Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

1. LS

   LizSeptember, 2023

   46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!

   Everything with our rental was perfect. Nasco was very responsive with our booking and any questions we had. He also helped by providing several captain recommendations. The boat itself was perfect for our group of 12. We had plenty of room to sit, move around and the lily pad was great for those of us wanting to go into the water. We will definitly use this boat in the future and recommend it to anyone else looking for a Boat in Chicago!

2. vp

   vadimSeptember, 2023

   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!

3. RJ

   RobertAugust, 2023

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.

4. JL

   JohnAugust, 2023

   Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

   Had a great outing on a windy day, learning the details of the boat and watching the beautiful Chicago skyline from the best vantage point around. Ben was a great captain and provided a great sense of confidence and enthusiasm.

5. NC

   NatalyAugust, 2023

   46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!

   Nasco was very communicative and reliable and even recommended a reliable and great list of captains to hire. The boat was clean and exactly as shown in the pictures and as described. We had a great time with the boat! Would definitely recommend to other friends.

6. HR

   HannaAugust, 2023

   46' Spacious Portofino Party Yacht For Every Occasion

   I chartered Captain Kyle's boat for my birthday with 12 of my friends and it was a great experience! Communication was top notch and they accommodated a new date when our original date was rained out. Captain Dan was super nice and very professional. The only constructive criticism is that the boat is a long walk from any parking/drop off point at the harbor so be prepared to carry your coolers and belongings a ways. Also, the boat is dated so cushions/surfaces could use some TLC. Also, be sure to bring your floaties or a lily pad because the boat has neither. Overall this is a great boat for the value and I would book again!