Your Pocket Sailing Instructor Podcast

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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20 episodes
Updated June 8

Episodes20

Newest first

June 8 · 38 min
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
May 19 · 25 min
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 essentials Maneuvering your boat in tight spaces Planning and communication for docking success Chapters 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
May 11 · 22 min
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
April 27 · 24 min
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 confidence Practicing skills in controlled environments Handling crew overboard and emergency situations 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
April 20 · 24 min
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 practice Creating controlled environments for skill development Importance of repetition and routine in sailing Exposing yourself to different boats and conditions Building 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
April 6 · 33 min
#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 Website SailTies App on App Store SailTies on Google Play Chapters 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
March 9 · 26 min
#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 Takeaways Graham 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. Chapters 00:00 Introduction to Sailing and Boat Ownership 05:55 Renovations and Upgrades on Ringo 11:57 Future Boat Shopping Considerations 19:45 Sailing Experiences and Boat Performance 26:55 Researching and Selecting a New Boat 34:06 Lessons Learned from Boat Ownership 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
February 16 · 31 min
#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. Takeaways Consider 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. Chapters 00:00 Introduction to Buying a Boat 02:57 Understanding Your Boating Environment 05:47 Choosing the Right Boat Size and Type 08:58 Insurance and Budget Considerations 12:01 Evaluating Boat Condition and Maintenance 14:51 Test Driving Your Potential Boat 28:55 Recap and Final Thoughts 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
February 1 · 19 min
#83 Mastering Winches: A Sailor's Guide!
In this episode of Your Pocket Sailing Instructor, Penny discusses the essential sailing equipment known as winches. She provides a historical overview of winches, explaining their evolution and significance in sailing. The conversation covers different types of winches, including self-tailing and non-self-tailing options, and offers insights on how to choose the right winch for your boat. Penny shares her personal experiences and tips for operating winches effectively, making this episode a valuable resource for both novice and experienced sailors. takeaways Winches are crucial for controlling sails on a boat. The evolution of winches has significantly improved sailing efficiency. Self-tailing winches allow for easier sail management. Understanding winch types is essential for boat maintenance. Choosing the right winch size is important for performance. Historical context enriches our understanding of sailing equipment. Electric winches provide convenience on larger boats. Durability and material quality are key factors in winch selection. Proper operation of winches enhances sailing safety. Upgrading winches can improve overall sailing experience. 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
January 19 · 21 min
#82 Equipment Upgrades! NOW is the time!!
In this episode of 'Your Pocket Sailing Instructor,' Coach Penny Caldwell dives into the exciting world of boat show season, emphasizing the importance of taking advantage of sales and upgrades for your boat. She discusses the typical timing of boat shows in North America, which generally occur from January to March, and highlights the various items that can be upgraded or purchased at discounted prices during this period. Penny shares her personal experiences and recommendations for big-ticket items such as self-tailing winches, electronics, inflatable PFDs, and solar setups, all of which can significantly enhance the sailing experience. Penny also touches on frequently replaced items like first aid supplies, running rigging, and spare parts, encouraging listeners to check their inventory and replace any outdated or worn-out gear. She concludes with a discussion on comfort items that can make sailing more enjoyable, such as sailing gloves and innovative products like toques with built-in headlamps. Overall, this episode serves as a comprehensive guide for sailors looking to upgrade their equipment and make the most of the boat show season. Chapters 00:00 Introduction to Boat Show Season 02:37 Big Ticket Items to Consider 06:17 Electronics and Safety Gear Upgrades 09:30 Dinghies and Solar Power Solutions 11:48 Foul Weather Gear Essentials 14:08 Frequently Replaced Items 18:46 Comfort Items for a Better Sailing Experience 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
January 5 · 21 min
#81 Am I ready for the Intermediate Bareboat Sailing course?
