Your Pocket Sailing Instructor Podcast

Penny Caldwell
  • 5.0 (41)
  • How To
  • Updated Weekly

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

  1. 2d ago

    Episode 7 The Skipper Mindset Shift NEW SERIES: From Passenger to Confident Skipper!

    There comes a point in almost every sailor's journey when you realize something interesting: you probably already know more than you think you do! You can steer the boat. You understand the sails. You can dock, anchor, navigate and keep watch. You've learned how to communicate with your crew, make decisions and deal with things when they don't go according to plan. But there's still one big step left. Saying, "I'm the skipper." And surprisingly, that can be one of the hardest steps of all.

  2. Sep 29

    Episode 6 When Things Go Sideways: Staying Calm Under Pressure NEW SERIES: From Passenger to Confident Skipper!

    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 becomes sick. Something breaks. Or perhaps several small things start happening at exactly the same time. It's easy to think that becoming a confident skipper means reaching a point where these situations don't happen anymore. They do. Boats break, weather changes, people make mistakes, and occasionally our carefully constructed plans go completely sideways. The difference isn't that experienced skippers avoid problems. It's that they learn how to manage them. In Episode 6 of my From Passenger to Confident Skipper series, we're talking about one of the most important skipper skills of all: staying calm when things don't go according to plan. What You'll Learn In this episode, we'll explore: What panic actually looks like aboard a boat—and how quickly it can escalate a manageable situation Why creating time and space is often your first priority How to recognize when it's time to abandon a plan and reset How to identify the most important problem when several things are happening at once Why clear communication becomes even more important under pressure How preparation and practice make calm decision-making easier Why experienced skippers aren't afraid to say, "This isn't working. Let's try again." How to turn stressful experiences into valuable skipper experience

  3. Jun 8

    Episode 5 Anchoring: Stop dragging for good NEW SERIES: From Passenger to Confident Skipper!

    This episode we talk about anchoring! What, how, when, where... all the ins and outs of making sure the boat stays put, so you can have a great sleep. Chapters 00:00 Understanding Different Types of Anchors 14:12 Choosing the Right Anchor for Your Needs 16:58 Ideal Anchoring Conditions and Bottom Types 17:30 Understanding Anchoring Basics 27:36 Advanced Anchoring Techniques 32:11 Steps to Successfully Anchor Your Boat ⁠Head 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

  4. May 19

    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 boat with confidence.  Key Topics Docking equipment essentialsManeuvering your boat in tight spacesPlanning and communication for docking successChapters 00:00 Introduction to Docking Challenges 03:34 Essential Equipment for Docking 06:46 Maneuvering Techniques for Docking 09:30 Common Mistakes and Crew Communication 14:44 Setting Up for Successful Docking 22:16 Conclusion and Next Steps Head 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

  5. May 11

    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 decisions every skipper needs to get right—from weather calls and route planning to docking strategies and knowing when it’s time to turn back. These are the moments that define good seamanship far more than perfect boat handling ever will.I also share real-world examples of how small decisions can quickly become big problems when they’re delayed or ignored. Whether it’s pushing on in changing weather, approaching a marina without a clear plan, or underestimating crew fatigue, the pressure to “just keep going” can lead skippers into situations they didn’t intend to be in. Learning to make calm, early decisions is one of the most valuable skills a sailor can develop. If you’re working toward becoming a more confident skipper, this episode will help you think differently about leadership, preparation, and responsibility on the water. It’s not about being perfect—it’s about building the judgment and awareness that allow you to make smart calls before situations escalate. key topics Skippers are defined by the decisions they make.The decision to go sailing can be challenging.Understanding timing and routes is crucial for safety.Docking requires careful planning and preparation.Knowing when to turn back is essential for safety.Anchoring safely is vital for overnight trips.Good skippers make decisions early based on observations.Practice decision-making skills at home.Safety of the crew should always be the priority.Every sailing outing is an opportunity to learn. 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

  6. Apr 27

    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 topics Building 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

  7. Apr 20

    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 steps after completing a sailing course, emphasizing practical experience, skill repetition, and creating a safe learning environment to build confidence and competence on the water. Key Topics I will Discuss: Post-course sailing practiceCreating controlled environments for skill developmentImportance of repetition and routine in sailingExposing yourself to different boats and conditionsBuilding confidence and decision-making skills Head 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

  8. Apr 6

    #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 Chris and Tom. They will outline all of the incredible benefits that this app includes. I am very excited about how this app is going to modernize my own record keeping and will help me avoid having so many logbooks! I also love the engagement that it creates between sailors and it is SO much better than trolling Facebook and other forums trying to find competent people to sail with. Thank you so much Chris and Tom for creating this awesome product! Download SailTies now!SailTies Official WebsiteSailTies App on App StoreSailTies on Google PlayChapters 00:00 Introduction to SailTies and Founders' Background 03:38 Prototyping and Feedback Process 06:00 User Experience and App Features 08:52 Future Developments and Enhancements 11:29 Safety Features and Community Engagement 14:17 Bridging the Experience Gap in Sailing 16:49 Reception and Growth of SailTies 19:17 Community Impact and User Feedback 23:58 Team Dynamics and Marketing Challenges 25:34 Partnerships and User Engagement 28:33 Finding the Right Crew and Personality Fit

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About

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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