Company History

Fairwind Sail Charters, Inc. is one of Chicago's oldest and most respected sailing businesses, founded in 1978 by  Capt. Denise McNamara.  A legend in Chicago sailing circles, Capt. McNamara was one of the first women officers in the Merchant Marines, holds an Ocean Master's rating from the U.S.C.G., is an avid racer (winning her class in the prestigious Chicago-to-Mackinac Race, as well as numerous Boat of the Year Awards), and a cruising sailor with worldwide experience. 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, Capt. McNamara 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. 

Capt. McNamara'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. In the mid-1980's, Capt. McNamara taught a young lawyer to sail.  After completing his sailing lessons, he became a time share skipper in Fairwind's Sailing Yacht Lease Share Program.  Over a decade later, in 1998, having sailed with Fairwind as a time share skipper for that entire time, this same sailor, Capt. Ben Sells, became Fairwind’s new owner.

Owner's Profile

Like Capt. McNamara before him, Capt. Sells brings an exceptional background to his leadership at Fairwind's helm.  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 two books on law and psychology, The Soul of the Law, and Order in the Court: Crafting a More Just World in Lawless Times.  He also has served as editor for two anthologies on the theory and practice of archetypal psychology, and 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 book, The Essentials of Style: A Handbook for Seeing and Being Seen, has just been released.

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 a certified training facility with American Sailing Association, the only such school in Illinois, and in 2002 Capt. Sells was awarded ASA's 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. 

Fairwind Sailing School

For those just starting out, Fairwind's Cruising Sailing I course combines ASA's Basic Keelboat Sailing and Basic Coastal Cruising Certifications to take the student from basic sailing skills through how to handle a mid-sized sailing yacht under power.  For the more advanced sailor, Fairwind's Cruising Sailing II course provides ASA Bareboat Charter 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 Certification for sailors who want to increase their navigation skills. Fairwind is the only Chicago sailing school to teach on cruising yachts. After completing their instruction, many students take advantage of Fairwind’s Sailing Yacht Lease Share Program to gain valuable experience at an economical cost. And Fairwind is always available for help and advice.

Fairwind Sailing Yacht Lease Share Program

Our innovative time share program gives sailors scheduled use of a sailing yacht for an entire sailing season. Although called a time share, sailors actually lease time on Fairwind’s boats – there is no transfer of equity and no risk of ownership to the time share skippers. About ten sailors share each of the sailing yachts in Fairwind’s fleet. The two basic sailing schedules are ten sails or twenty sails spread evenly over the sailing season of mid-May through October 15. 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 of 90%.

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 

Fairwind's Dragon Fleet currently includes: Chidragon, a 2008 Beneteau 40; Dragonfly, a 2009 Beneteau 37; Flying  Dragon, a 2006 Beneteau 373; Snapdragon, a 2006 Beneteau 373; and Blue Dragon, a 2007 Beneteau 343. 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 its 30+ years of commitment to Chicago's sailing community, Fairwind looks forward to another 30 years of sunny days, confident students, happy charters, and the warm, co-operative family of time share skippers that make Fairwind a oasis for Chicago sailors. Capt. Sells likes to call Fairwind's little corner of paradise Key Midwest, and is ready to welcome sailors to become part of Fairwind's future.