Penny Caldwell

Your Pocket Sailing Instructor Podcast

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

Author

Penny Caldwell

Category

Education

Podcast website

sailnelson.com

Latest episode

Jun 8, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

#27: How to be a prepared sailing crew 21.07.2022

This week I am talking all about how to be a prepared crew. You have been invited out on a boat. Maybe you are racing, day sailing, or spending the weekend. What should you bring? How should you prepare? Which items are essential? I'll help you sort through the ins and outs of heading out sailing with someone else to make sure you make a great first impression and are invited back! To get yourself...

#26: Sailing with your spouse... 07.07.2022

Sailing with your spouse can be a challenge and also a great adventure! This week I chat about why I think it is important for you both to take lessons and learn everything you can together. I also talk about what to do if your spouse is not into sailing... *gasp* More show notes coming soon! 

#25: Purchasing & owning a boat! Now what? 30.06.2022

What an exciting adventure you are embarking on! Boat ownership! I hope you have deep pockets ;-) lol. Kidding. Owning a boat can be a very satisfying and rewarding thing, especially if you enjoy putting in some elbow grease and getting to know your new vessel. But, before you jump in with both feet, what should you do? Support me on  Patreon ! Should you get a survey? This is a loaded questi...

#24: Boat Buying 101: Avoid Costly Mistakes 23.06.2022

So you are looking at boats! This week on   Your Pocket Sailing Instructor podcast I am going to share with you some key information and questions that you should ask yourself and consider when purchasing your first boat. Support me on  Patreon !What type of sailing do you want to do? So a big part of your boat shopping will revolve around the type of sailing you want to do. Are you looking to rac...

#23: Top 10 Sailing Knots 09.06.2022

This week on  Your Pocket Sailing Instructor podcast  we are digging into knots! This is a list of the top 10 knots I use when sailing. I think that they are valuable and you should learn them as well. Being able to tie quick, efficient and reliable knots is key for your sailing toolbox. Support me on  Patreon ! Top 10 Sailing Knots #1 Bowline Description: the bowline creates a non-...

#22: 5 Seamanship Skills Every Confident Sailor Must Know 02.06.2022

This week on Your Pocket Sailing Instructor podcast we are digging into your seamanship toolbox! What should you focus on? What is seamanship anyway? Below I will explain my top 5 seamanship skills that I think you should master to make sure your trip is an uneventful success! :-)Support me on Patreon! Top 5 Seamanship Skills to Master#1 HelmingThe art of helming is the art of controlling your boa...

#21: What to expect from your sailing coach 26.05.2022

So your sailing school has told you what to expect from your course , but what should you expect from your sailing coach? There are many different teaching styles and several different learning types. Depending on how you like to learn, your sailing coach might have to get creative. However, there are some key things that you should expect from them. Here are my thoughts... Support me on  Pat...

#20: How to prepare for your sailing course! 19.05.2022

Alright, so you listened to my last episode and you have signed up for a course! Congrats! Now what? Hopefully the sailing school that you signed up with will be providing you with some pre-course learning materials. But if that is not the case, this week I provide you with some ideas. For this episode I will assume you are signed up for a day sailing course. I'll do a different episode for liveab...

#19: Which Sailing Course Do I Take? 12.05.2022

So you have decided to take up sailing! Great! But where do you start?! There are a lot of options out there so this week I'm going to dive into figuring out which course is for you. Here are some of my insider opinions on what to think about when signing up for your sailing course. Support me on Patreon ! Sign Up for the Podcast Be sure to sign up for my Podcast on  iTunes  or  Spo...

#18: Seasickness!! 05.05.2022

This week I am diving into a much dreaded topic: seasickness! Arg. No one enjoys this one, but it must be discussed as it can GREATLY impact your boat! We will take a look at all facets of this lovely experience from definition, to prevention, to management! Support me on Patreon ! Sign Up for the Podcast Be sure to sign up for my Podcast on  iTunes  or  Spotify  or find it on...

#17: Sailing Goals - Offshore Sailing 28.04.2022

This episode is for those of you who are interested in offshore sailing. Unlike my other episodes in this Sailing Goals series, I am not going to focus so much on courses. Instead I'm going to focus on physical and mental preparation required for offshore sailing. In 2018 I participated in a boat delivery for the Vic-Maui International Yacht Race . What an adventure it was! Support me on  Pat...

#16: Sailing Goals - Liveaboard Sailing 21.04.2022

This week we are talking about my favourite kind of sailing! Bareboat cruising or living on the boat for a few days, weeks, months or years! I really enjoy the pace and lifestyle of being on a boat. Don't get me wrong, a garden and yard for the kids to play in is also great, but I do love spending extended days on a boat. This episode is geared to those sailors who are thinking about spending more...

