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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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Penny Caldwell
Penny Caldwell
Knowledge. Confidence. Adventure.
  • Ocean Adventures: Pacific Ocean Facts
    Sailing Stories

    Ocean Adventures: Pacific Ocean Facts

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson One of the things that struck me during our trip is just how small we felt. We were on a 50ft boat that weighed over 26,000 lbs… and yet, when the waves said up, up we went. It made me want to learn more about the Pacific Ocean so…

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  • Ocean Adventures: Casting Off!
    Sailing Stories

    Ocean Adventures: Casting Off!

    ByPenny Caldwell August 24, 2026August 24, 2026

    Repost from July 2018, Sail Nelson July 25, 2018 – Hawaii Yacht Club 21’16.35 N, 156’56.51 W Tomorrow am we cast off and head to Hanalei Bay for snorkeling before our sail across the Pacific Ocean to home! I am very excited to get out on the Ocean and to see how Turnagain performs with…

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  • Ocean Adventures: Who’s Who?
    Sailing Stories

    Ocean Adventures: Who’s Who?

    ByPenny Caldwell August 24, 2026August 24, 2026

    Our trip was fantastic! What an expedition and it was a great experience overall. I thoroughly enjoyed being out in the Big Blue, and I’m already thinking about my next voyage… Our boat… Turnagain is a 50 foot Beneteau Oceanis and she was very well equiped for this trip. This was not her first time and…

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  • Ocean Adventures – Gearing Up!
    Sailing Stories

    Ocean Adventures – Gearing Up!

    ByPenny Caldwell August 17, 2026August 24, 2026

    Repost from July 2018, sailnelson.com So I leave Nelson on Thursday to head to Hawaii for the Vic-Maui boat delivery. I will be bringing Turnagain, 50′ Beneteau, back home to Vancouver! I am doing my last minute prep and packing and thought I would share what I am bringing along… For a trip like this…

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  • Ocean Adventures – Whales, Tornadoes, Lightning… Oh My!
    Sailing Stories

    Ocean Adventures – Whales, Tornadoes, Lightning… Oh My!

    ByPenny Caldwell August 17, 2026September 29, 2026

    Repost from June 2018, sailnelson.com For those of you catching up, I have decided to join my friend Travis on his boat Turnagain to return the boat to Vancouver from Hawaii. I have suddenly come to the realization that our trek across the Pacific Ocean from Hawaii to Vancouver for the Vic-Maui delivery is only…

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  • Morgan’s Pirate Adventure!
    Sailing Stories

    Morgan’s Pirate Adventure!

    ByPenny Caldwell August 17, 2026August 17, 2026

    Repost from May 2018, sailnelson.com The mediocre teacher tells. The good teacher explains. The superior teacher demonstrates. The great teacher inspires. ~ W. Ward I’d like to tell you a story. A story about a boy who wanted to learn to sail, and he would not take no for an answer… his name is Morgan….

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  • Sails – Final Steps
    Boat Maintenance

    Sails – Final Steps

    ByPenny Caldwell August 17, 2026August 17, 2026

    “I’m a cheap Scot! I like to know where my money is going, so understanding what I’m purchasing is key.” ~ Sailing According to Coach Penny You’ve decided it’s time for new sails and you’ve found a sailmaker you trust. Now come the decisions. In the final episode of my Sails Series, we’re talking about…

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  • Sails – Finding a Sailmaker
    Boat Maintenance

    Sails – Finding a Sailmaker

    ByPenny Caldwell August 17, 2026August 17, 2026

    “Because the “best” sail isn’t necessarily the most expensive one — it’s the one that’s right for your boat and the way you sail.” ~ Sailing According to Coach Penny Buying new sails is a significant investment, and choosing the right sailmaker can make an enormous difference in the final result. In Part 3 of…

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  • Sails – DIY Repairs
    Boat Maintenance

    Sails – DIY Repairs

    ByPenny Caldwell August 17, 2026August 17, 2026

    “The important part is also knowing when a DIY repair is appropriate — and when your sail needs professional attention.” ~ Sailing According to Coach Penny You’ve inspected your sails and found something that doesn’t look quite right. Now what? In Part 2 of my Sails Series, we’re talking about sail maintenance and repairs —…

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  • Sails – Damage Prevention & Basic Maintenance
    Boat Maintenance

    Sails – Damage Prevention & Basic Maintenance

    ByPenny Caldwell August 17, 2026August 17, 2026

    “A little preventative maintenance can go a very long way when it comes to sails.” ~ Sailing According to Coach Penny Your sails are some of the hardest-working — and most expensive — pieces of equipment on your boat. In Part 1 of my Sails Series, we go back to basics and look at the…

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