top of page

2026 Shakedown Cruise

  • Writer: Dianne MacGillivray
    Dianne MacGillivray
  • Jul 10
  • 1 min read

This was my first official shakedown cruise. I'm not usually ready, but this year, I made it!


I'd heard the stories, friends who forgot food, forgot tools, forgot their own rain gear and things not working properly.   I braced for chaos.

 

Instead?  We had blistering sun.  Then thunder, lightning, and buckets of rain.  Then sun again.  Somehow, through it all, nothing went seriously wrong.

 

Three boats.  A mission to have fun.  A three-hour trek to Whelpley's Cove.

Checking our usual waypoints along the way, because sometimes a channel marker buoy drifts over the winter and you don't want to find out the hard way.

 

We grabbed a mooring.  We ate.  We laughed.  We slept.


Mast lights on for the night.  Yes, Mine works!!
Mast Lights On For The Evening - Yes, Mine Works Now!!

 

We moved up river to the outside of Kingston Creek.  More food.  More laughter.  Rinse and repeat.


Boats on the outside of Kingston Creek
Floating just outside of Kingston Creek

Dusk and Twinkle Lights on Boat.
Lovin' My Twinkle Lights

While I was heading home, I realized: an uneventful shakedown cruise is actually the best kind.  It means the boat is ready.  It means I'm ready.


Bundled up on the sailboat
Chilly Trip Home

 

So, here's to the quiet trips.  The ones where nothing dramatic happens and everything goes right.

 

What's your favourite part of a shakedown cruise? Let me know below.

 

Comments


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. You can too.

 

Read More

 

Join our mailing list

© 2025 Sailing Gypsy Wind. Powered and secured by Wix

bottom of page