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Page 6 of 10 • 237 listings
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Karen
New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain
The boat was gorgeous and had lots of room for lounging, relaxing. The captains were polite and attentive and helped the experience to be easy and stress-free. Lots of built-incoolers on board the boat as well. Would definitely book again!
MD
McKenzie
See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht
We had an amazing experience renting this boat for our bachelorette trip! The boat was beautiful, spacious, and perfect for our group. The captains were fantastic and made the entire day so much fun. We especially loved the floating mesh lounge, it was such a great addition and gave us the perfect place to relax in the water. We had an incredible time and would absolutely recommend this experience!

Kristin
See the Chicago’s Stunning Lakefront Aboard 46ft Sea Ray Sundancer Motor Yacht
Absolutely fantastic experience from start to finish. Kevin was incredibly fast to reply to every message, booking was seamless and he answered all of my questions right away, which made planning so easy. The boat itself was amazing. It’s very roomy, with plenty of space to spread out and relax, and it’s loaded with amenities. Everything was clean, well-maintained, and exactly as described. We couldn’t have asked for a better day on the water. Highly recommend Kevin and this charter to anyone looking for a great time, we’ll definitely be booking again!
LR
Lindsey
Private Boat Charter - Sea Ray 390 Sundancer In Chicago
Our boat ride with Margaret and captain Bob was perfect, we had so much fun on their boat. They provided a very fun and safe ride with my friends for a birthday celebration. Would recommend to anyone!
AS
Andy
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!
TW
Ted
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.