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Page 18 of 18 • 413 listings
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Ali
Luxury 24' Monterey Private Yacht - Chicago River, Skyline & Playpen Fun
Tamer was amazing we did the lake and river tour and it was awesome highly recommend
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Fanta
Luxury 24' Monterey Private Yacht - Chicago River, Skyline & Playpen Fun
The tour was amazing! Tamer was so fun, friendly, and made the whole experience even better. Thank you!
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Caley
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

Tonu
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!
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Yousuf
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!

Kimberly
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!