The Best Sailboat Rentals Near Osage Beach

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

This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

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!

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.

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!