Your Pocket Sailing Instructor Podcast
Your Pocket Sailing Instructor Podcast

Your Pocket Sailing Instructor Podcast

Penny Caldwell

Overview
Episodes

Details

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

Recent Episodes

Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper!
APR 27, 2026
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 episode breaks down the hidden gaps between knowledge and real-world decision-making, and why simply “getting more experience” isn’t always enough.We explore the subtle factors that hold sailors back—like over-reliance on others, lack of deliberate practice, and not fully understanding the “why” behind key skills. You’ll hear relatable scenarios that many developing sailors face, from second-guessing decisions at the helm to feeling uneasy in changing conditions. If you’ve ever wondered why confidence seems to come easily to others but not to you, this episode will help reframe that thinking.Most importantly, we talk about how to move forward. You’ll learn practical ways to take ownership on the boat, build trust in your decisions, and turn passive experience into active learning. Confidence isn’t something you wait for—it’s something you build, intentionally, one skill and one decision at a time. key topicsBuilding sailing confidencePracticing skills in controlled environmentsHandling crew overboard and emergency situationsHead over to sailnelson.com to download your free Episode 1 download!⁠ A cheat sheet of all the different things you can practice, and when, after your first course. Connect with Penny:- ⁠⁠⁠⁠Support Penny on Patreon! ⁠⁠⁠⁠- ⁠⁠⁠⁠Learn more about Penny's sailing school!⁠⁠⁠⁠- ⁠⁠⁠⁠Get in touch!⁠⁠⁠⁠- ⁠⁠⁠⁠Take a course! ⁠⁠⁠⁠- ⁠⁠⁠⁠Penny's sailor resume⁠⁠⁠⁠-⁠⁠⁠⁠ Instagram⁠
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24 MIN
#85 From Impulse to Informed: Graham's Boat Buying Journey
MAR 9, 2026
#85 From Impulse to Informed: Graham's Boat Buying Journey
In this conversation, Graham shares his journey into sailing and boat ownership, detailing his experiences with purchasing his first boat, Ringo, and the lessons learned along the way. He discusses the importance of research in selecting the right boat, the renovations and upgrades he undertook, and his future considerations for boat shopping. The conversation highlights the challenges and joys of sailing, as well as the practical aspects of boat maintenance and ownership.Keu TakeawaysGraham started sailing in 2017 and became an instructor.His first boat purchase was impulsive and not well-researched.Ringo, a CNC 25, was chosen for its sailing performance and comfort.Researching boat models and their issues is crucial before buying.Renovations on Ringo included addressing blisters and upgrading rigging.Graham learned a lot about boat maintenance through hands-on experience.Future boat shopping will focus on comfort and readiness for cruising.Non-negotiables for the next boat include a dry head and separate shower.Budget and intended use are key factors in the boat buying process.Sailing experiences have shaped Graham's wishlist for his next boat.Chapters00:00 Introduction to Sailing and Boat Ownership05:55 Renovations and Upgrades on Ringo11:57 Future Boat Shopping Considerations19:45 Sailing Experiences and Boat Performance26:55 Researching and Selecting a New Boat34:06 Lessons Learned from Boat OwnershipConnect with Penny!- ⁠⁠Support Penny on Patreon! ⁠⁠- ⁠⁠Learn more about Penny's sailing school!⁠⁠- ⁠⁠Get in touch!⁠⁠- ⁠⁠Take a course! ⁠⁠- ⁠⁠Penny's sailor resume⁠⁠-⁠⁠ Instagram⁠
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26 MIN
#84 Essential Tips for First-Time Boat Buyers!
FEB 16, 2026
#84 Essential Tips for First-Time Boat Buyers!
In this episode of Your Pocket Sailing Instructor, Coach Penny discusses essential considerations for buying a boat. She emphasizes the importance of understanding your boating environment, choosing the right size and type of boat, and the significance of insurance and budget. Penny also covers how to evaluate a boat's condition and the importance of test driving before making a purchase. The episode concludes with a recap of key points and encouragement to enjoy the sailing journey.TakeawaysConsider where you will be boating and the type of boating you will do.The size of the boat should match your sailing needs.Marinas may have long wait lists for boat slips.Insurance requirements can vary significantly by marina.Evaluate the condition of the boat before purchasing.Test drive the boat to understand its handling.Look for any major issues during the boat survey.Collect insurance quotes early in the buying process.Consider the amenities available at your marina.Enjoy the process of finding the right boat.Chapters00:00 Introduction to Buying a Boat02:57 Understanding Your Boating Environment05:47 Choosing the Right Boat Size and Type08:58 Insurance and Budget Considerations12:01 Evaluating Boat Condition and Maintenance14:51 Test Driving Your Potential Boat28:55 Recap and Final ThoughtsConnect with Penny!- ⁠Support Penny on Patreon! ⁠- ⁠Learn more about Penny's sailing school!⁠- ⁠Get in touch!⁠- ⁠Take a course! ⁠- ⁠Penny's sailor resume⁠-⁠ Instagram⁠
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31 MIN