#15 Sailing Goals - Racing 14.04.2022

This is episode #2 in a four-part series I am doing on sailing goals. These episodes are aimed at helping you to figure out which courses to take, habits to form, and areas to focus on depending on where you want to end up! This second episode is geared to the race sailor who wants to move into the world of racing. Whether you are looking for weekend races, or offshore races, I'll talk about how y...

#14: Sailing Goals - Day Sailing 07.04.2022

This is episode #1 in a four-part series I am doing on sailing goals. These episodes are aimed at helping you to figure out which courses to take, habits to form, and places to go with your sailing depending on where you want to end up! This first episode is geared to the new sailor who wants to become the most proficient and able day sailor there is. Explore your own backyard with knowledge and h...

#13: I Need New Sailing Boots! 24.03.2022

Alright, so my boots are not as bad as the photo above, but I have had my sailing boots way too long! I need new ones. They have no tread, and have never fit properly. I bought them on sale, and thought what the heck? So, this week I am going to take you along on a gear shopping trip. Support me on Patreon ! What do I need? First off I need to figure out what I need. I currently have Keen sandals...

#12: Crew Dynamics: Who do you recruit? 03.03.2022

This week I am bringing you a shorty episode about crew dynamics and how I go about selecting a crew for offshore, or longer distance sails. I will also be moving to by-weekly episodes while I get a few things sorted out for this upcoming season! Hope you enjoy and let me know how you go about selecting your crew or how you interview your skipper!  Penny

#11: Base Layers! How to layer up for the occasion... 17.02.2022

Following along on last week's episode about foul weather gear, this week I am diving into base layers! These layers complement your external gear. Their job is to help manage your body heat and keep sweating to a minimum. Nice and dry = warmth! Support me on  Patreon ! What are the typical types of base layer fabrics? Synthetic Fabrics One of the most common synthetic fabrics used for base l...

#10: Foul Weather Gear Selection: My Top Tips! 10.02.2022

Foul weather gear is a large investment in your sailing gear, however if you select the appropriate gear for the kind of sailing you are planning to do, it can be invaluable. Today I will bring you through my Foul Weather Gear Checklist. It is my fail safe shopping list to make sure you get the gear you need. FREEBIE ALERT! Download my FREE foul weather gear selection checklist to help you make su...

#9: Must-Read Sailing Books 03.02.2022

I am a real bookworm, and so this week I am going to share some of my favourite sailing books. These are novels and not related to coaching, educating or learning anything new. They are just for me and just for fun! The descriptions I have provided are from The Nautical Mind or Amazon.ca. Support me on Patreon! And so, here is a short list of the sailing books that have really stuck with me after...

#8: Overcoming a #boatfail! 27.01.2022

There's nothing more humbling than having things not go as planned! We have all been there. You prepare, you're ready to go, and then wham! Not what you intended to have happen! What the heck? It happens to us all, and there are several things you can do to get your confidence back after a #boatfail. Support me on  Patreon ! Common #boatfails Docking: hitting dock, hitting another boat, not e...

#7: Day Sailing Done Right: What You Need to Know 20.01.2022

This week I am giving you the foundation of a successful day trip plan. There are key pieces of information that you should include, and I’m going to provide you with my pro tips and tricks! Support me on   Patreon !Sections of Your Trip Plan Document Boat – key information and unique features Crew – who and emergency contact info Itinerary – destinations and locations (GPS coordinates) Emergency...

#6: 10 Ways to Meet Other Sailors 06.01.2022

This week I’m all about helping you meet other like-minded sailors! And they DO exist. I promise. So whether you’ve had a hard time getting into the “boys club” or you don’t know where to start to look for sailing friends, here are some of my suggestions! Support me on  Patreon ! Off-Season Training: Boating Skills Here is a list of things you can work on in the off-season that will increase...

#5: Maritime Mysteries & Mishaps: Old Presque Isle Lighthouse 30.12.2021

The Old Presque Isle Lighthouse has been out of service for over a century now. However, that does not stop one of it's recently deceased keepers from lighting it up from time to time to safely lead ships into harbour.  With no lens, and no electricity leading to the lamp room, it is unknown how the lighthouse glows time and time again. Ghost hunters, historians and locals are mystified by th...

#4: Stay Sharp All Winter: Off-Season Training for Sailors 23.12.2021

This episode will focus on helping you figure out how to improve your knowledge and skill in the off-season! So if you winterize your boat, or just take a break for a few months, here are some ideas on where you can focus your energy! Support me on Patreon !Off-Season Training: Boating Skills Here is a list of things you can work on in the off-season that will increase your seamanship skills: Knot...

#3: Safety Gear Every Sailor Needs (No Exceptions) 16.12.2021

This episode is all about the required safety gear. We start off talking about the various acts, rules and regulations that make up the framework for safe boating in Canada and then expand from there. Support me on Patreon ! The Acts & Regulations Here is the list of acts and regulations that I touched on include: Canada Shipping Act Small Vessel Regulations Collision Regulations Boating Restr...

Listen to the Your Pocket Sailing Instructor Podcast podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.