1. Tower Road Beach

    1. Tower Road Beach

    0

    Winnetka, IL

    Tower Road Beach

    3.2 (10 reviews)

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    Tall Ship Windy

    Tall Ship Windy

    4.1
    (532 reviews)
    16.8 mi
    Established in 1996
    Family-owned & operated

    One of the best things I did while visiting Chicago! I booked the 8:30 p.m. Tall Ship Windy sail,…read moreand it was worth every penny. We left around 8:30 to 8:45, and by the time the 9:00 p.m. fireworks started, we had a front row view from the water. It was absolutely incredible. The captain and crew were friendly, welcoming, and did an amazing job. The ship wasn't overcrowded, so there was plenty of room to walk around and take in the views. Watching the fireworks with the Chicago skyline in the background was unforgettable. After the fireworks, we sailed under the night sky with the sails up and great music playing. It honestly felt like I was in the Caribbean, except with an amazing city skyline all around us. I'm from New York and was in Chicago for work, and I have to say this was even more impressive than seeing the New York skyline from the water. I also own a sailboat, so I really appreciated how well the crew handled the ship. One of my favorite parts was that guests could even help hoist the sails. There was a full bar with a really good rum punch, and so many great spots to take pictures of the sunset and the skyline. The crew was also happy to take photos for people. If you're going, get to Navy Pier early and enjoy the restaurants and drinks before your sail. This is great for families, couples, or even if you're traveling by yourself like I was. It's a unique experience that you won't get on one of the regular tour boats. I would absolutely do this again the next time I'm in Chicago.

    Staff was so amazing and kind, relaxing way to see the city on a calm and quiet sailboat so much funread more

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    Tall Ship Windy
    Picture you take prior to boarding. You can purchase these once you return to Navy Pier
    Picture you take prior to boarding. You can purchase these once you return to Navy Pier
    The Tall Ship Windy at dock

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    The Tall Ship Windy at dock
    Radiance Charters

    Radiance Charters

    4.7
    (3 reviews)
    11.6 mi

    We had a great charter on the Radiance recently! Captain Ben was super nice and informative,…read morepatiently explaining to us some of the basics of sailing. He and the first mate also let us help with some of the sailing tasks. The Radiance is an impressive boat, and even with light winds, we got a good taste of sailing on Lake Michigan. An added bonus is launching out of Montrose Harbor, which is surrounded by a park, golf course, nature trail, food spots and places to swim.

    Well this review is about a month overdue but I had to write one for Captain Ben and Radiance…read moreCharters for the amazing experience I and my friends had. We were a group of 6 and looking for a weekend 2 hour sail. Since I was booking last minute, most of the other charters I enquired were either booked or quoted jaw dropping rates. Captain Ben accommodated us all on his amazing race boat at a fairly reasonable rate. He is a professional racer and it showed when he cruised the boat in fast into Lake Michigan., much to our thrill. We took out own beer and some food. He provides you with drinking water and a place to cook too. Captain Ben is an instructor too so its fun learning the basics if you're a first timer. Wish we could do longer but with friends flying out and everything, we could sail for only 2 hours. But it was an amazing experience and my friends loved it. We will definitely go back.

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    Nothing better than dangling toes on a hot day!

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    Nothing better than dangling toes on a hot day!

    Tower Road Beach - beaches - Updated July 2026

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