Your Pocket Sailing Instructor Podcast

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

Episodes

December 29, 2025 33 mins

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!!

Mark as Played

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!

Mark as Played
November 27, 2025 26 mins

Well I had an amazing trip to Croatia recently! Was so different from my last trip... will tell you all about it today! Enjoy! Glad to be back!!

Mark as Played

Bonus episode created with Google Notebook LM.

Mark as Played

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?

Mark as Played
January 1, 2025 16 mins

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!

Mark as Played
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!
Mark as Played
November 11, 2024 15 mins

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!

Mark as Played

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!

Mark as Played
June 3, 2024 28 mins

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!

Mark as Played

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.

Mark as Played

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!

Mark as Played
April 15, 2024 24 mins

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

Mark as Played
March 25, 2024 18 mins

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

Mark as Played

This week I have an interview with my friend and instructor Graham! Graham came to Croatia with me in 2022 and loved it so much that he returned in 2023. He's here to share some of his chartering tips and tricks! Enjoy!

Mark as Played
February 26, 2024 23 mins

Are you looking for something unique to gift the sailor in your life? I've pulled together a list of some unique experiences to think about!

1. Sunset Sailing Cruise: Gift a serene evening sailing experience, allowing the sailor to enjoy the beauty of a sunset over the water.
2. Private Sailing Lesson: Arrange for a personalized sailing lesson with a professional instructor to help improve skills and confidence on the wate...

Mark as Played
February 5, 2024 32 mins

This week I am providing you with a personalized playlist depending on where you are in your sailing journey. For those of you who are new to the podcast, welcome aboard and this will give you an idea on what to listen to! For those of you who have been around awhile, thank you, and this is a great playlist to review past episodes and important info. Enjoy!


Please consider supporting me on Patreon at https://www.patreon.com/y...

Mark as Played
January 29, 2024 19 mins

Well, I have a dirty secret to share this week... Ugh. Enjoy!


Don't forget to check out my Patreon page a patreon.com/yourpocketsailinginstructor ! Thanks for the ongoing support!

Mark as Played

This week I am discussing crew dynamics (again) and some conflict resolution ideas. Ideally you avoid these conflicts form the beginning, but we all know that doesn't always happen!


I hope you find some useful tips and please remember to like, share and subscribe to keep up to date on my episodes! Don't forget to check out PATREON as well https://www.patreon.com/yourpocketsailinginstructor


Penny

Mark as Played
January 15, 2024 26 mins

Are you looking to explore the world of solo sailing? I highly recommend it!! There are many benefits of solo sailing including: flexibility, adventure, problem-solving, personal satisfaction, etc.


There are also several areas where you should focus your efforts to make sure your sail goes off without a hitch: planning, skill acquisition (especially reefing and docking), safety equipment upgrades, etc.

Mark as Played

Popular Podcasts

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    The Bobby Bones Show

    Listen to 'The Bobby Bones Show' by downloading the daily full replay.

    Crime Junkie

    Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.

    The Clay Travis and Buck Sexton Show

    The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.