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2026 Week-Long Cruise: Gusty Winds, Gear and Good People
Gusty winds. Cool mornings. New friends. And a motor that finally lifts. My first week-long cruise of 2026 was an adventure I won't soon forget.

Dianne MacGillivray
4 days ago3 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


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


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
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