DiscoverYour Pocket Sailing Instructor Podcast
Your Pocket Sailing Instructor Podcast

Your Pocket Sailing Instructor Podcast

Author: Penny Caldwell

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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!
85 Episodes
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! 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!
#70 Tender 2.0

#70 Tender 2.0


Finishing up our tender discussions and talking a bit more about how I am selecting my tender.
#69 New Tender Time!

#69 New Tender Time!


This week I'm diving into a Spindrift project and researching new tenders. My last one met an unfortunate, and unexpected, end. Enjoy!
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!
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 water.3. Weekend Sailing Getaway: Provide a weekend getaway aboard a chartered sailboat, offering the sailor a chance to explore new waters and destinations.4. Racing Regatta Participation: Enroll the sailor in a local sailing regatta or race, providing an exhilarating and competitive experience on the water.5. Sailing Expedition Adventure: Gift an adventurous sailing expedition, perhaps to explore remote islands, coastal regions, or offshore destinations.6. Navigation and Seamanship Course: Enroll the sailor in a comprehensive course focused on navigation, seamanship, and maritime skills to enhance their knowledge.7. Sailing Vacation Package: Surprise the sailor with a pre-arranged sailing vacation package to a sought-after sailing destination, complete with accommodations and boat rental.8. Historical Tall Ship Cruise: Offer an unforgettable experience aboard a historic tall ship, allowing the sailor to appreciate the romance and tradition of sailing.9. Marine Wildlife Watching Tour: Arrange a marine wildlife watching tour, providing the opportunity to observe and learn about local sea life while sailing.10. Sailing Equipment Upgrade: Gift a voucher for a professional boat upgrade, such as new sails, navigation equipment, or safety gear, enhancing the sailor's sailing experience.
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! For as little as $3/month it really helps!
Well, I have a dirty secret to share this week... Ugh. Enjoy! Don't forget to check out my Patreon page a ! Thanks for the ongoing support!
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 Penny
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.
This week I am trying out a few new things including a video podcast. Yikes. Today I am giving you some tools, skills and books to check out to kick off 2024 on the right foot. Here are a couple book recommendations, an essential knot recommendation, sail trim thoughts and docking maneuver to master. Enjoy!
Alright we are finally wrapping up our Sail Series!! Talking about types of fabrics used for sails as well as different cuts that your sailmaker may suggest depending on your sailing goals. Enjoy!
This week I am talking about my process to find a match made in heaven! Finding the right sailmaker can go a long way. I have seen many sailors spend a lot of money and end up with so-so sails. Not good!
coming soon!
This week I am diving into all things sails! I talk about: - different foresails - sail parts - typical wear spots - basic checks to perform regularly - best practices to help keep your sails in good working order Will continue with more info next week too! Enjoy!
I have been MIA for a little bit as Spindrift has been keeping me on my toes! I fix one thing, and 5 more break requiring my attention. I have not been following my own advice and I have been caught up in the weeds! No more I say! So this week I sat down, wrote a list, and came up with my strategy. This is nothing new for me as I am a list queen. But thought I would share some of the thoughts around creating some resilience in the world of boat maintenance... 1. prioritize 2. brainstorm solutions 3. dooms day planning 4. adapt & fix 5. reflect, review and appreciate See you next week!
Coming soon!
Coming soon
Coming soon