain was Riley, I would totally recommend him, he was puntual, funny and made our trip so fun and also made us feel so comfortable and safe. He was clear with instructions and was patient with us as well. I would totally recommend Kevin and his boat to everyone!