Your Pocket Sailing Instructor Podcast

Penny Caldwell
  • 4.9 (37)
  • 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. 1D AGO

    #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

    32 min

  2. FEB 1

    #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

    20 min

  3. JAN 19

    #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

    21 min

  4. JAN 5

    #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

    22 min

  5. 12/29/2025

    #80 Multi-generational Sailing Trip!

    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

    33 min

  6. 12/23/2025

    #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

    17 min

  7. 11/27/2025

    #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

    27 min

  8. 01/27/2025 · BONUS

    BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound

    Bonus episode created with Google Notebook LM.

    16 min
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4.9
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37 Ratings

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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