In the beginning, there is usually a dream… in this case, there was a dream of clear blue waters, crisp white sails, wide horizons, and unspoiled tropical islands. The only thing that stood in our way was the boat. Or lack thereof.
Sailing off into the sunset starts with, perhaps, the most practical action of all: buying your first boat. I suppose you could say that the true beginning of buying our first boat happened at a Christmas Party. For us, it was one neighbourhood get-together that really got the booze-infused snowball rolling.
Our Secret Santa Street Party was coming to a close, and I’d ended the night with a retractable camping lamp. Not a bad haul, but our neighbour Pirate Bill (aptly named, I assure you) insisted that my lamp would be the perfect addition to his boat. After having missed out on the Himalayan salt shot glasses and the waterproof bluetooth speaker, I was pretty satisfied with my third-rate prize but there’s always that someone who just doesn’t give up, right?
Cue the on and on and on (and on) about just what an asset this lamp would be to those nights on the mooring ball.
Okay, fine, whatever. I’ll trade you my gift for yours… and a sail once summer rolls around.
The deal was made. Bill’s prize that night just so happened to be a bottle of cinnamon schnapps, which proceeded to be passed around (and around, and around). The bottle never made it past the party (even though the memory lingered throughout the next morning), but the sail was penciled in.
Fast Forward to Sailing Season
So it was that shortly into the spring sailing season, Don and I found ourselves on a sailboat together for the very first time. There was no wind and the lake was as still as glass, but the sun was shining, the beer was cold, and there was an air of freedom that seemed a world away from the claustrophobia of the city.
Up until this point, we’d been doing a lot of talking about sailing, and had the ambiguous someday dream of buying our own boat and making our way around the world. The talk always flowed pretty freely, but there was never any actual movement toward buying our first sailboat.
It wasn’t until that moment, while bobbing around on Lake Ontario in a non-existent June breeze, that we came to our senses.
This was a view we wanted to get used to.
Why on earth are we waiting for someday?
I think we started shopping that night. Sifting through brokerage websites and sale-by-owner ads online, it turns out that Toronto is a great place to buy a boat. Opportunity abounds in each and every harbour (and there’s a lot of them).
In order to focus the Great Sailboat Search, we narrowed down our research field to just three very basic (because it’s hard to get technical when you have no idea what you’re doing) key points. Those points were:
- Price
- Location
- Size
We set ourselves a modest budget and singled out boats home to our most local sailing clubs in East Toronto. The size parameters were aligned relative to our experience (minimal) and allotted expenses (also minimal).
Within days we were off to view our first boat (then our second, then the third) and, as it had been made abundantly clear so far in the process that we were absolute amateurs, we brought along the number one (and, it should be noted, only) sailing resource we had: Pirate Bill.
One Boat, Two Boat, Red Boat, Blue Boat
There was a Bayfield that was still suspended in its cradle on the hard well into July, with the wood peeled back far enough that one might be led to wonder if she’d stuck her mast in an electric socket.
There was the O’Day, nestled below the cathedral cliffs of Scarborough. Her skipper admitted that he knew less about the boat itself than he knew about sailing. While it was a level of knowledge that we were currently in no place to contend with, the boat smelled like a soggy sponge after too many days in the kitchen sink and there were spots along the deck that felt pretty similar.
Tired of being dragged along to wince at floating lemons, Pirate Bill decided to take matters into his own hands. In the sailing world, especially in the DIY sailing world, you’ll usually find that you know a guy who knows a guy. Bill just so happened to know a guy.
We Meet Highland Fling
On a sunny day toward the end of July, Don and I were introduced to Highland Fling, and in an instant we just knew that she was the one. Twenty-six feet of perfection, she ticked all of the right boxes. Spacious on deck, in the cockpit, and able to sleep our family of four with room to spare. Tick, tick, tick. An impressive selection of crisp sails, a hull that had been meticulously refinished, and a salty skipper with ready answers to every question. Tick, tick, tick.
When you fall into that revery of puppy love, you fail to notice flaws of any kind. Over time the honeymoon glow starts to fade and certain aspects of your loved one become apparent as, shall we say, less-than-perfect. It took until the next season for us to start to lament not having a stable head, or holding tanks, or running water. The absence of an antenna, or mast lights. And we don’t even recall noticing during those first few weeks of courtship that somebody had started to scrape the paint from the cockpit, leaving the deck a pockmarked mess.
No, in those first few viewings of Fling, we were hooked. We played the back-and-forth marketplace game over the course of the next couple of days, and were soon thereafter able to call ourselves boat owners. We had just succeeded in buying our first sailboat.
Where Do We Go From Here?
We asked Pirate Bill what we should do now. The pointy end of the boat goes first, which may or may not be the best advice we’ve had so far.