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. SN

   Sergey

   Private Cruise onboard Hunter Legend Sailboat in Chicago

   We (myself and 5 of my friends) had a private boat tour with Captain Mitch, and it was a greta experience. We did plenty of swimming in the open lake (outside the harbor) and did a quick tour along the shoreline. Mitch is very knowledgeable about the lake and the city, and many other things - it was both entertaining and educational to chat with him. Highly recommend!

3. SB

   Sean

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

   Excellent experience all around. Our excursion was a great mix of swimming and peaceful cruising under sail. Nijole was a great captain and created a wonderful experience for a family afternoon on the water.

4. SG

   Stephanie

   Special End of Season Sunday pricing for 8 to 13 passengers

   My friends and I rented Captain Russell’s boat for a wedding weekend celebration and had the best time! The boat was beautiful, and Captain Brian made the whole experience super enjoyable. Highly recommend!

5. JM

   Julie

   No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

   Great vessel. Everything we needed! Amazing deck hand and Captain (Georgia and Matt). They made our air and water show experience incredible!

6. NB

   Nicole

   20ft Bayliner VR5 Boat in Rockville, IN

   First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!