Begin From Where You Are

On the morning of August 30, 2025, Katherine and I left the dock in Vancouver, Canada, novice sailors operating a 23-year-old, 40-foot sailboat. We were sailing "short-handed," meaning just the two of us, without sufficient crew aboard to easily handle all the tasks required to manage a sailing vessel of this size and complexity.

Our goal was to cross the Strait of Georgia, a body of water known for rapid weather changes, powerful tidal rips, gale-force winds piling against heavy currents and tall, choppy waves, roiling the constant, international shipping traffic comprised of cargo vessels large enough to crush us without noticing. Not to mention a healthy population of enormous, barely visible logs, stripped from industrial barges or washed from the gullies and rivers pouring from the mountainous British Columbia coast.

We had taken our first sailing lesson roughly 7 months earlier and had never been beyond the shelter of a bay without an experienced, professional sailor on board. Now we intended to attempt a crossing we'd heard people on the Vancouver docks talk about in serious tones. One boat arrived in complete disarray and the owner told me he'd been bucking against the current, burying the bow in waves, with water constantly flowing over his rails because the strong wind was causing his boat to heel over so hard. He seemed legitimately shaken and it took him a couple of days just to settle down and do things like wash the hardened salt spray from his deck and, you know, comb his hair. I overheard another skipper docked nearby telling his crew that everything had to be lashed extra tight for crossing the strait, because the conditions could change in an instant, no matter the forecast.

Nonetheless, we set forth that August morning and what we encountered was...anti-climatic.

There was not enough wind to sail, the waters were calm and there were no more than a few logs. We glided effortlessly under motor through a clear sunny day over to Silva Bay, a protected harbor on the northeast coast of Gabriola Island.

The truth is I've been a bit dramatic. We expected calm weather and knew we wouldn't likely put the sails up. Weather forecasting is very good these days, especially short-term forecasting. Sailing short-handed isn't particularly unusual or dangerous. So, what we were doing wasn't risky. It also wasn't the romantic, bounding across the waves with full canvas launch to a perpetually epic adventure that I might have fantasized about, but importantly we needed to get the hell off the dock and start going somewhere, anywhere.

After deciding to transform most of our worldly possessions into the form of an old sailboat, we'd spent several months working toward that goal. In a future post, I'll talk about all of the unexpected ways in which buying a boat is harder than you'd think and how being from the United States and buying a Swedish-built boat in Canada from a Japanese Owner and registering it in the Marshall Islands transforms an already surprisingly difficult process into something of a Sisyphean slog.

So the best we could manage in order to begin from where we were, was to make a clean break from the allure of Vancouver, from the spell of trying to keep fixing everything forever, from the luxury of huge noodle bowls at New Fuji in Kitsilano, the endless selection of drybags at MEC, and the friendly, helpful folks at Yacht Sales West.

We arrived to find the "famously roomy" anchorage of Silva Bay positively lousy with private mooring balls, meaning there's actually very little room for anchoring. We found a corner, a bit open to swell and wind coming in from the strait, but with enough room to swing, and got the anchor to set well in two tries. Which seemed fine for our first attempt with just the two of us.

Peering out the portlight windows to treetops rather than a boat-filled marina was glorious, it felt charming to have the occasional sea plan landing nearby, and the sunset washed over me like a warm, extended hug, the kind that's better than just about anything once you get over your own awkwardness.

The following night, the wind did arrive and it brought friends. We were surrounded by lightening strikes and buffeted by 3o knot gusts blistering off the strait and into our corner at the edge of the anchorage. I stood naked in the companionway watching the boat pitch and yaw as heavy chop rolled in about twenty degrees off the wind direction and the sky crackled between inky and electric. But the anchor held.

And by morning, a return to stillness.