By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Page 5 of 17 • 404 listings
TF
Todd
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.
JP
Jessica
Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht
We had a wonderful time on the boat. Our captains Peter & D were the absolute best- helped us get settled, were very professional yet relaxed, and covered us in when it started to rain. Boat was in fantastic shape, 10/10 would totally love to book again!!
WZ
Will
Sunseeker 70' Exclusive Motor Yacht - Perfect for Private Events in Chicago
The captain and crew were friendly, professional, and made sure everyone had a fantastic time. The boat was beautiful, well-maintained, and exactly as described. Communication was easy throughout the process, and the entire experience was smooth from booking to the end of the trip. Highly recommend for anyone looking to plan a fun and memorable day on the water!
SR
Steve (Kris)
Sunseeker 70' Exclusive Motor Yacht - Perfect for Private Events in Chicago
We had an amazing experience! The boat was beautiful, and everything exceeded our expectations. Captain Damian and Jules were both outstanding—they were professional, friendly, attentive, and made sure everyone in our group had a fantastic time. We even had a brief rain shower, but it ended up being a unique part of the experience watching it move across Lake Michigan. If you’re looking for a first-class charter in Chicago, I highly recommend them. We can’t wait to book again next year!

Melissa
30 foot Rinker Captain included in price!!!
Captain Joe was the perfect captain for our bachelorette party! He took all of the photos of the group we asked for, so kindly. He was attentive, but low key- and even navigated a surprise rain shower. Would 100% recommend him for any occasion.
MV
Mary
Manitou 23ft Pontoon on Okauchee Lake
Ryan was great! He was very personable and accommodating. He provided us with a fun and relaxing day to truly enjoy the lake and surrounding venues.