Your Pocket Sailing Instructor Podcast

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 Successf...

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 Chapt...

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 th...

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 exp...

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 a...

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...

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...

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...

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...

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...

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 importa...

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 Patre...

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

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 an...

Bonus episode created with Google Notebook LM.

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?

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

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...

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!

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!

This week I am digging into standing rigging checks thanks to a Patron! For those of you looking to offer some support, head on over to Your Pocket Sailing Instructor Podcast - Penny Caldwell | creating awesome podcast episodes, useful checklists, & free dow | Patreon to check it out!

This week I'm giving you some Spring maintenance/check ideas and chatting about a shake down sail to get yourself set up for success! Spring Maintenance Checklist available for free download at sailnelson.com/podcast! Episode #51.

This week I am answering a question that I get asked A LOT! How to get more experience in between courses. Not an easy task sometimes! Thanks for the question Ell, and please let me know what kind of sailing groups you guys have found to be useful! Enjoy!

Finishing up our tender discussions and talking a bit more about how I am selecting my tender.

This week I'm diving into a Spindrift project and researching new tenders. My last one met an unfortunate, and unexpected, end. Enjoy!