Illustration by Mary Kirkpatrick
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The freshly varnished boat railing glistens in the tropical sun, mirroring the pride in its owner’s eyes as he applies the final topcoat and reminds me to avoid contact for at least an hour or two. He’s stating the obvious, to be sure, but in doing so he also renders it a near certainty that not 10 minutes later I’m gripping the damn thing with my whole palm and several sticky fingers. Hardly the impression I was hoping to make.
As captain, custodian and sometime concierge of the stalwart 57-foot ketch rig sailboat Vagabond, my friend Dan’s work is truly never done. I recently cashed in his open invitation for crew and arrived for a week-long visit during a particularly calm interlude in his grand journey around the globe.
“Crew” does, of course, suggest a contribution beyond the oatmeal and a radio part I brought along from home; it implies a productive role. But as we bob gently off the windless coast of Phuket in southern Thailand – with the sweltering heat closing in, and my claustrophobia acutely boiling up – it quickly becomes clear that my presence might not be additive after all. I’ll need to accept occupying a space closer to dead weight than first mate.
Dan is in the ninth year of what was originally envisioned as a three-year adventure, so he’s got a lot to teach about changing tack and modifying expectations. After dreaming of the moment for 30 years, he was brimming with hope and awash in timelines when he boldly set out from Toronto Harbour on Canada Day back in 2015.
But just a few months in, the master schedule – dictated by weather windows for each leg – was already fraying. He was late getting to the Caribbean, then the ship required a major repair. Three years had suddenly become four. The 39-day Pacific crossing went well, but Fiji to New Zealand was dramatic and traumatic, leading to a year-long stay in the latter. Then two years in Australia sitting out the pandemic, followed by eight months in Bali.
Connecting the dots on a map became more of a guideline than a directive. In time, the sound of the ticking clock was lost on the breeze. I certainly hear no trace of it as we sit gazing out across the Andaman Sea. “From a well-defined trip around the world, it evolved into a lifestyle,” Dan tells me.
The first night, I try sleeping in a pool of sweat belowdecks (there’s no air conditioning, of course, and as far as I can tell, there’s little air to work with in the first place). Each night after that, I pull a thin mattress up top and slumber under the caress of the tropical breeze and the blanket of stars, woken only by the little birds pondering me at dawn.
Dan makes fruit and oatmeal for each breakfast, but otherwise we go ashore for cheap and delicious Thai meals. I swim on a whim. My last morning, while packing up to disembark, I already feel I’m abandoning the seeds of a rhythm.
As for Dan, the longest he’s lived anywhere now is on Vagabond. It’s his home, his transport, his constant ally. He gets land sick when he’s away from it. This is not luxury living, to be sure, but that’s looking at it through a distinctly Western lens.
“I’m probably regarded back home in Toronto as this poor guy who’s lost his mind and lives below the poverty line by Canadian standards,” Dan says. “And yet out here I represent impossible wealth.”
Material wealth comes up often as we chat. “I mean, the poorest people I’ve met on this trip have been the most generous,” he notes. And when he thinks about the people back home – people like me, still diligently scampering ‘round the hamster wheel – he wonders what we feel we’re chasing. “Time is our greatest resource. You can’t make any more of it.”
Another way to measure wealth, of course, is through experiences. And Dan’s have been varied and colourful. He’s also met – and learned from – countless fascinating people along the way.
Some have been locals, some intrepid voyagers like him. Still others have joined him as crew, which is how he recently met the woman who’s changed everything. Because, as fate would have it, I’m visiting Dan during a pivotal moment in his odyssey. He’s now in love, and future plans are no longer solely his to make.
As I stand gently rocking in the hotel bathroom my first night back on terra firma, I find myself musing about freedom, or at least my version of it. My time on Vagabond also got me thinking about dreams, and time itself, and the unflagging pursuit of one to make the most of the other. Parachuting into someone else’s life can nudge you closer to answering some of the bigger questions about your own.
I find out later that there was enough wind that very afternoon to sail back down around Phuket; for the first time in all those years, Dan was quietly sailing away from Canada, heading back to Indonesia to see places he’d missed the first time and share it all with his new companion. And with that, the dots were no longer strung out in sequence. The finish line had evaporated. The journey itself had taken the wheel.
Paul Ackerley lives in Toronto