Summary In this episode of Your Pocket Sailing Instructor, Penny Caldwell discusses the Intermediate Cruising Course, also known as ASA 104. She outlines the prerequisites for the course, including prior sailing experience and necessary certifications. The course focuses on real-life navigation skills, managing a crew, and enhancing sailing abilities beyond the basics. Penny emphasizes the importance of preparation and understanding crew dynamics to ensure a successful sailing experience. She also encourages listeners to immerse themselves in sailing culture to gain additional knowledge and skills. Takeaways The Intermediate Cruising Course prepares you for chartering. Prerequisites include basic sailing and navigation courses. Real-life navigation experience is crucial for success. Understanding crew dynamics is essential for a smooth trip. You should have prior sailing experience before taking the course. The course focuses on practical skills and real-time decision making. Effective provisioning and meal planning are part of the course. Communication of expectations with the crew is vital. Immersing yourself in sailing culture enhances learning. The course is designed for those ready to take on more responsibility. 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
Dec 29, 2025 · 33 min
#80: Three Generations, One Boat: A Sailing Story
This past summer I was lucky enough to take my grandparents, mom and daughter on a sailing trip! It was VERY special to be able to share this experience with 4 generations on the boat... In this episode I talk about my preparation, things to think about, where we went, why we went there and some highlights of the trip along the way. Filled my bucket!! 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
Dec 23, 2025 · 17 min
#79 Last Minute Christmas Gift Ideas!
Are you behind on your gifts this year? Not quite sure what to get your sailor? I've got you covered with a list of small to big gift ideas! 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
Nov 27, 2025 · 26 min
#78 Croatia 2025 Trip & Highlights!
Summary In this episode, Coach Penny shares her recent sailing adventure in Croatia, reflecting on her experiences from a previous trip and the differences in crew dynamics, boat choice, and anchoring strategies. She discusses the benefits of sailing on a catamaran, the importance of provisioning, and the beautiful anchorages she discovered. Penny also touches on the changing weather conditions and her future sailing plans, emphasizing the joy of relaxation and camaraderie during the trip. Takeaways Penny returned to Croatia for a more relaxed sailing experience. She chose a Lagoon 42 catamaran for more space and comfort. Provisioning boxes made meal planning easier and more efficient. Having experienced sailors on board allowed for a more enjoyable trip. The catamaran handled well in strong winds, reaching impressive speeds. Penny preferred anchoring in quieter locations away from crowds. Weather changes impacted the trip, signaling the end of the sailing season. The trip was a refreshing break from her usual coaching responsibilities. Penny plans to explore other sailing destinations in the future. She looks forward to sharing more adventures from her summer travels. 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
Jan 27, 2025 · 15 min
BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound
Bonus episode created with Google Notebook LM.
Jan 27, 2025 · 29 min
#77 Creating an Itinerary! The basic steps...
Have an exciting trip in mind? This week I'm talking about creating an itinerary plan. How do I do it? What are the steps? Where should you spend the money and where can you save?
Jan 1, 2025 · 16 min
#76 Desolation Sound Mayday! :-(
This week I'm talking about a Mayday call we overheard while in Desolation Sound this past summer... Happy New Year and here's to 2025! 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
Dec 23, 2024 · 20 min
#75 Last Minute Gift Ideas for your Sailor!
I am WAY behind on my shopping this year, so thought I'd help put together some last minute ideas for you as well! Happy Holidays and looking forward to seeing you in 2025! Audio does not seem to be great this time around again. Still sorting out this new recording software they are making me use... sorry! 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
Nov 11, 2024 · 15 min
#74 My Experience with AI ... yikes!
This week my friend Bob sent me a new tool called Google NotebookLM. I plopped my sailnelson.com website address into their system and within 5 minutes they sent out a 15 min podcast episode! It even has 2 presenters, loads of information from the website... I was a bit shocked. Have a listen and let me know what you think!
Nov 4, 2024 · 27 min
#73: Winterizing... we've come full circle LOL!
I'm back! FINALLY! Excited to be bringing a new episode to you! From a new house, new studio, and a new podcasting software! Yikes. This week I'm digging into Winterizing as we have two boats to winterize this year: one in the water, and one on the hard! I talk a bit about the differences. Here you go!

Your Pocket Sailing Instructor Podcast

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

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

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

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

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

#86 SailTies: Turning Every Voyage Into a Story

#85 From Impulse to Informed: Graham's Boat Buying Journey

#84 Essential Tips for First-Time Boat Buyers!

#83 Mastering Winches: A Sailor's Guide!

#82 Equipment Upgrades! NOW is the time!!

#81 Am I ready for the Intermediate Bareboat Sailing course?

#80: Three Generations, One Boat: A Sailing Story

#79 Last Minute Christmas Gift Ideas!

#78 Croatia 2025 Trip & Highlights!

BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound

#77 Creating an Itinerary! The basic steps...

#76 Desolation Sound Mayday! :-(

#75 Last Minute Gift Ideas for your Sailor!

#74 My Experience with AI ... yikes!

#73: Winterizing... we've come full circle LOL!