
#83 Mastering Winches: A Sailor's Guide!
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 signi...
1 Feb 19min

#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 yo...
19 Jan 21min

#81 Am I ready for the Intermediate Bareboat Sailing course?
SummaryIn 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 pri...
5 Jan 21min

#80: Three Generations, One Boat: A Sailing Story
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 episod...
29 Des 202533min

#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...
23 Des 202517min

#78 Croatia 2025 Trip & Highlights!
SummaryIn 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 ...
27 Nov 202526min

BONUS: AI hosts discuss Bareboat Cruising course in Desolation Sound
Bonus episode created with Google Notebook LM.
27 Jan 202515min

#77 Creating an Itinerary! The basic steps...
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?
27 Jan 202529min



















