Sailboat Days around Vancouver Island & The Gulf Islands
A quieter place to think, learn, and breathe
Some decisions refuse to be made in boardrooms, cafés, or home offices. The noise follows you in: email, markets, news, family logistics, unfinished work.
My sailboat on Vancouver Island exists as a different kind of room. No slides. No audience. Just a classic blue-water boat, cold clear water, coastal mountains, and enough quiet to hear yourself think again.
You do not come aboard to perform. You come aboard to pay attention.
Why a sailboat, and why here
A small, seaworthy boat is unforgiving in the best sense. The sea does not care about your résumé, your title, or your compensation. It cares about weather, weight, balance, systems, judgment and rest.
On deck, there is no “back office” and no way to delegate awareness. If you are cold, tired, distracted, or careless, the elements will point that out without malice and without delay.
That is one reason I chose this life for a while. Moving onto a classic Tayana on Canada’s hauntingly beautiful and dangerous west coast after years of global finance forced a reset: health first, alertness first, real rest first. Sailing solo among the Gulf Islands and Georgia Strait, I learned that staying alive and calm is a full-time discipline, not a weekend hobby. Reading 150-odd books and giving up alcohol, risky motorcycling and “heroic” skiing all came from the same place: a decision to stop outsourcing my well-being to luck.
Many professionals I work with are built like that boat: quietly over-engineered, capable of far more than the conditions usually demand, carrying stress in silence. Time afloat lets you feel that in your own body instead of just thinking about it.
Where this actually happens
The boat is based in Sidney near Victoria, within reach of the Gulf Islands and sheltered coastal waters. Most days happen from late spring to early autumn, when light, weather, and sea conditions are kinder and there is more margin for thinking as well as learning.
We choose routes and ambitions to suit you, not to impress anyone: a short hop across to a quiet anchorage, a day weaving through the islands, or simply staying close to home harbour while we work on fundamentals and talk. The point is not miles. The point is time and attention.
Safety first, always
Nothing about these days is cavalier.
They are alcohol-free and deliberately conservative. We plan around tides, forecasts and daylight, and adjust the plan if conditions tighten. You do not need to be an athlete, but you do need to be honest about your health, fitness, and comfort in and around water. For scuba diving, a current medical sign-off and existing certification are non-negotiable.
The Rescue Diver course I took years ago left a permanent mark: one victim must not become two. That lesson applied to my fresh divorce, to leaving misaligned work, and it applies on the water. The aim is simple: you step aboard; you come back to the dock a little tired, a lot clearer, and in one piece.
What a day can look like
No two days are alike, but the rhythm is steady.
You arrive at the dock. We walk through the boat, systems, safety, and the plan. You are never treated as ballast. If you want to learn, you learn by doing: lines, fenders, basic navigation, helm work in calm conditions, reading the water and the sky. If you prefer more time to think and talk, we trim the day that way instead.
There are no shouted orders. I am not the archetypal skipper who barks to feel powerful. Years of watching ego-driven instructors in dive shops and on boats convinced me there is no wisdom in that. My style is patient, calm, explanatory. You are encouraged to ask questions, to try, to make small mistakes in safe conditions and understand what they mean.
Below deck and at anchor, the conversations deepen. We look at the long-range decisions you are carrying:
a career that has narrowed around credentials and obligation
a move between cities or firms that cannot easily be undone
succession and stewardship questions for a practice, a team, or a family
a midlife shift you can’t explain to people who prefer stability to honesty
Sometimes we also talk about the sea itself: what it takes to buy and run a boat without being sold fantasies, what good seamanship looks like, what ethical orca encounters feel like when they arrive as a gift and not a chase. You can also use the day to brush up on scuba skills with someone who is PADI-qualified, cautious, and has no gear to sell you.
How this fits with the rest of the work
For most people, a day on the boat is not a one-off escape. It is a moving extension of our conversations on land.
Big career decisions, stewardship and succession, “life after 45,” regulatory or professional shocks, questions about suitability of city, firm, role or lifestyle: these are hard to think through while half your brain is grinding on email. The hours under sail or at anchor create just enough distance that patterns show up more clearly.
We do not treat the boat as magic. It does not fix anything. What it does, reliably, is loosen knots. You go back to Toronto, London, Singapore or wherever you live a little less numbed, with a quieter nervous system and a clearer sense of what deserves a yes, what deserves a no, and what deserves more time.
Who this is and isn’t for
This offering is for professionals who are already serious about their lives and work, and who are curious about what emerges when you remove the usual distractions.
You might be:
visiting Victoria or Vancouver for work or holiday and want to pair rest with reflection
a mid-career or later-career professional who feels the ground shifting under them
someone who loves the idea of the sea but has been put off by yelling skippers, macho sailing culture, or dive shops that felt more like sales floors than schools
It is not for thrill-seeking, content creation, or “bucket list” adrenaline. If what you mainly want is Instagram footage, a rush, or a captain to bark orders so you can feel pushed, this will not suit you. If you want a calm and honest day to think about serious things while learning enough about boats or water to respect them, we will probably get on well.
Hope, humour, and the long view
When life is complicated, it is easy to forget that joy and absurdity still exist. Out here, they tend to show up in small ways: the slap of a seal, the sudden appearance of orcas off the bow that we never chase, only watch; a badly made cup of coffee that tastes perfect anyway; the way a quiet bay at dusk makes your full calendar feel less ominous.
We do not treat your situation lightly. But we also make room for laughter, for the oddity of lawyers arguing over commas while the tide comes in regardless, for the sheer privilege of waking up alive in an era as strange as this one. The goal is not to erase scars. It is to help you carry them without letting them define the rest of your story.
How to explore this
Sailboat days are rare by design. Weather, tides, my own schedule between Toronto and Vancouver Island, and your reality all need to line up.
If the idea of working this way quietly resonates, mention Vancouver Island or “sailboat day” when you write to me. We start, as always, with a conversation on land or online. From there, if it makes sense, we design a day or two on the water that fits your health, your experience, and the questions you are carrying.
No packages. No glossy brochure. Just a classic boat, careful seamanship, and concentrated time to think about a life that deserves to be steered, not drifted.