Dreaming the Voyage Before We Sail

Planning, fearing, and falling in love with the unknown, one nautical mile at a time

Before the first nautical mile is ever sailed, it is imagined.

As our beloved sailboat, Agra2, enjoys her long winter’s nap on the hard (stored out of the water for the season), I find myself not at the helm, but at my office desk, snuggled in my favourite blanket, hot chocolate warming my hands.  I’m surrounded by the tools of my imagination: Waterway Guides spread open like treasure maps, Navionics casting its glow from my tablet, and a seemingly endless parade of browser tabs across my computer.

This is where the real launch point for our next adventure begins.  Long before lines are cast off or sails are hoisted.  Here, in the quiet of winter, the journey is first born as a dream.

Not with the sound of halyards or the scent of salt air, but with quiet moments of dreaming, worrying, planning… and yes, dreaming some more.

I’m currently charting a voyage that will take us from Iroquois, Ontario, a small town on the St. Lawrence River, to the Canadian East Coast: Newfoundland, Nova Scotia, Prince Edward Island, and the French islands of Saint Pierre and Miquelon. Tom supports my planning by dropping recommended anchorages and marinas into Google Maps so I can begin connecting the dots.  It’s part puzzle, part research, part hope and very much a leap of faith.

If I’m being honest, my heart would be perfectly content with another season of slow summer days in the Thousand Islands: iced tea in one hand, book in the other, floating beside Agra2, watching the world drift by.  Sprinkle in time at our yacht club with our yacht club fam, a dash of visits from friends and family, and my version of paradise is complete.

But here’s where our story gently shifts.

Tom’s dreams don’t stop at our trip out East or even in the Caribbean.

What began as visions of us becoming sailing snowbirds has expanded into dreams of heading north to Greenland and Iceland, then on to Ireland and beyond.  My mind, of course, immediately screams: Icebergs! Titanic! No Thank You!

And in moments like these, I have to admit that I need baby steps.

Very sweet, cautious baby steps, if I’m going to keep moving forward with our shared dream.

So eastward first.  The St. Lawrence River will carry us to the Gulf of St. Lawrence, then out into the Atlantic Ocean.  Maybe one day, the Caribbean.  Let’s see how I do.  I remind myself that with baby steps, we can always adjust course or even turn back if needed.  That’s the comfort in starting small.

We’re choosing now over someday.

And when I need to slow down, we can always return to the gentle rhythm of Thousand Islands life; my safe harbour.

Maybe it’s the adventurer in me, but I’ve always loved seeing the world from a different perspective.  I’ve travelled coast to coast across Canada, wandered throughout the U.S., explored much of England, and vacationed in Scotland and Mexico.  I’m the one who always insists on the window seat, not just to arrive, but to witness the journey.

To me, sailing is the ultimate window seat, only slower, deeper, more intentional.

It’s not about the destination.It’s about the way the world reveals itself to you along the way.It’s about how each moment becomes part of a story you didn’t know you needed.

And oh, what a world I’m dreaming about.

Kayaking at sunset. Lighthouses emerging from the mist. Small fishing towns filled with history and stories. Fish and chips. Foggy mornings. Gentle coastlines. Sun on your face, wind in your hair kind of days.

I’ve lost count of the hours I’ve spent watching YouTube videos of sailors who’ve gone before us with whales surfacing beside their hulls, dolphins dancing in their wake. I still remember the magic of walking along Nova Scotia’s cliffs, watching waves crash against the rocks.  But imagining those same waves from Agra2’s deck? That’s a whole different kind of awe, tinged with fear, but still irresistible.

Still, I can’t stop picturing it: sailing with whales as our neighbours, exploring from our “big” little floating home, slipping off the swim platform into my kayak, or floating beside the boat on slow, quiet afternoons.

And that’s what this is really about.

The experience. The memories we’ll create. The privilege of being together.

But dreams and reality are two sides of the same coin, and planning this trip is no small feat.

Looking back, we’ve sailed for five seasons now; the Ottawa River, the Great Lakes, and the Thousand Islands.  And yet, there’s a part of me that still feels like a newbie, standing at the edge of something vast and unknown.

The St. Lawrence will be our first real dance with strong currents, tides, swells, and eddies.  There are marinas we’ll only be able to enter at high tide, stretches where the current could actually push Agra2 backward, and bridges where we’ll need to remember to start the engine or risk being nudged where we don’t want to go.

And then Out East… that’s a whole different world.

Ocean weather. Fog. Fewer marinas. More exposed anchorages. Bigger water. Bigger unknowns.

Out there, we’ll be relying much more on anchoring—and that still scares me.

And yet—somehow—we’re doing this.

And then there’s Newfoundland.

Tom dreams of retracing history along the Viking Trail, visiting the Viking museum, standing where history once stood. I want that too, but I haven’t yet found a route that makes me feel safe enough to say yes wholeheartedly.

It’s here that our differences come into focus.

Tom plans from possibility; I plan from caution. Where he sees opportunity, I see risk. He’s optimistic; I’m realistic, maybe too anxious.

Just the St. Lawrence alone could take us three to four weeks or more, depending on weather, currents, and tides. We have to balance time on the East Coast with the need to return to Iroquois by the end of September or head south for winter.

It’s terrifying. We will be sailing in an ocean.

And thrilling. And magical. And overwhelming.

Our teamwork is tested and strengthened during evening conversations in the hot tub that often double as therapy sessions.  Tom listens to my fears.  Together we problem-solve, draw from lessons of past journeys, and remind each other why we’re doing this.

Compromise becomes our anchor. Trust becomes our wind.

Because despite all the worry, I love to travel and connection pulls me forward.

I love discovering new places. I love meeting amazing people and gathering the kinds of stories only adventure can offer. I love learning the history of where I am.

Planning this adventure often feels like assembling three mixed-up puzzles at once: one for the ideal plan, one for the backup plan (and maybe a backup for the backup), and one for the “oh no” emergency escape plan.

Every anchorage, every marina, every stretch of open water is scrutinized, marked, and reconsidered.

And honestly? The planner in me is doing a happy dance.

For the first time in two years, I’m able to start plotting our life again and that feels wonderful.  The sense of forward momentum is deeply welcome.

We’re investing in ourselves too: navigation courses, weather reading, learning the secrets of tides and currents. Because loving adventure doesn’t mean ignoring preparation.

It means respecting every challenge along the way.

I want this journey to be meaningful. Time together, free of outside distractions. I want it to be safe. A rhythm with the wind and tide. I want it to be full of exploring, laughing, resting not rushing. I want the stories I don’t even know how to imagine yet.

A journey of sailing with love, through fear, through wonder, through the vastness of the unknown, and through the in-between.

So here I am, dreaming of peaceful sailing, kayaking, whales, and lighthouses, nervously tracing routes with my mouse, and reminding myself again and again:

Every great adventure starts exactly like this.

With a little bit of fear. And a whole lot of love.

🩷🌸

The Plan so far .....