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    Two Brothers Sailing Adventures

    4.8 (12 reviews)
    Closed 8:00 am - 8:00 pm
    Updated 3 months ago

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    We went out with capt jeff this Monday for a wonderful cruise. The boat is awesome and jeff is an entertaining captain teaching us about sailing and letting my son take a quick swim. We brought food and couple of adult beverage and had a nice dinner and drinks. My daughter did get a little sea sick but that was the only thing that went slightly wrong. The Lake was awesome tonight with a great sunset. I would love to go again!

    Sunset cruise
    Tiffany K.

    Great event and awesome experience! Jeff is super friendly and helpful. He left me steer for a while until I almost crashed into another boat... Oops. But really it was so relaxing!! My husband commented that he felt like all his troubles were left on land. Sunset cruises are great. He helps you customize your experience and makes it so so breezy.

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    6 years ago

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    5 years ago

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    8 years ago

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    9 years ago

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    7 years ago

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    7 years ago

    Great time on the lake with Captain Jeff! It was the highlight of our girls weekend. Lisa B.

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    14 years ago

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    11 years ago

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    10 years ago

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    Review Highlights - Two Brothers Sailing Adventures

    Jeff is great very entertaining and engaging the 2 hour tour is great and at a very reasonable price.

    Mentioned in 7 reviews

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    There are many different boat tours out there with different prices and different lengths of time I…read morewould definitely recommend the architect boat river tour. I would say if you have 90 minutes this boat tour is a must do. I believe the option times that we had to choose from was anywhere from 10:00 a.m. for the first boat going out and the last boat was 4:00 p.m. but check the website for exact times. We booked our tour online to make sure that we got the time and date that we wanted to we preferred earlier in the day. We booked about 2 months out. These tours fill up quickly especially in the summer time. We started lining up about an hour before to make sure we got a seat up top so we could enjoy the view. If you prefer to sit inside you still will be able to hear the tour guy just you may not be able to see everything he is announcing it may be on the other side of the boat which you may not see if you're inside because of other people that are sitting. Our tour guide was wonderful explaining the different buildings and if you had any questions he would definitely answer those questions later on. This was my second time in Chicago I learned many new things by going on the tour I am glad that I did and I would recommend anyone else to do so as well.

    Two Brothers Sailing Adventures - boatcharters - Updated August 2026

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