The long wake of a sailing life

My father, Dave, believed that being on a boat was the best way to spend a day. It didn’t matter where he was or who was onboard. When he was on water, he felt most himself. That sense of purpose, the ease of it, shaped how he lived. It shaped me too.

I didn’t grow up sailing in any serious way. Not at first. But when we moved to Montreal and I was about seven or eight, Dave reconnected with an old friend, Frank. Frank had a sailboat but no regular crew. Dave didn’t own a boat, but what seemed to Frank like all the time in the world. It was a marriage made in heaven. Frank not only let us sail with him, but he also let Dave sail whenever he wanted: mi casa, su casa. That’s how it started.

Eventually, we kids were pulled in as regular crew. There were Monday night races, Wednesday night series, and weekend regattas hosted up and down the river. From the St. Lawrence Yacht Club to the Hudson Yacht Club, every club hosted a regatta once in the sailing season. Frank and Dave would round up a few adults to help, but the rest of the crew was made up of my sisters and me. We weren’t just along for the ride. We were expected to contribute.

If you ever want to learn how to sail, crewing a regatta is a good place to start. Sailing is often seen as a leisure sport, calm and slow-moving. But racing is something else. There’s no room for sloppiness or delay. A regatta crew is a study in precision and presence. Everyone moves just enough, just in time, with eyes on the sails.

Outside the regattas, we did plenty of pleasure sailing too. We knew the Richelieu River and the lakes around it by heart. We sailed in Lake Champlain, the Thousand Islands, and Lake Ontario. Later, we made longer trips, in Florida, and Grenada and the Grenadines. After Dave and Pat (my mother) moved to Grenada, nearly all of my vacations were spent sailing with them in Europe, in the Caribbean, Venezuela, and along both coasts of Canada.

I once took a year-long sabbatical just to sail. We left from Scotland, sailed south to the Canary Islands, and crossed the Atlantic to Grenada. Later, I joined another leg of a different trip, this time from Bermuda to Newfoundland with Daniel, my brother, and Jen, my sister-in-law.

Looking back, it’s clear how much those years on the water shaped me. They taught me rhythm and responsibility, confidence and adaptability. I learned how to read people and the wind, how to prepare for what’s ahead without expecting control. I learned how to work, how to rest, how to listen.

In a few months' time, I’ll be joining a commercial vessel, one of Oldendorff Carriers’ bulk carriers, as part of what I am calling the OC Voyage. It’s a rare chance to go to sea again, in a very different way, and to tell stories that bring together past and present. Being able to go on this journey is definitely the final (or is it a new?) chapter of my life at sea. But it carries the wake of all those earlier voyages.

Before that journey begins, I wanted to begin here. With Dave, and stories of sailing in the past that has followed me all my life.