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Page 4 of 15 • 342 listings
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Caley
Beautiful Ranger 22 Sailboat for rent in Chicago 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!

Ben
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!

Matthew
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
The boat was great, fit our party of 12 well! Shay was communicative and flexible with the itinerary, and Captain Scott and Dave made our day on the boat a blast.

Sharon
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Captain Bob was friendly, professional, and made sure my husband and I had the best time. We enjoyed seeing the spectacular Chicago Skyline and Navy Pier Fireworks from a prime spot on the lake. Captain Bob’s experience also made us feel at ease, especially being on the lake at night. Highly recommend Captain Bob!
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Shahzeb
Good Vibes Only Aboard This Spacious 34’ Silverton Yacht
This was a very fun experience! The boat was super nice and had a lot of space for our group to spread out. Booking was very easy and Candice was very accommodating of our time. Would definitely book again!
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Amanda
21ft SeaRay SunDeck for Pewaukee Lake. Other lakes by request.
Kevin was the best captain. We used Kevin for my sister's bachelorette party and Kevin was by far the best choice we could have made. Kevin was super friendly and helpful. He treated us like a member of his family and went above and beyond to make sure we have the best time. His boat was very nice, clean, and spacious for 12 girls lol. Kevin was very familiar with the area and took us to all the best spots. We will definitely be hiring him for future trips!