Jim Stewart - Outstanding ASA Instructor

It’s a Wonderful Life!

By: Instructors

According to criteria and judgment of the American Sailing Association, Jim Stewart is a model sailing instructor. He has now been recognized as one of ASA’s Outstanding Instructors for the third time – 2009, 2013 & 2014. He and his wife Jane retired from the “real world” in 2001 and he started teaching sailing as a livelihood in 2004. Apparently he is quite good at it.

A lot of folks feel I have the perfect retirement job,” Stewart says. “As I tell my students when we are enjoying a great day on the water ‘Sure you guys are having fun, but this is just another hard day at the office for me…’ That always gets a lot of groans.

Stewart may joke that he’s got it easy but he has earned this Outstanding Instructor award during his time teaching at SailTime Milwaukee. Beyond all the positive feedback he’s received from his students, he has worked hard all along the way completing ASA instructor qualification levels: 101, 103, 104, 105, 106, 114, and 118. He knows his way around a sailboat. And this knowledge is put to purpose beyond his teaching day job. Jim and Jane love to put their skills to the test and charter in interesting and exotic places. He understands that many students are looking to have the ability to do the same, so hands on chartering experience is something he looks to have and pass on.

Many of my students are looking for the skills and confidence that will enable them to charter a sailboat as a vacation activity,” Stewart says. “Jane and I have done extensive chartering around the US, Canada, Mexico and the Caribbean.

The couple has planned, organized and led many charter trips. In the recent past they’ve sailed Key West to the Dry Tortugas on a 47ft cat, did a winter trip to the BVIs, a fall trip to the San Juan Islands and most recently chartered in the Spanish Virgin Islands.

If all that sailing and teaching isn’t enough, Stewart also published a book, “Boat Handling and Docking”. Now there’s a guy who has turned his passion into a fun living.