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Why I Sail And Write About It
Sailing didn't just teach me about wind and waves. It taught me how to breathe again. It isn't easy to put into words how it changed my life. This is a story of how a sailboat became my therapy, my teacher and my path back to myself and why I'm sharing it with you.

Dianne MacGillivray
Sep 26, 20253 min read


State of the Union Tour 2026
The 2026 sailing season is almost upon us here in Atlantic Canada. Like most boats, Gypsy Wind and I are starting to prep, slowly, messily, and with duct tape nearby.
My 2026 dreams and schemes are already swirling in my head. But before the real work begins, here's a bare-bones, no-frills tour of her interior. A little sneak peek at the "before" — the projects I've got planned for this year.

Dianne MacGillivray
May 221 min read


2026 Spring Commissioning on a Budget and a Prayer
As boat owners know, there's always something that needs doing before launch. In my case, lots of somethings. Seasonal maintenance. Replacement projects and the usual 'why did I start this' job. Our boat club has two spring launch dates. I normally take the later one, as I’m usually such a hot mess and never ready, but I realized, I’ll probably never be ready for either launch. So, I’m aiming for the early one. Which means, I need to hustle this spring, once it’s warm

Dianne MacGillivray
Apr 275 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


What Happens When Women Take the Helm?
From trying to be invisible at work to finding my voice at the helm. How sailing with other women gave me confidence, friendship, and a place to belong.

Dianne MacGillivray
Mar 214 min read


Pine Island, Washademoak Lake: Fog, Feathers and a Falcon Family
A misty morning. A paddle to Pine Island. A severed bird leg on the shore. What I found there became more than a mystery. It became a reminder that not every secret needs to be solved. Some are just meant to be witnessed.

Dianne MacGillivray
Mar 12 min read


Is Sailing a Metaphor for Life? (Yes, and Here's How)
I've spent years drifting, a sailboat without wind, without a hand on the helm. Then I started sailing. Slowly, I realized: I wasn't just learning to handle a boat. I was learning to handle my life.

Dianne MacGillivray
Feb 202 min read


The Invitation That Changed Everything
How a week with a woman sailor rekindled a dream I thought I'd drowned.

Dianne MacGillivray
Feb 53 min read


Enter Cujo
Sometimes opportunities show up in the most unexpected ways.

Dianne MacGillivray
Jan 172 min read


2025 Sailing Season
Reflection of 2025 Sailing season - Highs and Lows (I mean learning opportunities!)

Dianne MacGillivray
Dec 26, 20253 min read
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