Podcast
Your Pocket Sailing Instructor Podcast
Sailing knowledge you can take anywhere.
Practical Sailing Knowledge, Wherever Your Adventure Takes You
Welcome to Your Pocket Sailing Instructor — the sailing podcast designed to help you become a more knowledgeable, capable and confident sailor!
Drawing on more than 30 years of sailing and teaching experience, I share practical advice, real-world stories and lessons learned on everything from boat handling and seamanship to maintenance, safety, chartering and cruising. Whether you’ve just started sailing or you’re preparing to take command of your own boat, there’s always something new to learn.
With 200,000+ plays and downloads, 100+ episodes and listeners in more than 40 countries, Your Pocket Sailing Instructor is helping sailors around the world build their skills and confidence on the water.
Ready to keep learning? Grab your headphones and let’s go sailing.
Apparently, I’m not just talking to myself!
With more than 200,000 plays and downloads, 100+ episodes and listeners in more than 40 countries, Your Pocket Sailing Instructor has found its way onto boats, docks, commutes and probably a few boat-project workbenches around the world.
200K+
downloads
40+
countries

Your Pocket Sailing Instructor is heard around the world, helping sailors everywhere build their knowledge, confidence and skills on the water.
Recent Episodes
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When Things Go Sideways: Staying Calm Under Pressure
“When things start going wrong on the water, your greatest asset isn’t speed—it’s your ability to slow the situation down.” ~ Sailing According to Coach Penny Every sailor eventually has one of those moments. The docking approach isn’t working. The wind suddenly picks up. The engine won’t start when you need it. A crew member…
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Seasickness!!
“Seasickness can ruin a day—but planning ahead can make a huge difference.“ ~ Sailing According to Coach Penny If you know you are prone to seasickness, make your prevention plan before departure. Once you are already sick, every solution becomes harder to manage. What You’ll Learn Seasickness is incredibly common, and it does not care…
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Which Sailing Course Do I Take?
“Choose a course based on what you want to be able to do after it – not simply the next certificate in the sequence. Your sailing goal should drive your training plan.” ~ Sailing According to Coach Penny So you have decided you want to learn to sail—fantastic. The next question is usually, ‘Which course…
Want to Dig a Little Deeper?
Some sailing topics deserve more than one episode! I’ve grouped together episodes that build on one another, giving us a chance to explore a subject in more detail. Whether you’re working toward taking command, trying to figure out what kind of sailor you want to be, or simply want to understand your sails a little better, these series are a great place to start.
From Passenger to Confident Skipper
Ready to take the helm?
You’ve taken some courses and spent time aboard — but being the person ultimately responsible for the boat still feels like a pretty big leap. This series is designed to help bridge the gap between knowing how to sail and having the confidence to take command.
We’ll tackle practical skills such as docking and anchoring, but we’ll also explore something just as important: how a good skipper thinks, plans and makes decisions.
EXPLORE THE SERIES →
What Kind of Sailor Do You Want to Be?
Where do you want sailing to take you?
There’s no single right way to be a sailor. Maybe you’re happiest day sailing close to home. Perhaps racing appeals to your competitive side. Or maybe you’re dreaming about living aboard or eventually heading offshore.
In this four-part series, I explore day sailing, racing, liveaboard sailing and offshore sailing to help you think about your goals — and what skills and experience you’ll need to get there.
EXPLORE THE SERIES →
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