The Best Sailboat Rentals in Michigan

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!

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

We loved our experience with Nijole. They took us all around the lake and we loved every minute of it. We even got to swim! They are also a very fun time to hang out with and enjoy the day. Definitely recommend and we will be booking with them multiple times this boating season.

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

Nijole was incredibly helpful, communicative, and kind. She was responsive and went above and beyond to help us reschedule when bad weather struck. We had a lovely trip and she and her husband were delightful to be around! I highly recommend their boat and I can’t wait to sail with them again sometime.