About Dorothy

Your host and skipper, Dorothy Cunningham, quite simply,  loves sailing. 

Growing up on the Great Lakes, Dorothy spent a lifetime enjoying any endeavour which had the basic requirement of getting on or in the water.

Scuba diving was the bond that introduced her to her husband, Philip, 37 years ago.

Vacations were spent swimming, diving, snorkelling, canoeing and sailing.

Together they dreamed of one day living on an Island and owning a Sailboat and set out to make that goal a reality. 

After 22 years of building, managing, and owning a successful Real Estate brokerage, Challenge Realty, Dorothy started a sailing school and of course, called it Challenge Sailing School!

Dorothy's passion for sailing has taken her sailing across the Atlantic Ocean, crewing on the Vic Maui race from Victoria to Hawaii and delivering the vessel back to Canada. Various sailing trips have seen Dorothy sail from the very southern tip of Mexico to the very Northern tip of the British Columbia coast - the experience of saiing through Haida G'Waii alone leaves magical memories for a life time!

Local races around Salt Spring and Bowen Island have provided wonderful experiences for all of the crew members who signed on for an It's Magic adventure. 

Dorothy has  been able to apply her business experience as a coach, manager and trainer to the Sailing world - she is a  certified Sail Canada instructor as well as a certified American Sailing Association Instructor.

It is absolutely certain that if you step on board It's Magic,

You'll be safe

You'll have fun.

You'll learn..