The Best Sailboat Rentals in Lake Michigan

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

Sail & Swim from a Luxury Sailing Yacht

We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

I was so happy to do this experience but I didn’t know that I was going to like it so much ! I would recommend having this boat for a 2 date or double date ! The owners are really lovely but the best part is going to the pope and sitting there ! Make sure you bring wine, glassware and whatever you want to have ! 2 hours was a perfect time for us! Us we were lucky enough to have of the best sunsets of the season !

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

I want to thank Nijole for her work . Everything was perfectly organized, swimming and sailing. My daughter got seasick and we received full support from the captain. There was also a miracle dog on board ! Dog swam with us and gave us a good mood! Thank you very much! If you want to have a wonderful time sailing, then you are definitely to Nijole! With respect, Vadim Pliss!