about Diamond Waters Sailing

Sailing for a healthy planet

Diamond Waters Sailing has been formed to help adults and families discover nature’s wonders and their potential while experiencing the finest freshwater sailing in the world. The 30,000 islands of the Georgian Bay Biosphere (GBB) make Parry Sound a spectacular cruising venue, attracting sailors from everywhere.

Diamond Waters Sailing is a Transport Canada registered Recreational Boating School with Sail Canada Certified instructors. No boating experience is required to safely and comfortably learn to cruise. All day sailing adventures are in light to moderate conditions. While underway, guests receive instruction to crew the vessel with a focus on safe boating and keelboat handling to Sail Canada training standards. Skills are developed in a progressive skill building program from beginner to competent crew and skipper. Guests must be physically able to move around a boat underway and handle lines with moderate strength.


Larry Woolner, P.Eng. 

I moved to Parry Sound from Kitchener in 1987 to start my engineering career with a global manufacturing company. It was my love of canoe camping, my longing to sail and  the beauty of the Bay and lakes that drew me to Parry Sound as much as my work. The welcoming, supportive community and rich, diverse culture convinced me to stay. I’m a proud father and grandfather, professional machine head, active volunteer and my passion for healthy, low impact living increases every time I am outdoors…

  • Sail Canada Cruising Instructor: Basic Cruising, Coastal Navigation, 2018 – present
  • CCGA Search And Rescue Instructor, 2019 – present
  • SVOP MED3, 2017
  • American Boat and Yacht Council (ABYC) Master Marine Technician, 2014
  • Canadian Coast Guard Auxiliary Parry Sound Unit Search And Rescue technician, 2011
  • Canadore College GPS Instructor, Canadian Ecology Center certified, 2005-2011
  • Sail Canada Dinghy Instructor, 2005
  • Sail Parry Sound VP Operations. Founding member in 1998 and Commodore from 2007-2014.
  • Canadian Power and Sail Squadron JN. Studied and instructed safe boating in Parry Sound since 1988. Commander of the CPSS Parry Sound unit 1995-1996.

Sue Pilling

It seems like my life always leads me back to sailing – that’s a good thing I’m finding. My father was an avid sailor and boat builder. He built a small Mirror dinghy when I was ten so he could share his passion and spend more time with his two girls. That decision was the rudder that steered my life and I quickly grew to share his passion and competitive spirit. Growing up sailing gave us great friendships that have lasted for years. Through summer jobs teaching youth dinghy, disabled sailing in Vancouver, cruising around the South Pacific, and teaching adult live-aboard Cruise and Learns,  I’ve learned that I enjoy passing my knowledge on to others – and I always learn a lot from everyone too. To continue to grow the sport in my community with Sail Parry Sound and beyond, Larry and I have started this new adventure. We look forward to meeting you!

  • Sail Canada Cruising Instructor: Basic, Intermediate, Advanced Cruising, Coastal Navigation Instructor, PCOC Program Instructor 1998-present
  • Sail Parry Sound Board Member and Regatta Director, 2015-present
  • Accomplished Dinghy Racing (Top Female Helm 2013, 2016 Wayfarer World Championships)
  • Founding Member Blue Sky Sailing Club, North Bay, ON 2006-2010
  • Sail Canada Offshore Cruising Standard, 2005
  • Disabled Sailing Association of BC Instructor, 1990-1996
  • Sail Canada Dinghy Instructor Red Level, 1981-1992

OUR Partners

Click to view each website.


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.


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.