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Video Log

Welcome to the Sailing Gypsy Wind video logs! Here, I capture life on the water and on the hard.  Raw, unscripted and real, just like my journey.  No filters, no fancy edits.  Just the honest beauty and the occasional beast of adventure, boat life and figuring it all out as I go.

Meet The Skipper

The day I bought my sailboat Gypsy Wind

Hello, I'm Dianne MacGillivray.  I'm a novice sailor finally facing down fear, depression, and chronic pain; one sail at a time.  I bought a boat named Gypsy Wind to trade in my "hyperventilating lump of mush" era for one filled with freedom, duct tape, and showing up for myself (and others) along the way.

 

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