Incredible sailboat rentals in Illinois, United States.

Sailing Reviews in Illinois

1. MJ

   Meneka

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

   Sailing with Nijole and her husband was an incredible experience! From the start, they were very responsive in communication and flexible with our requested times, even allowing us to extend once on the water. Their knowledge, warmth, and passion for sailing made the trip both safe and fun, with stunning views that we’ll never forget. Highly recommend!

2. ZD

   Zinnia

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

   Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!

3. KM

   Kasey

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

   I booked this experience because Nijole had amazing reviews — and now I truly know why. She is talented, no-nonsense host who knows exactly how to make you feel comfortable when you're aboard. We could not have been more grateful or had a better time. Thank you, Nijole! A superstar.

4. 

   Federica

   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 !

5. SB

   Susan

   38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!

   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!

6. MD

   Morgan

   38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!

   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!