The Best Sailboat Rentals Near Whittington

Private Cruise Onboard 32ft Hunter Legend Sailboat in Chicago

I am new to the world of sailing, and this was an awesome experience. I was able to have hands-on learning about sailing in the midst of a safe environment and a competent captain. As I don’t own, my own boat, the cost was very reasonable. I plan to do this again then near future!

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

The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

Ted was the captain of the boat and was excellent. He made our ride very enjoyable and stayed out for the fireworks at the end which was amazing. Kids loved the experience too!

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

Patrik did a great job getting us out on the water. There was a storm coming in and we had to cut the sail a little short but the winds did not disappoint. Great tour of the harbor and the city skyline. Patrik let us take the helm and experience sailing on the lake. Wish we had more time but better to be safe and dry.

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

What a Wonderful evening we had on the water with Nijole, her 1st mat (hubby) and precious little Piper "the pup". This sail boat is a MUST BOOK! Nijole's sailing abilities, great stories and knowledge of the water on and surrounding Lake Michigan are exemplar! We had such an incredible majestic peaceful evening on the water! Will be back on the HARMONY next Chicago Visit for Sure. Carrie, Kelly, Mike & Zac ( Naples, FL) :0)

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.