Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

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. vp

   vadim

   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!

6. SB

   Susan

   May M-F Special! 8-13ppl Bareboat Rent 3hrs Get 4th hr 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!