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Penny Caldwell

Penny Caldwell

Knowledge. Confidence. Adventure.

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    • Podcast Series: From Passenger to Confident Skipper
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Penny Caldwell
Penny Caldwell
Knowledge. Confidence. Adventure.
  • When Things Go Sideways: Staying Calm Under Pressure
    Sailing Skills & Seamanship

    When Things Go Sideways: Staying Calm Under Pressure

    ByPenny Caldwell September 29, 2026September 29, 2026

    “When things start going wrong on the water, your greatest asset isn’t speed—it’s your ability to slow the situation down.” ~ Sailing According to Coach Penny Every sailor eventually has one of those moments. The docking approach isn’t working. The wind suddenly picks up. The engine won’t start when you need it. A crew member…

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  • Seasickness!!
    Sailing Skills & Seamanship

    Seasickness!!

    ByPenny Caldwell September 10, 2026

    “Seasickness can ruin a day—but planning ahead can make a huge difference.“ ~ Sailing According to Coach Penny If you know you are prone to seasickness, make your prevention plan before departure. Once you are already sick, every solution becomes harder to manage. What You’ll Learn Seasickness is incredibly common, and it does not care…

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  • Which Sailing Course Do I Take?
    Sailing Skills & Seamanship

    Which Sailing Course Do I Take?

    ByPenny Caldwell September 10, 2026September 10, 2026

    “Choose a course based on what you want to be able to do after it – not simply the next certificate in the sequence. Your sailing goal should drive your training plan.” ~ Sailing According to Coach Penny So you have decided you want to learn to sail—fantastic. The next question is usually, ‘Which course…

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  • Safety First! What Safety Gear Do You Need?
    Safety

    Safety First! What Safety Gear Do You Need?

    ByPenny Caldwell September 10, 2026September 10, 2026

    “Keep your emergency gear together and easy to reach. A beautifully stocked locker is no help if nobody onboard knows where the equipment is.” ~ Sailing According to Coach Penny Safety gear is one of those subjects that can quickly turn into a giant checklist. Regulations matter, of course, but I want sailors to think…

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  • New Sailor Sailing Gear – Do I REALLY Need That?!
    Sailing Gear

    New Sailor Sailing Gear – Do I REALLY Need That?!

    ByPenny Caldwell September 4, 2026September 10, 2026

    “Do not build your sailing kit all at once. Start with what you already own, get on the water, and let your actual sailing tell you what is worth upgrading.” ~ Sailing According to Coach Penny When you first get into sailing, it is very easy to believe you need an entire closet of specialized…

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  • Ocean Adventures: The Commandments of Ocean Sailing
    Sailing Stories

    Ocean Adventures: The Commandments of Ocean Sailing

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson As I complete my thoughts about our trip, I have realized that there are some basic rules and things to know before heading off on a trip like this. Here I shall share them with you. My commandments of offshore sailing: Hope you enjoyed our journey and you have…

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  • Ocean Adventures: Heading Home
    Sailing Stories

    Ocean Adventures: Heading Home

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson Aug 11 2018 – 48’7.33 N, 126’8.77 W Today is Geoff’s birthday! And no one will let him forget it for a minute! Ha. Sound familiar? We have decided we are living groundhog day every shift. We have a “routine” of get up, get food, get dressed, look for…

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  • Ocean Adventures: Sneaky Simon
    Sailing Stories

    Ocean Adventures: Sneaky Simon

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson Aug 7 2018 – 41’30.67 N, 140’32.32W Today is my birthday and no one will let me forget it for a minute! Nope. Every time I get up for shift someone yells “Happy Birthday Penny!”. Ha. The first few times I felt really special and spoiled… now I have…

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  • Ocean Adventures: Privacy Issues
    Sailing Stories

    Ocean Adventures: Privacy Issues

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson Aug 3 2018 – 37’8.60 N, 152’44.60 W So we have lost the door to our head. Poor Turnagain is getting pretty beat up on this trip and I can’t help but feel for Travis as he tries to manage all of us and our “intricacies”. I have been…

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  • Ocean Adventures: This too shall pass…
    Sailing Stories

    Ocean Adventures: This too shall pass…

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson July 30, 2018 – 28’10.6 N, 158’28.08 W We have been on a starboard tack for 4 days now. I don’t remember what it feels like to stand on solid ground and my hips are bruised from bracing myself against the counters and tables whenever I walk around inside…

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