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Solo Sailing: I went for 4 Days – Stayed for 11
I planned for 4 days. I stayed for 11. My first solo trip on Gypsy Wind taught me that the river has other ideas and that showing up scared is the whole point.

Dianne MacGillivray
Sep 166 min read


The Other F-Word - What I’ve Learned About Failure and Sailing
Failure used to terrify me. Then I bought a boat and failure became my most consistent teacher. Curled halyards, cut wires, and missed moorings. This is what I learned.

Dianne MacGillivray
Aug 103 min read


Spring New Beginnings
This is me, I'm smiling for the camera but in reality that's not how I actually felt.

Dianne MacGillivray
Jul 151 min read


2026 Shakedown Cruise
I braced for chaos. Instead? Sun, thunder, rain, then sun again — and nothing went seriously wrong. My first shakedown cruise was uneventful. And that was everything.

Dianne MacGillivray
Jul 101 min read


A Tale of Two Halyards
I had the boat. I had the river. I had the wind. What I didn't have was a halyard that could actually raise a sail. Two halyards, zero sails, and the friends who saved my season.

Dianne MacGillivray
Apr 83 min read
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