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Embark on a Memorable 
Sailing Experience

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. With Dorothy Cunningham as your skipper, you will be safe, you will have fun, and you will learn! 

A Unique Adventure

Challenge Sailing School offers a unique and exciting adventure on the water that is both fun and educational.


Discover the thrill of the open sea

Whether you're a seasoned sailor or just starting out, Challenge Sailing School provides an opportunity to escape.

What are people saying

What a tranformative week!  

Thank you for your efforts & perseverance in making our family week so special!

Andrew & Janet M

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