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
  • Canadian Coast Guard Auxiliary (CCGA) Search And Rescue, Parry Sound Unit Leader – 2021, Technician – 2011 
  • CCGA Search And Rescue Instructor, 2019 – present
  • SVOP MED3, 2017
  • American Boat and Yacht Council (ABYC) Master Marine Technician, 2014
  • 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

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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 local community with its diverse cultural heritage.


Our mission is to share our skills and knowledge with people who want to learn to sail and improve their boating skill, to provide sustainable social, economic, cultural and environmental benefits, and to promote strong community partnerships.


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


WHat people think about our trips & courses