Sailing Instructor Spotlight ::: Jim Stewart

Sailing Instructors are the backbone of any good sailing program and we are very proud of ours. For years and years our sailing schools and their instructors have been chalking up awards and more importantly, praise from our Members! From time to time we will feature our instructors to help you get to know them better.

As one of the first sailing bases to operate in our franchise system, SailTime Chicago was started in 2005 and Jim Stewart joined our base there in its first year of operation as the Manager of Training Operations. A few years later, SailTime Milwaukee was opened in 2009 and Jim has lent his guidance, coordinating the American Sailing Association (ASA) Sailing School for us there, since then. Subsequently, SailTime Milwaukee was recognized in 2009 & 2012 as an ASA Outstanding Sailing School of the Year!  ASA has also awarded Jim their Outstanding Instructor Award for 2009, 2013 and again, last year.

Captain jim never misses a teaching moment!
Captain jim never misses a teaching moment!

Jim and his wife, Jane, both retired from the real world at the turn of the century. He got his Coast Guard Captains License in 2003 and started teaching people to sail in 2004. He feels his work with IBM and The US Navy, which involved extensive teaching experience contributed to his teaching abilities. Seeing as how the ASA awards come directly from student feedback, teaching is a richly rewarding experience for him.

Jim sailed small boats in Minnesota as a youngster and by the 1980’s, sailing had become a full blown obsession! Lucky for him, Jane enjoys water sports and sailing too. “She got me into scuba diving and i got her into sailing,” Jim said. Love. Match. They’ve been cruising the Great Lakes and living aboard on their Sabre 38 at Racine, WI since 1998. The wilderness of the Ontario shore, Lake Superior and the scenic beauty of the North Channel, Lake Huron, top their list of favorite cruising grounds. Cruising the Lakes, plus their charter adventures, keeps them on the water most of the year.

Jim says, “Many of my students are looking for skills and confidence that will enable them to charter a sailboat as a vacation activity.” SailTime helps keep these sailors competent and involved in the sport in their home waters, so they can fully enjoy chartering in exotic destinations. Jim and Jane have done extensive chartering too as well as planning and leading group trips. Memorable sailing destinations include the San Juan Islands of the Pacific Northwest, from Key West to the Dry Tortugas, the Spanish Virgin Islands and of course, the BVI.

Jane is more than an enthusiastic partner in Jim’s sailing activities. She conducts boat safety inspections as part of the Coast Guard Auxiliary’s Program. Jim concludes, “We jointly do a cruise planning course through our local Racine Sail and Power Squadron boating club.”

Members and Boat Owners in Racine, Milwaukee and Chicago are lucky to have someone that is not only qualified to teach, but has a real passion for it and the attitude to be a great instructor. He teaches everything from Basic Keel Boat (101) all the way up to and including Advanced Coastal Cruising (106) as well as Cruising Catamaran and Docking Endorsements. Suffice to say, our Members in the midwest are some of the best trained sailors anywhere!


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