top of page

Take the Challenge for Fun, Adventure and Learning with Challenge Sailing School!

Challenge Sailing School is your perfect choice for an adventure on the water or certification leading to future adventures on the water, including Chartering in the Mediterranean. 

With Dorothy Cunningham as your skipper, you will be Safe, you will have Fun, and you will Learn!


Sailing with Peace of Mind

Dorothy is a certified Sail Canada, American Sailing Association and International Yacht Training Instructor with experience in offshore passages, racing and teaching sailing.

It’s Magic, our 40’ training vessel is a Transport Canada Recreational Boating School approved sailing vessel and is a comfortable “racer / cruiser” with 3 cabins and a spacious saloon.

Building skills, building confidence, building memories

We offer Sail Canada and International Yacht Training (ICC certification) courses and certification, vacation packages to build mileage and confidence and Women On Water courses. We also offer docking and anchoring clinics throughout the year.


Whether you’re a beginner or an experienced sailor, Dorothy will provide you with the skills you need to navigate the waters while having fun safely and confidently.  Join Dorothy and set sail on an adventure of a lifetime with Challenge Sailing School.

bottom of page