About Penny Caldwell

Knowledge. Confidence. Adventure.

For me, sailing has never been just about getting from one place to another. It’s about the adventure, the people you meet along the way, the challenges that make you think on your feet, and that wonderful feeling when you realize you’re capable of more than you thought.
After nearly three decades of teaching sailing, I’m still as passionate about helping people discover their confidence on the water as I was when I first started.

Whether you’re stepping aboard for the very first time, working toward becoming a confident skipper, or developing your skills as a sailing instructor, I’m here to help you learn, grow, and enjoy the journey.
And hopefully have a few good laughs along the way!

A Lifetime on the Water

My sailing story started when I was about a year old, tucked under my grandfather’s arm aboard our family Laser on the St. Lawrence River. Apparently, I enjoyed the experience enough to keep coming back!

My grandfather, Adrian, passed along his love of sailing, and it has been a huge part of my life ever since.

Over the years, I’ve sailed everything from little Optimists and Lasers to 50-foot cruising yachts. My adventures have taken me across Canada, through the Great Lakes and St. Lawrence River, along the beautiful coast of British Columbia, and across the Pacific Ocean from Hawaii to Victoria.

I’ve had some incredible experiences, met wonderful people, and learned a tremendous amount along the way. And, like most sailors, I’ve collected a few good stories about things that didn’t quite go according to plan.

One thing I know for certain: no matter how many years you’ve spent on the water, sailing always has something new to teach you.

From Sail Nelson to What’s Next

In 2017, I launched Sail Nelson, bringing professional sailing instruction to the beautiful waters of Kootenay Lake.

Over nine seasons, I had the privilege of building and running a successful sailing school, introducing people to sailing, helping boat owners become more comfortable with their vessels, and watching students progress from nervous beginners to capable, independent skippers.

We offered everything from introductory sailing experiences and basic cruising courses to advanced training, navigation, marine radio, and instructor development.

But what I enjoyed most wasn’t handing someone a certificate. It was watching that moment when everything clicked. When a student who was hesitant to take the helm suddenly realized, “Hey, I can actually do this!”

Those moments are what make teaching so rewarding.

Now, after nine wonderful seasons, I’m closing the Sail Nelson chapter and setting a new course.

My focus is shifting toward instructor development, marine consulting, professional sailing opportunities, and continuing my own sailing education and adventures.

And, of course, sharing everything I learn along the way.

Teaching the Teachers

I’m a Sail Canada Advanced Cruising Instructor and Senior Instructor Evaluator, with nearly three decades of experience teaching sailors and developing instructors.

Throughout my career, I’ve taught through sailing schools and yacht clubs across Canada, including Royal Vancouver Yacht Club, Humber College Sailing Centre, Pointe Claire Yacht Club, Royal St. Lawrence Yacht Club, and Advantage Boating.

These days, I’m particularly interested in supporting the next generation of sailing instructors.

Being a good sailor and being a good instructor are two very different skills. Knowing how to sail is one thing; knowing how to explain it, demonstrate it, and help someone else develop confidence is another.

I believe great instruction should be practical, supportive, engaging, and fun. Students should feel comfortable asking questions, making mistakes, and learning through experience.

My goal is to help instructors develop those skills so they can create the same positive learning experiences for their own students.

Your Pocket Sailing Instructor

One of my favourite projects is my podcast, Your Pocket Sailing Instructor.

I started the podcast to make quality sailing education more accessible, particularly for people who might not have easy access to courses, instructors, or regular time on the water.

Think of it as having a sailing instructor in your pocket, ready whenever you have a question or want to learn something new.

We talk about everything from boat handling, seamanship, safety, and maintenance to chartering, cruising, and the challenges of becoming a confident skipper.

There are also plenty of stories from my own adventures, lessons learned the hard way, and the occasional reminder that even experienced sailors make mistakes!

With more than 100 episodes and listeners in over 40 countries, the podcast has grown into a wonderful community of sailors who share a passion for learning and adventure.

A Free Knowledge Centre for Sailors

One of the reasons I created penny-caldwell.ca was to give the educational content from Sail Nelson a new home.

Over the years, I’ve accumulated a pretty extensive collection of articles, teaching resources, podcast episodes, checklists, and sailing tips. Rather than letting all that information disappear when I close the sailing school, I want to make it available to everyone.

This website is becoming a free sailing knowledge centre, with practical resources to help you build your skills and plan your next adventure.

You’ll find articles on seamanship, boat maintenance, safety, chartering, and cruising, along with downloadable guides, sailing itineraries, and podcast resources.

Whether you’re preparing for your first charter, brushing up on your navigation skills, or dreaming about your next destination, I hope you’ll find something useful here.

No complicated jargon or unnecessary fluff. Just practical sailing knowledge that you can put to work on the water.

Still Learning. Still Exploring.

Although I’ve spent much of my life teaching others, I’m very much a student myself.

I’m continuing to develop my offshore sailing experience, working toward my RYA Yachtmaster qualifications, and looking for opportunities to get involved in more offshore passages, racing, professional skippering, and boat deliveries.

There are also a few destinations on my sailing wish list. Greece, Spain, Italy, Norway, French Polynesia, New Zealand, the Caribbean… the list seems to get longer rather than shorter!

For me, that’s part of the magic of sailing. There is always another destination to explore, another skill to develop, and another adventure waiting just beyond the horizon.