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All listings in Lake Michigan

Awesome cruising catamaran rentals in Lake Michigan, United States.

Page 1 of 13 listings

7 to 13 passenger Lake Michigan Sailing Charter
Sailing in Chicago · 13 guests

7 to 13 passenger Lake Michigan Sailing Charter

5.0
$550/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Best of 2025
$375+/hour
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Sailing in Chicago · 6 guests

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

5.0
$450/hour

Cruising Catamaran Reviews in Lake Michigan

  1. M

    Mark

    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.

  2. S

    Sandra

    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.

  3. J

    Jeff

    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.

  4. SB

    Susan

    7 to 13 passenger Lake Michigan Sailing Charter

    I would absolutely recommend everything about this experience. The boat was beautiful and very spacious. Captain Russell was wonderful to work with, very professional and a great communicator. Captain Brian was excellent at navigating wind and choppy water and was so much fun to have aboard with our group. Thank you again for a wonderful time!

  5. MD

    Morgan

    7 to 13 passenger Lake Michigan Sailing Charter

    Captain Russell was fantastic! When the weather for our original charter date didn't work out, he was extremely proactive in reaching out and getting ti rescheduled asap. On the day of the charter itself, the whole experience was seamless and the group had a fantastic time. They would definitely do it again!

  6. Josh

    Josh

    7 to 13 passenger Lake Michigan Sailing Charter

    My friends and I have chartered a few boats here in Chicago, but this was by far the best experience we have had. We actually had to reschedule our initial cruise last minute due to bad weather. The boat owner, Russel, was very communicative and made the best of the not-so-great situation. He graciously offered to allow for our group to enjoy the boat for a lesser amount of time and stay at the dock. We were also able to reschedule for the following week and go out with Captain Brian at that time. Our group had such an amazing time during both sessions. We certainly had some strong personalities in the bunch (myself included) and Captain Brian was such a great sport. He was very professional but also blended in so well with our group that he was like another guest. We will without a doubt be reaching out to Russel & Captain Brian again for future events. Thank you both for making this such an unforgettable experience for us and our guests.