Welcome
Sail Smarter. Go Further. Adventure More.
Practical sailing advice, real-world experience, and a little inspiration for your next adventure. Explore free sailing resources, listen to Your Pocket Sailing Instructor podcast, and build the confidence to take the helm.
More Confidence. More Adventure.
Sailing is a lifelong adventure, and there’s always something new to learn! Whether you’re just getting started, building your confidence as a skipper, or planning your next big sailing adventure, you’re in the right place. Explore practical tips, free sailing resources, real-world advice, and stories from the water—all designed to help you become a better sailor and have more fun along the way.
Helping sailors build confidence, develop skills, and discover just how far they can go.
Hi, I’m Coach Penny! With nearly 30 years of sailing instruction experience, I’m passionate about making sailing more accessible, less intimidating, and a whole lot more fun. As a Sail Canada Senior Instructor Evaluator, sailing school owner for nine seasons, and host of Your Pocket Sailing Instructor podcast, I love sharing practical knowledge, lessons learned, and a few stories along the way.
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Helping You Make the Most of Life on the Water
Whether you’re new to sailing or have thousands of nautical miles under your keel, there’s always something new to discover. My goal is to share what I’ve learned through years of teaching, sailing, and exploring—giving you practical tools, fresh inspiration, and the confidence to take your sailing adventures wherever you dream of going.
Build Your Sailing Confidence
From mastering the basics to making those big skipper decisions, I’ll share practical advice and real-world lessons to help you become a more confident, capable, and independent sailor.
Get Inspired to Explore
Discover incredible sailing destinations, chartering tips, cruising itineraries, and stories from adventures near and far. Whether you’re dreaming of your first overnight trip or a Mediterranean charter, I’ll help you turn those ideas into plans.
Learn Something New
Explore free sailing guides, helpful tips, maintenance advice, and lessons learned from nearly 30 years of teaching. No unnecessary jargon or complicated explanations—just useful information you can actually put to work.
Come Along for the Journey
Join me on Your Pocket Sailing Instructor podcast for conversations, sailing tips, personal experiences, and the occasional mishap! We’ll celebrate the successes, learn from the mistakes, and have a few laughs along the way.
The Adventure Never Stops. Neither Does the Learning.
One of the things I love most about sailing is that no matter how many miles you’ve travelled or how many years you’ve spent on the water, there’s always something new to learn. Every adventure brings new challenges, new experiences, and usually a few good stories!
Most Recent Articles & Podcast Episodes
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Your First Trip as Skipper: How to Get It Right
“Remember, every experienced skipper was once a beginner. The important thing is to get out there, keep learning, and enjoy the adventure!“ ~ Sailing According to Coach Penny There’s a moment in every sailor’s journey when you realize that you’re ready to take charge. No instructor beside you, no experienced skipper making the decisions. Just…
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Beating the Winter Blues – how I stay engaged in my sailing over the winter!
“Just because the boat isn’t moving doesn’t mean your sailing adventures have to stop!” ~ Sailing According to Coach Penny Alright, winter sucks for us northern sailors! True, I am lucky that my boat is in the water, but it’s cold! I haven’t sailed in months and I’m going through withdrawal (the winter blues)! So,…
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Don’t be a jerk! Boating Etiquette
“Good boating manners don’t cost a thing, but bad ones can ruin everyone’s day on the water!” ~ Sailing According to Coach Penny This week I am talking all about being a good boating neighbour! How to be a safe, and non-jerky, boater! There are a few unwritten rules to keep in mind about boating…
Your Next Adventure Starts Here
There’s a whole world out there waiting to be explored, and some of the best places are reached by sailboat! From hidden anchorages and charming coastal villages to unforgettable charter destinations, discover sailing inspiration, practical travel tips, and itineraries to help you plan your next adventure. Because sometimes the hardest part is deciding where to go next!
“Penny’s podcast is just what I was looking for! The right mix of information, education and common sense.”
“After my husband passed I was nervous to take out our boat. Penny’s episodes are giving me the confidence I need to keep learning and growing as a sailor.”
“It’s great to listen to a podcast that is not all about offshore sailing or the “look at me” skipper. The episodes are concise and to the point!”
Ways You Can Support Me
Love the free sailing content? Here are a few simple ways you can help keep the adventures, stories and sailing knowledge coming!
Listen to the Podcast
Tune in to Your Pocket Sailing Instructor! Whether you’re learning the ropes or have thousands of nautical miles under your belt, there’s something for everyone. Every listen, follow and review helps more sailors discover the podcast. And best of all, it’s completely free!
Support me on Patreon
Want to help keep the free sailing resources coming? Consider becoming a Patreon supporter! Your contribution helps cover the costs of creating podcasts, guides and other sailing content. Every little bit helps me continue sharing what I love with this amazing sailing community!
Follow me on Instagram
Come along for the ride! Follow me on Instagram for sailing adventures, behind-the-scenes moments, helpful tips and the occasional mishap (because let’s face it, sailing doesn’t always go according to plan!). Say hello, share your own adventures and let’s stay connected!
Share with a Fellow Sailor
Know someone who’s dreaming of learning to sail, planning their first charter or just loves being on the water? Send them my way! Sharing a podcast episode, article or free guide is one of the easiest ways to support what I’m doing. Good sailing knowledge is meant to be shared!
Join my Sailing Community
Sign up for my newsletter and stay in the loop! I’ll share new podcast episodes, sailing tips, free resources and news about upcoming adventures and flotillas. No unnecessary clutter in your inbox, just a little sailing inspiration now and then!
Send me Your Ideas & Questions
Some of my favourite teaching moments start with a great question! Have a sailing topic you’d love me to cover, a question that’s been puzzling you or a story to share? I’d love to hear it. Your ideas help shape future podcast episodes and resources for sailors everywhere.