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Penny Caldwell

Penny Caldwell

Knowledge. Confidence. Adventure.

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    • Series: From Passenger to Confident Skipper
    • Series: All About Sails!
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  • About Penny Caldwell
Penny Caldwell
Penny Caldwell
Knowledge. Confidence. Adventure.
  • From Impulse to Informed: Graham’s Boat Buying Journey
    Podcast Episodes

    From Impulse to Informed: Graham’s Boat Buying Journey

    ByPenny Caldwell August 12, 2026August 13, 2026

    “The first boat teaches you what the second boat really needs.” ~ Sailing According to Coach Penny Buying a first sailboat is exciting – and it can also be a crash course in research, maintenance and discovering what you actually value aboard. Today I chat with my instructor and friend Graham about his path from…

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  • SailTies: Turning Every Voyage Into a Story
    Podcast Episodes

    SailTies: Turning Every Voyage Into a Story

    ByPenny Caldwell August 12, 2026August 13, 2026

    “A modern way to log your sailing, build your sailing resume and connect with the right crew.” ~ Sailing According to Coach Penny Paper logbooks have their place, but sailors now have new ways to record experience and connect with one another. I sit down with SailTies co-founders Chris and Tom to explore an app…

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  • Standing Rigging 101: What to Check Before it Fails
    Podcast Episodes

    Standing Rigging 101: What to Check Before it Fails

    ByPenny Caldwell August 12, 2026August 13, 2026

    “Your standing rigging works hard every time you sail – give it a proper look before it gives you a problem.” ~ Sailing According to Coach Penny Standing rigging is easy to take for granted because much of it simply sits there doing its job – until something starts to wear, crack or loosen. In…

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  • snowy winter scene at dutch canal
    Podcast Episodes

    Winterizing! How to winterize your sailboat

    ByPenny Caldwell August 12, 2026August 13, 2026

    “Protect the boat now so spring commissioning is a whole lot happier.” ~ Sailing According to Coach Penny Winterizing a sailboat is not quite the same for every boat – or every storage situation. In this episode, I discuss two boats at once: one staying in the water and one stored on the hard. I…

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  • grayscale photo of a tilted sailboat on shore
    Podcast Episodes

    Desolation Sound Mayday!

    ByPenny Caldwell August 11, 2026August 13, 2026

    “A real Mayday call is a powerful reminder that seamanship includes knowing what to do when someone else is in trouble.” ~ Sailing According to Coach Penny During a summer trip in Desolation Sound, my crew and I overheard a Mayday call – the kind of radio traffic every sailor hopes never to need but…

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  • Creating an Itinerary! The Basic Steps…
    Podcast Episodes

    Creating an Itinerary! The Basic Steps…

    ByPenny Caldwell August 11, 2026August 13, 2026

    “A good sailing itinerary gives you a plan – and enough flexibility to change it.” ~ Sailing According to Coach Penny Planning a sailing trip is about much more than drawing a line between marinas. I break down the basic process I use to build a sailing itinerary, including how to research a destination, think…

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  • Croatia 2025 Trip & Highlights!
    Podcast Episodes

    Croatia 2025 Trip & Highlights!

    ByPenny Caldwell August 11, 2026August 13, 2026

    “A return to Croatia – this time with more space, more relaxation and a very different kind of sailing trip.” ~ Sailing According to Coach Penny I returned to Croatia for another sailing adventure, but this trip looks quite different from my previous visit. This time around I had a Lagoon 42 catamaran and I…

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  • Three Generations, One Boat: A Sailing Story
    Podcast Episodes

    Three Generations, One Boat: A Sailing Story

    ByPenny Caldwell August 11, 2026August 13, 2026

    “Having four generations on one boat is not something many people get to experience. My heart is full with this family sailing trip!” ~ Sailing According to Coach Penny What does it take to put four generations of one family aboard a sailboat and make the trip enjoyable for everyone? I share the story of…

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  • Am I Ready for the Intermediate Bareboat Sailing Course?
    Podcast Episodes

    Am I Ready for the Intermediate Bareboat Sailing Course?

    ByPenny Caldwell August 11, 2026August 13, 2026

    “Before you step aboard for an intermediate course, make sure your skills, experience and expectations are ready too.” ~ Sailing According to Coach Penny Wondering whether you are ready to move beyond basic sailing and take an intermediate live-aboard cruising course? I walk you through the experience, knowledge and preparation that will help you get…

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  • Chartering Step 1 – Choosing a destination
    Podcast Episodes

    Chartering Step 1 – Choosing a destination

    ByPenny Caldwell August 11, 2026August 13, 2026

    “I like to research my sailing charter destination by asking other sailors! Where have you charted before? Why did you choose that destination? What did you like about it? “ ~ Sailing According to Coach Penny This week I’m talking about choosing a sailing destination and the steps that I go through when I’m choosing…

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  • Knowledge Centre
  • Podcast
    • Series: From Passenger to Confident Skipper
    • Series: All About Sails!
  • Sailing Adventures
  • Contact
  • About Penny Caldwell