Where It All Began

Come with me for a walk down memory lane.

It’s 2016.

Our oldest daughter is 20, working, finding her footing, starting her life. Our youngest is 17. We’re nearing the end of a very busy chapter: the one where we’ve almost finished raising our little birdies and are getting ready to let them fly. The chapter filled with early Saturday morning hockey practices, late evening dance lessons an hour away, rushing straight from work into traffic just to make it on time. Out-of-town dance competitions. Hockey tournaments.

We could finally see the next chapter ahead.

The one where things slow down.

Fewer schedules.

Fewer obligations.

More living for the moments instead of racing through them.

Up until then, our dream was simple and very us: leaving city life behind for a house in the country, a decent chunk of land, maybe a small hobby farm. A big garden. Lots of flowers. Space to breathe. A life filled with love, laughter, friendship, and muddy boots by the door. The kind of dream with a white wrap-around porch, rocking gently in a chair as we grow grey… who am I kidding — I’m still in denial that the grey has already started.

That cozy country dream didn’t vanish overnight — but it was challenged.

Tom went on a work team-building trip with his coworkers to the Thousand Islands. Sailing. Just for a week. No big deal… or so I thought. He came home completely smitten. Head over heels. Talking about sailboats, winds, destinations, and something called blue-water sailing, which, even to this day, still scares me. Suddenly he wasn’t just dreaming about retirement. He was talking about owning a sailboat, sailing south for the winters, maybe even sailing around the world. Retiring early.

I couldn’t imagine retiring early — or even affording retirement. It felt like the credit cards still had child sports payments on them.

I’m part dreamer, so I humoured it. What’s the harm in dreaming, right? I imagined winters in the Caribbean: no snow to shovel, no ice to tiptoe across, no frozen fingers or toes. No hibernation. Just sunshine reflecting off calm water, anchored near a quiet island. Fishing. Exploring. Snorkeling. A little escape from reality every winter. And honestly… who couldn’t get behind that dream when you’re not exactly fond of Canadian winters?

But instead of fading with time, the dream grew stronger.

Bigger.

Louder.

And if I’m being honest… a little obsessive.

Tom researched boats relentlessly. Watched videos. Read forums. Compared boats. I had the distinct feeling he had our entire retirement mapped out in his head — and I hadn’t even agreed to step on a boat yet.

Fast Forward to 2019.

After three years of listening to him talk about buying a sailboat, he finally came to me with a plan that technically fit into our very non-existent budget. He wanted a Shark 24; and he already knew where he would get it. There’s a charity in Kingston where people donate their boats, and the proceeds of a boat sold go toward a youth outdoor adventure sailing program.

How could I say no?

I had absolutely no idea what I was agreeing to when I finally did.

I probably should have known what kind of season it would be when, before we could even tow her home, we had to rent a truck and buy new tires for the trailer. We didn’t know what we were doing — not even a little bit.

We almost made it home.

Almost.

At a busy intersection, right as people were rushing home from work, the trailer hitch failed. As we braked, the boat trailer bumped the truck — not gently. Chaos erupted. Cars zoomed around us. Horns blared. People shouted. No one seemed to care whether it was safe or not. Thank goodness we had taken out the extra insurance. The rental company handled the truck, and a tow truck came to rescue the boat.

That probably should have been my moment.

The moment where I said, This is too stressful. This boat dream is over. Walk away.

But I didn’t.

Instead, we restored her. We launched her. And we rode the emotional rollercoaster that was our Shark 24.

Tom loved every single minute of that sailing season. I’ll admit that by the end of the summer, he was mastering sailing the Shark — but don’t tell him I said that.

Me? Not so much.

I hated the heeling — and oh boy, could the Shark heel. She was speedy, sassy, and determined to test me. There were no comforts. No bathroom. No real place to sleep. Barely enough room to move. Friends onboard meant pretending personal space wasn’t a thing.

Let’s just say… this was not my idea of a relaxing pastime.

From trailer issues to wind problems at haul-out, nothing ever seemed easy. We had haul-out booked for mid-October, but Mother Nature had other plans. Too windy. Postponed. Then postponed again. By early December, ice was forming and snow was piling up. Tom braved the motor across Lac Deschênes to the Nepean Sailing Club on a bitterly cold winter day to finally get her hauled out.

That adventure? Definitely not for me.

When COVID hit the following summer and the club closed, I quietly breathed a sigh of relief, and pretended to feel disappointed about missing a sailing season. The next summer, the club reopened, but we bowed out again.

That summer marked the beginning of Tom’s PTSD journey — a chapter that deserves its own space and its own telling. We promised the club we’d be back the next summer… and we were, with our Chrysler 26.

But this…

This is where our sailing story truly began.

⚓💙