The Best Sailboat Rentals Near Whittington

20ft Bayliner VR5 Boat in Rockville, IN

First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!

Set Sail with 36' Sailing Boat in Downtown, Chicago

Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.