Cookies & Agreements

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.

All listings in Lake Michigan

Awesome cruising catamaran rentals in Lake Michigan, United States.

Page 1 of 13 listings

Special End of Season Sunday pricing for 8 to 13 passengers
Sailing in Chicago · 13 guests

Special End of Season Sunday pricing for 8 to 13 passengers

5.0
$550/hour
Ask about our SPECIAL end of season Sunday Savings! Captain included.
Sailing in Chicago · 6 guests

Ask about our SPECIAL end of season Sunday Savings! Captain included.

5.0
$450/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Best of 2025
$375+/hour

Cruising Catamaran Reviews in Lake Michigan

  1. SB

    Susan

    Special End of Season Sunday pricing for 8 to 13 passengers

    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!

  2. MD

    Morgan

    Special End of Season Sunday pricing for 8 to 13 passengers

    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!

  3. M

    Mark

    Ask about our SPECIAL end of season Sunday Savings! 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.

  4. S

    Sandra

    Ask about our SPECIAL end of season Sunday Savings! 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.

  5. J

    Jeff

    Ask about our SPECIAL end of season Sunday Savings! 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.

  6. SD

    Shaunak

    Chicago's Largest Chartered Catamaran!

    Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!