I’m a Boomer and a sailor. If you’re my age, the first image you have of sailing is Jack Kennedy and a bunch of tow-headed kids on a big cutter, in winds I’d never go out in. I’m what’s known as a wind pussy, scared of anything over 8 knots, 10 knots max. I wrote earlier about my first boat, the Katherine Rose, a modest 22 footer I bought for $5000 on my 50th birthday. I sailed her happily for seven years as a “rubber band” sailor (out and back again). I started to get bored with the regular two hour day sailing.
Then something happened. My wife wanted to get me out of the house more. She suggested renting an office. I said, why not a floating office? We somehow convinced ourselves it made economic sense to buy a really big boat to use as my office, and as our cottage. I knew by now what I wanted. A motorsailer, with both substantial engine power, as well as vestigial sail power. A wheelhouse. A ketch. Lots of wood (not the hull, inside). Solid construction. 
Much research led me to a Finnish motorsailer, the Nauticat 33, built from the 80s until today, very handmade, very crafty, 38 feet long overall. There were two available, one in Chicago and one in Texas. They were in high demand, and these two needed work. Still, it was going to be worth my while to put one of them on a flatbed and get it to Toronto.
Then fate intervened. Just up the lake, 40 miles in the other direction from where my first boat had come from, a clean 1986 model of this boat came on the market. It was more than I wanted to spend, but it was beautiful and well-kept; a previous owner, a German, had obsessively labeled every valve, through-hull, switch and connector in the boat. Every spare part he had ever replaced was still aboard. It was called Passat, or trade wind in German.
I had to sell the Katherine Rose, not so much for the money (after 7 years, she was pretty used up) but to get her off my mooring and out of the club. It’s very hard to dispose of a boat in Toronto, and you’re not allowed to sink it. After lowering the price to $2000 all in, motor, cradle, sails, and getting a couple of nibbles, Manny called me. Manny had long oiled hair,  tattoos of tattoos on his tattoos, and a tattoo of a cross on a chain to go with his cross on a chain. Manny has a set of gold teeth he occasionally wears. Manny is not what you’d call yacht club material, and I think he makes his money in sublegal ways, because he paid me for the Katherine Rose with twenty crisp sequential $100 bills.
I did sea trials with Passat on a day with a 20 knot offshore wind, so we never even hoisted the sails. The next day, delivery day, the wind was just as blustery, and it was right on our stern going back to Toronto. And once again, we set out in a strange boat with a motor we knew nothing about to travel 40 nautical miles to Toronto. I forgot, but this was something I had done with the Katherine Rose and swore I would never do again.  It turned out later, the alternator didn’t work and we were running on the last of our battery power. Passat has an autohelm, which keeps her on a set compass course by hydraulically adjusting the rudder. With 20 knots of wind and 4 foot swell on our bum, we were being swung all over the place, and the autohelm was working overtime to keep up.
The trip ended up uneventfully, and we made a perfect landing at our mooring buoy in the yacht club basin. Several weeks were spent modernizing the conveniences and sanding the decks. Air conditioning, heat exchanger, new stereo system, wifi, water heater, BBQ, new shower, TVs, iPad, all the things needed to survive a Toronto summer. I started spending nights on the boat. Other days, I would get down to the yacht club at 10 AM, work through lunch (BBQ!), and sleep in the afternoon in the aftercabin on the double berth, rocking gently and watching the reflection off the water shining on the cabin roof. Home by 6 PM in time for cocktail hour and dinner. Just like an office.
Funny thing, though. My sailing buddy and I didn’t go out that much.  A bigger boat, harder to handle, more comfortable to stay moored, and we were sucked in. We were well on our way to becoming one of those big yachts in the basin that never went out. One of our problems is maneuverability – Passat has a single screw and a full keel, which is the worst combination for turning ability. She weighs 8 tonnes and has no brakes. She can’t go any slower than 3 knots. The only thing she has in her favour mooring wise is a reverse gear that will snap your neck.
We fouled our mooring buoy once, wrapping the line around the screw. That required extensive diving, stress and fuss, and led to me getting a dock instead. The dock was inside the basin, though, nestled among other docks and harder even than the mooring to get into. We made complete fools of ourselves several times the first season trying to land, but fortunately, we didn’t bump any other boats.
So far, one season into owning Passat, the office thing was working out fine. It was the boat part that wasn’t really happening. More on this later