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Page 2 of 17 • 406 listings
AK
Augusta
Private Cruise onboard Hunter Legend Sailboat in Chicago
We had a great first experience sailing with Capt. Will and Justin, we felt safe and all our needs and preferences were accommodated, we had great views of the skyline, and the crew had a lot of knowledge and stories to share. Would absolutely do this again!
BJ
Brittany
Private Cruise onboard Hunter Legend Sailboat in Chicago
Wonderful experience on the boat! We loved it from start to finish. The whole crew was friendly and hospitable. We all felt safe and secure and our journey on the lake was nothing short of beautiful. Everyone described it as a perfect day! Book with this crew if you’re interested in a welcoming, warm and accommodating experience tailored for your wants. Highly recommended.
S
Private Cruise onboard Hunter Legend Sailboat in Chicago
One of my favorite experiences out on Lake Michigan! In my opinion, there is no better way to see Chicago than at sunset on a sailboat. Captain and deck hand were professional, friendly, fun - and were part of what made the trip so special. Thank you!!
bb
bridget
27' Chris Craft with Water Toys plus Jet Ski Available
We booked a four hour trip for our family of four and absolutely loved it. We needed to reschedule our originally booked day due weather and Tim was very accommodating and flexible. Our experience on the water was perfect and exceeded our expectations for a family day out. I can’t wait to book again soon.
DJ
Dana
27' Chris Craft with Water Toys plus Jet Ski Available
Great experience! We had a wonderful and relaxing trip down the shore, taking amazing pictures. We really enjoyed just relaxing on the floatable and taking in the scenery. Tim was great too, communicating quickly and accommodating us when we parked in the wrong parking lot, causing us to be late. We would definitely rent with him again. It was an unforgettable day.
Sabrae
27' Chris Craft with Water Toys plus Jet Ski Available
Our boat ride with Captain Tim and first mate Diana was the perfect way to celebrate my husband‘s birthday. The boat accommodated the six of us perfectly allowing us to enjoy the ride together. We enjoyed the experience of going from the dock through the lake to the Chicago river and back. Captain Tim was able to expertly navigate the waters in spite of other boater’s behaving badly. We enjoyed Captain Tim allowing us to eat, drink and be merry for the whole ride. It was a beautiful night and he knew all the perfect spots for pictures. The next time I’m looking to rent a boat, Captain Tim will be my first choice!