Marine News from the Great Lakes

Our Journey Of The Heart

Published: Monday, July 29, 2019
By: Cindy Kalow

What happens when you mix your sailing hobby with your occupation? Then, throw in working with your spouse, and you have created a reason for many hours of therapy! It has been 15 years since we took those first steps and began what we like to call our ‘journey of the heart.’

Back then, my husband and I were looking for another hobby our family could enjoy together and a skill to teach our children that would be something they could enjoy throughout their life. Our neighbors introduced us to sailing larger boats and we quickly signed up for a bareboat sailing course from a family-owned company called Superior Charters, located in Bayfield, Wisc. Bayfield is a small, picturesque town known as ‘the gateway to the Apostle Islands.’ We were not only smitten with sailing, but quickly became addicted to this small community perched on the edge of Lake Superior.

The next three years found us chartering once a month throughout each summer. Our desire to sail pushed us to boat shows where our efforts to shop for a boat were soon rewarded with the purchase of an older, but well maintained, 47’ Valiant. We arranged for trucking from the Chesapeake Bay to a new marina in Bayfield, and then enjoyed sailing her, exploring the Apostle Islands and into other ports on Lake Superior.

I can still remember the day my husband excitedly came down the companionway of our boat and disrupted my peaceful reading of a book with the news that the charter company was for sale and we should buy it! The idea quickly took a life of its own and, after many months of negotiating and life planning, our family changed the trajectory of our suburban life. We had always intended to take an extended trip on our sailboat, to give our children the taste of a different lifestyle. Instead, we gave them a taste of small-town living, growing up running a family business, living on the shores of one of the most beautiful lakes in North America. Today, our journey of the heart continues. Our boys have become sailboat racers. My oldest works in the business with us full time and we continue to introduce sailors to this magical cruising grounds, The Apostle Islands.

Like many families, boating is what we do to relax and dissipate some of the stresses of life. You are welcome to be part of our family at


This article first appeared in the Summer Issue (Jul/Aug) 2019 of Great Lakes Scuttlebutt magazine.

tags: Charters, Lake Superior

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