Your Pocket Sailing Instructor

Your Pocket Sailing Instructor

By Penny Caldwell

Hey sailor! My name is Penny and I have been a sailing coach with Sail Canada for over 25 years! I have helped thousands of sailors find their passion and love of all things sailing. I'm here to help you live your best sailing life. I provide gear reviews, sailing tips, habits to perfect and much more! So, sit back and enjoy some informative, entertaining, unique sailing content! See you on the water ;-) Don't miss an episode! https://wavve.link/_QdonK50x/episodes
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05/19/26

Episode 4 Docking Without the Drama (Even in Tight Marinas) NEW SERIES: From Passenger to Confident Skipper!

Episode 4 of my new series From Passenger to Confident Skipper is all about docking! What equipment you need, how to practice and prepare for all scenarios, what to do with your crew, and more. Learn some expert tips on how to master docking your boa… Read more

05/11/26

Episode 3 The key decisions every skipper must get right NEW SERIES: From Passenger to Confident Skipper!

One of the biggest shifts in sailing happens when you move from simply operating the boat to making the decisions that keep everyone safe and confident on the water. In this episode of Your Pocket Sailing Instructor, I break down the five key decisio… Read more

04/27/26

Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper!

In Episode 2 of our series From Passenger to Confident Skipper, we dig into a frustrating but incredibly common feeling: you’ve spent time on the water, maybe even taken courses, yet that sense of true confidence still hasn’t clicked. Why? This episo… Read more

04/20/26

Episode 1 You've taken a course... now what? NEW SERIES: From Passenger to Confident Skipper!

I am staring an 8-episode series called "From Passenger to Confident Skipper". Each episode will focus on a different aspect of your voyage to becoming the most competent skipper you can be! This episode guides new sailors through the essential ste… Read more

04/06/26

#86 SailTies: Turning Every Voyage Into a Story

I am SO excited to introduce you all to Sailties! This is an awesome app for sailors where we can log our trips, exchange information, create a sailor resume, look for adventures to join, and so much more! Today I'm interviewing the co-founders Ch… Read more

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