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Page 2 of 12 • 287 listings
13
Lake Geneva
Wisconsin
8
Williams Bay
Wisconsin
9
Milwaukee
Wisconsin
9
Holland
Michigan
349
Lake Michigan
United States
8
Madison
Wisconsin
7
Toledo
Ohio
12
Glen Lake
Michigan
29
Detroit
Michigan
21
Torch Lake
Michigan
15
Saint Clair Shores
Michigan
14
White Bear Lake
Minnesota
22
Minneapolis
Minnesota
24
Minnetonka
Minnesota
10
Excelsior
Minnesota
10
Wayzata
Minnesota
60
Lake Minnetonka
Minnesota
13
Spring Park
Minnesota

Cheri Ann
Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests
Chris and his lovely wife hosted my family of 6 on their vessel for the 4th of July. He stayed in constant communication before the trip and also discussed the weather. He offered ideas for the perfect 5 hours on the Lake, and was not wrong. The couple was the perfect host. Their boat was beautiful. They gave us the best day!
AL
Alex
Captain and Fuel Included | Carver Mariner 350 | Private Chicago Yacht Charter
Absolutely amazing experience from start to finish! From the moment we stepped onto the boat, the crew greeted us so warmly, showed us where to put our things, got us settled in, and made sure we were comfortable before we set off. They ran through the basic rules in a friendly, easygoing way, and you could tell right away these are down-to-earth, genuine people. It honestly felt like being welcomed by family. The boat itself is gorgeous. It's calm, incredibly spacious, and honestly the photos don't do it justice — it's even bigger than it looks, and the inside is beautiful. There's so much room whether you want to sit up front, in the back, or relax inside, so there's plenty of space for friends and family. The scenery was stunning the whole way through, and everyone in my group loved every minute of it. This was the best 4th of July I've had in a while, and I'm so glad we got to spend it with them. I really appreciate how friendly and welcoming they were. I'll absolutely be coming back in the future — thank you so much for such a wonderful time. Highly recommend!
MF
Maxine
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was an incredible host/communicator. They made the booking and the trip easy, care-free and relaxing. The boat, The Harmony, was beautiful and clean. My fanily and I had an incredible experience and are excited to book another excursion soon!
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.
SC
Santhosh
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
We had a last minute booking and Nicole was kind enough to accommodate us and communication was great. Amazing boat, super friendly couple who are great to have conversations with. They made sure everyone had a great time safely. Highly recommend!