Fairwind Sail Charters

I have been sailing with Fairwind for twenty years, ever since getting hooked on sailing during a Caribbean bareboat adventure. Fairwind has been the most convenient and economical way to satisfy my craving. There have been countless times I wanted to buy my own boat, but I always return to reality and realize that for people like me with lots of other family and career commitments, timesharing gives me sailing without all the hassles of ownership. Capt. Ben tends Fairwind like an extended family. He is always available for a friendly chat or some sailing advice. Most importantly, his boats are in top condition and always cleaned up and ready for the next timeshare turn.
Gary G.

When you sail with Fairwind you know you’re among people who live and breathe sailing. The owner and head instructor, Captain Ben Sells, has what I have always thought of as archetypal “sailor-like” traits: forethought, a preference for order, composure, flexibility, resourcefulness, resilience and wisdom. And it is evident that all of the Fairwind boats are maintained with the same meticulous care and love that a true sailor would lavish on the vessel that carries him safely from adventure to adventure. Even though I have spent countless summer days on the edge of Lake Michigan enjoying the many shopping and dining pleasures that Chicago has to offer, nothing compares to the exhilaration of a sunset sail on the lake. Seeing the Chicago skyline from the water, with the sun setting behind the towering buildings…this is definitely an experience not to be missed.
Mandy C.

Capt. Ben of Fairwind is dedicated to making the sailing experience safe and enjoyable. The boats are well maintained, clean and easy to handle. It is a much easier and less costly way to go for the casual sailor. It is among the best deals in sailing around.
John L.

I look forward to our sixth season of time sharing with Fairwind. It is great to have sailing times that you just have to accommodate out of your busy schedule, to do what you enjoy and to bring friends and business colleagues with you for a lovely time on the water - especially on Weekday afternoons! The lack of responsibility for the boat other than during the time you have it is wonderful - Ben takes great care of the boat and all that goes with it.
John C.

I took sailing lessons and then realized I had no way to put what I learned to use. The Fairwind Sailing Yacht Timeshare Program was exactly what I was looking for. It gave me access to a boat without the cost and hassles of boat ownership.
Joe U.

After some rather discouraging experiences with other organizations, it was wonderful to find Fairwind. Simply put, Fairwind’s perfect upkeep and management of their fleet leaves the sailor free to worry only about how deeply they can appreciate their sailing experience.
Dave A.

There are few people - myself included - who have the time to own a sailboat. My wife and I don't want to spend what spare time we do have maintaining a boat and we have enough other interests that we don't want to spend every spare moment in the summer on a sailboat. Fairwind is the perfect solution - we step on a boat clean, rigged and ready to sail and go sailing. No worries about winterizing - no worries about maintenance - and no guilty conscience because we aren't fully using our very expensive asset.
Pat P.