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Page 8 of 10 • 240 listings
24
Detroit
Michigan
13
Saint Clair Shores
Michigan
9
Holland
Michigan
12
Norris Lake
Tennessee
281
Chicago
Illinois
10
Knoxville
Tennessee
78
Mississauga
Ontario
8
Lake Anna
Virginia
7
Kenosha
Wisconsin
10
Etobicoke
Toronto
17
Old Hickory Lake
Tennessee
69
Toronto
Ontario
19
Hendersonville
Tennessee
165
Potomac River
United States
57
Lake Norman of Catawba
North Carolina
7
Mount Juliet
Tennessee
29
Arlington
Virginia
62
Mooresville
North Carolina
CS
Crystal
Cruisers Y3375 Express Yacht Downtown Chicago Experience
Me and my friends had a great boat ride! Ramsey was extremely easy to communicate with and was very responsive throughout the entire process. He even FaceTimed us to walk us through how to setup the Bluetooth because we weren’t able to get it to work while on the boat. I would definitely recommend this boat charter and Captain Sam for your operator!

Kathy
39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included
George and his boat crew were absolutely amazing! We had such a fun time out on the boat and couldn’t have asked for a better experience. Everyone was friendly, welcoming, and made sure our group was comfortable and having a great time from start to finish. The whole experience was easy, fun, and memorable. We’ll definitely be booking with George and his crew again and would highly recommend them to anyone looking for an amazing day out on the water!
KT
Ken
Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests
Captain Mike is AMAZING!! He was incredibly accommodating, patiently waiting for our late arrivals and working with us to chart the perfect route so we could hit every spot on our list. Even through choppy waters, he expertly handled the boat to ensure a smooth and comfortable ride, all while keeping safety his top priority. An exceptional captain and host—he’ll absolutely be our first choice for our next outing!
SD
Sam
Chicago looks better from the deck of 45' Rinker Motor Yacht
Gill and Captain Maurice made chartering a boat so easy and stress free and were so accommodative. They worked with us to find a better departure time when the morning weather was a bit iffy and overall made the whole charter so smooth and fun! Highly recommend!!
JP
Joon
Now to End of Season Discount! All Included! 42 Sea Ray Sundancer Pure Luxury.
Captain Anthony and his crew were amazing and provided my group and I an experience we will never forget! They were very professional and safety-oriented while being easy going and making sure everyone was comfortable and safe. He educated us about the water and kept an eye on everyone in my group. Everyone had a wonderful time and we will definitely be booking through him again. The marina at navy pier is also small compared to other nearby harbors which makes it very easy to find the boat and load and unload things. It’s also minutes away from the playpen so you will have no time wasted!
HB
Haniyyah
Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht
Thank you for an amazing experience! My friends and I had a fantastic time on Lake Michigan. The boat was clean and well-maintained, the sound system was great, and our captain was professional, friendly, and made sure we had an incredible time. Everything on the water exceeded our expectations.