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Your Pocket Sailing Instructor Podcast

Your Pocket Sailing Instructor Podcast

Penny Caldwell 103 Episodes Jun 8, 2026

Host Penny Caldwell, a sailing coach with over 25 years of experience and a Sail Canada certification, shares her expertise on the podcast. Each episode offers practical sailing tips, gear reviews, and advice on building good habits on the water. The show aims to help sailors of all levels improve their skills and deepen their love for sailing.

Episodes

Episode 5 Anchoring: Stop dragging for good NEW SERIES: From Passenger to Confident Skipper!
Episode 5 Anchoring: Stop dragging for good NEW SERIES: From Passenger to Confident Skipper! Jun 8, 2026 00:38:20 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. Chapters00:00 Understanding Different Types of Anchors14:12 Choosing the Right Anchor for Your Needs16:58 Ideal Anchoring Conditions and Bottom Types17:30 Understanding Anchoring Basics27:36 Advanced Anchoring Techniques32:11 Steps to Successfully A
Episode 4 Docking Without the Drama (Even in Tight Marinas) NEW SERIES: From Passenger to Confident Skipper!
Episode 4 Docking Without the Drama (Even in Tight Marinas) NEW SERIES: From Passenger to Confident Skipper! May 19, 2026 00:25:21 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 TopicsDocking equipment essentialsManeuvering your boat in tight spacesPlanning and communication for docking successChapters0
Episode 3 The key decisions every skipper must get right NEW SERIES: From Passenger to Confident Skipper!
Episode 3 The key decisions every skipper must get right NEW SERIES: From Passenger to Confident Skipper! May 11, 2026 00:22:47 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
Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper!
Episode 2 Why you still don’t feel confident sailing NEW SERIES: From Passenger to Confident Skipper! Apr 27, 2026 00:24:43 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 explo
Episode 1 You've taken a course... now what? NEW SERIES: From Passenger to Confident Skipper!
Episode 1 You've taken a course... now what? NEW SERIES: From Passenger to Confident Skipper! Apr 20, 2026 00:24:54 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 an
#86 SailTies: Turning Every Voyage Into a Story
#86 SailTies: Turning Every Voyage Into a Story Apr 6, 2026 00:33:01 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 r
#85 From Impulse to Informed: Graham's Boat Buying Journey
#85 From Impulse to Informed: Graham's Boat Buying Journey Mar 9, 2026 00:26:46 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
#84 Essential Tips for First-Time Boat Buyers!
#84 Essential Tips for First-Time Boat Buyers! Feb 16, 2026 00:31:43 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
#83 Mastering Winches: A Sailor's Guide!
#83 Mastering Winches: A Sailor's Guide! Feb 1, 2026 00:19:44 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 s
#82 Equipment Upgrades! NOW is the time!!
#82 Equipment Upgrades! NOW is the time!! Jan 19, 2026 00:21:03 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 dis
#81 Am I ready for the Intermediate Bareboat Sailing course?
#81 Am I ready for the Intermediate Bareboat Sailing course? Jan 5, 2026 00:21:45 SummaryIn 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 importan
#80: Three Generations, One Boat: A Sailing Story
#80: Three Generations, One Boat: A Sailing Story Dec 29, 2025 00:33:18 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

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