About Us

Company History

Fairwind Sail Charters, Inc. is one of Chicago’s oldest and most respected sailing businesses, founded in 1978. Fairwind began as a sailing school, soon gaining a reputation for top-quality education geared especially toward sailors wanting to sail larger cruising yachts. In the early 1980s, Fairwind pioneered the idea of time-sharing sailing yachts. Under Fairwind’s unique Sailing Yacht Lease Share program, sailors were able to share the use of a sailing yacht with other sailors for a fraction of the cost of short-term rental or ownership.

Fairwind’s idea of making sailing yachts accessible to sailors who lack the time or resources to own their own boat has been copied by many imitators in ensuing years, but Fairwind has maintained its leadership role in the Chicago marine community by offering great boats, professionally maintained and cared for by a hands-on owner/operator, in an excellent location and at a remarkable value. Capt. Ben Sells took over the helm at Fairwind in 1998.

Owner’s Profile

Captain Ben Sells of Fairwind Sail

Capt. Sells brings an exceptional background to his leadership at Fairwind. He is a retired attorney and psychotherapist who now splits his time between writing, running Fairwind Sail Charters, and being President of the Village of Riverside. After leaving law practice in 1991, Capt. Sells opened a psychotherapy practice in Chicago and began writing a nationally syndicated column on psychological issues in professional life. His columns developed a large and enthusiastic audience, and this aspect of his work culminated in three books on law and psychology, The Soul of the Law, and Order in the Court: Crafting a More Just World in Lawless Times, and The Essentials of Style: A Handbook on Seeing and Being Seen. He also edited Working with Images: The Theoretical Base of Archetypal Psychology, an anthology on the theory and practice of archetypal psychology. Capt. Sells is widely sought as a teacher and lecturer on psychological theory and practice and their implications in current cultural affairs. His “America Tapes,” with famed psychologist James Hillman, won him a Gradiva Award from the National Association for the Advancement of Psychoanalysis, and he is a repeat lecturer at the prestigious Eranos Roundtable in Ascona, SZ. His latest books focus on Chicago history: The Tunnel under the Lake: The Engineering Marvel that Saved Chicago, was released in 2018, and A History of the Chicago Portage: The Crossroads That Made Chicago and Helped Make America, was released in 2021.

In spring and summer, though, Capt. Sells is all sailing. He holds a 100 Ton Master’s License from the U.S.C.G. with Sailing and Towing Endorsements and is an American Sailing Association certified sailing instructor through Advanced Coastal Navigation. As the owner/operator of Fairwind, he personally oversees all aspects of its operation, from the daily maintenance of the Dragon Fleet to his duties as Senior Instructor in Fairwind’s sailing school. Under Capt. Sells’s leadership, Fairwind became Chicago’s first sailing training facility to be certified by the American Sailing Association, and ASA awarded Capt. Sells their prestigious Outstanding Instructor of the Year Award, an award based on evaluations provided to ASA by Fairwind’s students. A popular and highly experienced teacher, Capt. Sells is known for his good humor, easy manner, and meticulous seamanship.

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.

Fairwind Sailing School

ASA American Sailing Association Logo

For folks new to sailing, Fairwind offers ASA’s Basic Keelboat Sailing (101) and Basic Coastal Cruising (103) Certifications, which take students from basic sailing skills through how to handle a mid-sized sailing yacht under power. For more advanced sailors, Fairwind offers ASA’s Bareboat Charter (104) Certification for those who plan to charter boats in the islands or who perhaps hope to own their own boat someday.

Fairwind also offers ASA’s Advanced Coastal Navigation (105) Certification for sailors who want to increase their navigation skills. After completing their instruction, many students take advantage of Fairwind’s Sailing Yacht Lease Share Program to gain valuable experience at an economical cost.

Fairwind Sailing Yacht Lease Share Program

Fairwind’s innovative Sailing Yacht Lease share program gives sailors scheduled use of a sailing yacht for an entire sailing season from mid-May through mid-October. Fairwind provides all related services including commercial-grade insurance, daily maintenance, cleaning, fueling, pump-outs, storage, etc.

Fairwind’s great boats, unbeatable location, professional management, and excellent value are why so many sailors stay with Fairwind for years. Since Capt. Sells took the helm in 1998, Fairwind’s Sailing Yacht Lease Share Program has had an annual customer renewal rate in excess of 90% and consistently leads all competitors in customer service and satisfaction.

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.

Fairwind Private Sailing Charters

Whether for a quiet afternoon sail, a corporate outing, an exciting fireworks sail, or one of Chicago’s many summer special events Fairwind offers private charters for up to six passengers with highly skilled, licensed captains.

The Dragon Fleet

Dragon Fleet

Fairwind’s Dragon Fleet currently includes: Chidragon, a Beneteau 40; Dragonfly, a Beneteau 38; Silver Dragon, a Beneteau 37; and Flying Dragon, a Beneteau 373. The Dragon Fleet is docked in 50-foot, walk-on slips in the northwest corner of Burnham Park Harbor at the heart of Chicago’s Museum Campus. Fairwind’s customers love the safety and convenience of walk-on access (no dinghies or tenders to deal with), and the ample close-by parking.

With 46 years of commitment to Chicago’s sailing community, Fairwind looks forward to many more sunny days, confident students, happy charters, and the warm, cooperative family of skippers that make Fairwind an oasis for Chicago sailors. Capt. Sells calls Fairwind’s little corner of paradise “Key Midwest,” and invites sailors to become part of Fairwind’s future course.

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.