For nearly nine years now—most of my adult life—I have dreamed of sailing and surfing around the pacific. Hawaii, the Baja, Costa Rica; surf breaking in the foreground and my sailboat in the back.

Nine years ago I was an idealistic prairie kid looking for adventure, but I have held onto the dream as my hair has begun migrating south, my back has stiffened, and I have generally passed the age when it was cute to believe in such romance.

This fantasy voyage has begun twice.

Three years ago I sailed out of protected waters in a boat I had been rebuilding for eleven months with my friend Jon. Within 30 hours we were heading back, our spirits humbled and our vessel crippled, after spending an awful night doing emergency repairs, vomiting, and wishing we were home.

I had tearfully left Victoria, and my lover, only a few days earlier. Already failure was mine.

The night the mast broke, operating on no sleep, we learned another meaning of humiliation after losing the paddle for our dinghy in a light windstorm and blowing ashore amid our own search party, consisting of coastguard and a couple of well-meaning, though drunken, fishermen.

It took some two years to forget the experience sufficiently to want to try again. During one of Jon’s rare visits to Vancouver, while his girlfriend was pissing in a restaurant bathroom, we shook hands on a plan to head out a second time. Over the next year, we spent hundreds more hours and thousands more dollars making the boat virtually indestructible. Four months ago I believed all the romance had scoured away, leaving a pragmatic, prepared and confident sailor with an unshakable faith in my vessel and an absolute trust in my mate.

Many years ago, while living in Victoria, I would often skateboard at the Gordon Head skatepark. At the time it was the best in town. Skateparks attract many characters, and Buzz was, and probably still is, a Victoria skateboard character par excellence.

Buzz could skate well, but he was obsessed with a single maneuver: an early-grab 360 over the big pyramid. He would pump over every obstacle in the park, gathering obscene speed, power up the pyramid tucked in a tight ball, then launch, slowly rotating.

He almost always overshot the transition, dropping more than eight feet onto flat pavement. I saw him land the trick only once. Buzz, not known for his mental stability, was usually angry after missing it, angrier for every time he had tried and failed.

The one time I saw him land it, he was furious. He screamed and cursed like a jock on angel dust, throwing his board around the park. Looking on, I was both awestruck and confused.

The second time around, Jon and I sailed out of Bamfield. The trip was totally uneventful, with shifts—four hours on, and four hours off—seeming to stretch for days.

We sailed 240 straight hours. Two weeks ago, Jon and I cruised under the Golden Gate Bridge, completing one of the more difficult and unpredictable crossings in the northern hemisphere.

I have begun to adjust to anticlimax, begun to realize that you dream of moments and live through days, but that arrival in San Francisco was possibly the most disappointing week of my life.