Instruction in Parry Sound
Instruction in Parry Sound
On Georgian Bay!
Instruction in Parry Sound
Instruction in Parry Sound
On Georgian Bay!

Covid 19 Update - January 2021

Diamond Waters Sailing will continue to offer our complete range of courses in 2021. We respect the Covid 19 guidelines and apply them to best minimize risk. Blue Pearl is sanitized between groups. Courses will be offered to families and close social bubbles, by reservation. Contact us at We might not all be in the same boat, but we are all in the same C – as in sea or corona virus. Stay safe and we’ll be sailing together soon.


Our vision is for Parry Sound to be a global cruising destination where sailors experience the finest fresh water sailing in the world and are warmly welcomed by the community with its diverse local culture.


Our mission is to share our skills and knowledge with people who want to learn to sail and improve their boating skill, to demonstrate good environmental stewardship and to promote strong community partnerships.


We value healthy active living, nature’s beautiful natural resource and the rich cultural history of Georgian Bay.

About Us


Diamond Waters Sailing offers family friendly keelboat sailing and cruising instruction on the beautiful waters of Parry Sound, among the 30,000 islands of the Georgian Bay Biosphere. We are Sail Canada certified instructors and sail Blue Pearl, an LM30, safe and comfortable cruising yacht, registered with Sail Canada and Transport Canada as a Recreational Boating School.






WHat people think about our trips & courses

I got hooked on keelboat sailing thanks to Diamond Waters Sailing instructor Larry Woolner – beginning with the Discover Cruising course, then Start Keelboat Sailing and now my most recent accomplishment, the Basic Cruising Course. Prior to taking these courses with Larry, my sailing experience had been limited to dinghies, and very patchy at best. I knew just enough to know that this would be a meaty challenge, and that in order to be successful I’d need an instructor who would be patient, supportive and knew how to break down the more complex, technical aspects of sailing. Larry, who is a mechanical engineer, was all that – and more: his ‘secret sauce’ is his infectious passion for sailing and his enthusiasm for his students. Thanks to Larry and Diamond Waters Sailing, I can now competently “head up” and “bear away” when at the helm; I can “ease” and “harden” sheets as crew; I am learning to read the wind, water and clouds… If you’re thinking about learning to sail a keelboat I highly recommend Larry Woolner’s Diamond Waters Sailing – and there’s no better place to do it than on beautiful Georgian Bay. Fair winds!

In the summer of 2019, I took the “Discover Cruising” followed by the “Basic Cruising” sailing courses with Larry Woolner from Diamond Waters. The ‘Discover Cruising” course helped me to review many of my points of sail and basic sailing skills that I had learned in sailing school. This first step made me very enthusiastic to continue to master the more detailed aspects of this wonderful sport and to eagerly spend three full days in obtaining the “Basic Cruising’ standard. I can honestly say that those two courses were among the best experiences I have ever had from an educational standpoint. Larry has exceptional capabilities with his ability to keep his students engaged and focused. His method of instruction helped me to retain even the more complicated information and made it easier for me to put theory into practice. Larry was very patient with all of us on the boat as we practiced our sailing skills on the beautiful shores of Georgian Bay. His friendly nature made us feel very welcome on his beautiful yacht, the Blue Pearl. I would highly recommend Larry Woolner to anyone who would like to spend the day on the beautiful waters of Georgian Bay learning to sail.

As an experienced sailor I took the opportunity this summer to challenge the Sail Canada Basic Cruising course with Larry Woolner of Diamond Waters Sailing. It was a fabulous 3-day course of both practical and theoretical instruction on the beautiful waters of Georgian Bay. Larry is a dedicated and passionate instructor and made the whole experience very memorable. He is very talented in his ability to deliver lesson plans and in helping his students put theory into practice. For any seasoned sailor looking to refresh their theoretical knowledge and improve their sailing techniques, I would highly recommend Diamond Waters.

We just completed the four day Basic Cruising Standard with Larry aboard Blue Pearl. Diamond Waters is the perfect venue to gain confidence on a majestic sailboat with a patient, details-oriented instructor. Clearly, Larry’s life as a professional engineer and sailor combine to raise the skills of the entry level sailor to crew on the world class waters of Georgian Bay. I highly recommend this course to anyone wishing to set sail on Georgian Bay or anywhere else in the world.


Diamond Waters Sailing cruises into Parry Sound’s fall. 

After being docked by COVID-19, Parry Sound keelboat sailing and cruising instruction company Diamond Waters Sailing launched in August.