Penny Caldwell


My name is Penny Caldwell and I am a Cruising Instructor with Sail Canada. I am 37 years old and began teaching for Sail Canada in 1995 at Harbour West Sailing Adventures in Hamilton. My hometown is actually Pointe-Claire in Montreal, but I did most of my sailing on the Great Lakes and Georgian Bay.
Fun fact: Hamilton is dubbed the “Waterfall Capital of the World” as they have over 100 waterfalls within the city limits which cascade down the Niagara Escarpment. The Niagara Escarpment is a UN World Biosphere Reserve, as it is an ecosystem with plants and animals of unusual scientific and natural interest.

Are you affiliated to a club/school? If so which one?

I am the founder and owner of Sail Nelson, which is located in the picturesque mountain town of Nelson BC in the Central Kootenays. We relocated our family here from Ottawa 3 years ago when we wanted a better family life. There was no sailing school here, so in 2017, I started one! Nelson’s population is about 10,000, however it more than doubles in the summers when tourists come to play in the mountains or on Kootenay Lake. Nelson is also a huge ski town and the local hill, Whitewater Ski Resort, is often bustling with European tourists in the winter. Fun fact: Kootenay Lake is one of the largest lakes in British Columbia, at 104 km in length and 3–5 km in width and the average depth is 148 ft (yikes!).

What certification levels do you have?

I currently hold a Basic Cruising instructor certification, however I used to be an Advanced Cruising instructor when I taught for Harbour West (Hamilton) and the Ottawa Sailing School (Adventure Boating). I spent most of my cruising time in Georgian Bay and a few years in the Thousand Islands out of Kingston. I also taught some Basic Cruising courses for the Pointe Claire Yacht Club in Montreal and started up their French cruising program in the late 90s.  I have a bio on my website here 

How long have you been an instructor/official?

I have been teaching for Sail Canada (CYA) since 1995. I did take several years off after I had kids to focus on family, however now that they are older and sailors themselves it just made sense to start teaching again!

What made you want to be a part of the sailing community?

I am from a family of sailors. My grandfather and mom used to sail 49ers competitively and I started sailing our laser at my cottage in the Gaspé when I was about 6. I spent years sailing dinghies, but when I was introduced to keelboats, Bob Marley, and not going home with bruised knees, I knew that cruising was for me. I do love a good run on a laser still though (congrats to Bruce too!!).

What is your favourite aspect of being an instructor/official?

I love passing along my love of sailing to others and helping them realize that they too can perform any maneuver out on the boat, regardless of their age or abilities. There are many ways to get a job done. I think that anyone can do anything when they are provided the right tools and support.

What is one of the most memorable moments that you have had as an instructor/official?

I think my most memorable moment was when I was teaching at the Royal Vancouver Yacht Club. I met a very special kid named Morgan, and he has made me want to be the best teacher I can be ever since. I actually looked up Morgan recently to see what he was up to, and to no surprise to me he became an Olympic ski racer.  

What would you say to someone who wants to start sailing, but isn’t sure they want to commit?

I would say find someone in your circle of friends who sails and ask them to take you out for an afternoon. You will quickly get a feel for what it is like to be on a boat and if you like it or not. Alternatively, get in touch with your local sailing school and ask for an intro sail! Sail Nelson offers free sails on Grandparents Day (to honour my grandparents) and there’s always the Intro to Keelboating 1-day course

Who inspired you be a better instructor/official?

I have been inspired by many other instructors over the years. Whether it is learning to teach something the way they taught it, or promising myself never to teach it the way they taught it!  I learn from everyone I encounter, and most of all I learn from my students and from their feedback. I never pretend to know everything and I leverage my sailing community for knowledge.

If you had one piece of advice to give to the sailing community, what would it be?

Be open and welcoming to those who want to join you. There is nothing wrong with being sea-sick, or showing up to the boat with jewelry on, or forgetting how to tie an eight knot… Remember that you were once in their shoes and had to learn how to sail too. You now have an opportunity to share your passion with others without judgement. Oh, and not everyone wants to become a racer!

Social Media Links:
Facebook  @sailnelsonbc
Twitter @sailnelsonbc
Instagram @sailnelsonbc

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