Great sailboat rentals near Chicago, Illinois.

Sailing Reviews in Chicago

1. M

   Mark

   Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. 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.

2. DV

   Danielle

   Sail & Swim from a Luxury Sailing Yacht

   We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

3. S

   Sandra

   Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. 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.

4. J

   Jeff

   Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. 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.

5. hf

   hunter

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Excellent captain with a wonderful boat and personality. Highly recommend for lovers of sailing.

6. LT

   Leslie

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

   if you ever book, you must use these guys. i cant swim and they made me feel very secure