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    Barth Pond

    3.0 (2 reviews)

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    Tall Ship Windy - Tall Ship Windy

    Tall Ship Windy

    4.1(535 reviews)
    21.4 mi•Near North Side

    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.

    This boat ride was so enjoyable. The crew was awesome! Special shout out to Nina who went above…read moreand beyond to assist with my mom and aunt who are handicapped and had a great time. I highly recommend Tall Ship Windy!

    Photos
    Tall Ship Windy - Michael Charles & his group

    Michael Charles & his group

    Tall Ship Windy - Andy the Kidd, regaling the passengers with tale of lake piracy!

    Andy the Kidd, regaling the passengers with tale of lake piracy!

    Tall Ship Windy - Had the cruise actually been as advertised, we SHOULD have seen this!

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    Had the cruise actually been as advertised, we SHOULD have seen this!

    Barth Pond - boating - Updated October 2026

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