The Best Sailboat Rentals Near Old Hickory Lake

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

Nijole was an incredible host/communicator. They made the booking and the trip easy, care-free and relaxing. The boat, The Harmony, was beautiful and clean. My fanily and I had an incredible experience and are excited to book another excursion soon!

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

I was impressed that everything went according to plan. Met Captain Bob right on time and boarded what looked like an almost brand new boat. Very well maintained and extremely clean. First mate was first of all and offered water and refreshments for myself and my guest. Leaving the marina was professional and uneventful. The wind was light and variable and made for rather slow sailing but it was a great opportunity to hear some of the fine stories connected to Helios. For anyone that wants a true sailing experience and an opportunity to talk to some people that have been there done that, charter this sailboat! Thank you Captain, maybe we can have another adventure later in the summer.

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

We had a last minute booking and Nicole was kind enough to accommodate us and communication was great. Amazing boat, super friendly couple who are great to have conversations with. They made sure everyone had a great time safely. Highly recommend!

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

This was 1000% the way to go for boat rental! Derrick was absolutely incredible. We found him through a Gemini AI search and we couldn’t be happier! The boat was well maintained and came with everything we needed including complementary gas and tubes so we could just enjoy our time on the lake! He was so flexible with drop off and pick up and made the experience so relational and positive for our family!

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

Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!