Your Pocket Sailing Instructor

Your Pocket Sailing Instructor

By Penny Caldwell

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
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01/19/26

#82 Equipment Upgrades! NOW is the time!!

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 … Read more

01/05/26

#81 Am I ready for the Intermediate Bareboat Sailing course?

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 certificati… Read more

12/29/25

#80 Multi-generational Sailing Trip!

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 … Read more

12/23/25

#79 Last Minute Christmas Gift Ideas!

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 i… Read more

11/27/25

#78 Croatia 2025 Trip & Highlights!

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 saili… Read more

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