Taylor helms Peccavi on our last October sail

For boat owners, there’s said to be two days that are the happiest of your life: the day you buy your boat and the day you sell your boat.

There’s no doubt that owning a boat is one of life’s great pleasures, and a sail boat even more so. I won’t dwell on the matter of “stinkpots” as sailors call power boats, although I have several very good but misguided friends who own them. Sailboats are defined as a hole in the water into which one keeps pouring money. It’s a fair comment, as the costs of maintenance, repairs from the inevitable equipment failures or minor accidents, docking fees, launch and haul out costs and winter storage do mount up. But I suspect they’re no worse than a summer cottage or a winter ski lodge. For power boat owners, add the massive cost of fuel.

The joy is being able to get out on the water when you want, and go where you like. That’s freedom. Unlike a power boat skipper, who certainly needs to learn docking and undocking skills, a sailor needs to learn a whole lot more about wind (and tide, but not on the Great Lakes, or in the Caribbean), currents and weather. A sailor needs to understand the dynamic of how a boat is powered through the water by the wind, how to tack and gybe, how to sail close-hauled or run before the wind, how to rig and de-rig, essential knots, and much more.

Anchored in the crystal clear waters of Tobago Cays

Sailors can seldom get to their destination in a straight line. On a recent fall cruise to Highland Yacht Club, nestled in a harbour under the spectacular cliffs of the Scarborough Bluffs, the wind was right on our nose. This required an enormous beat miles out into Lake Ontario, tacking at just the right spot and another long beat into harbour. Our powerboat friends just cut the corner and took perhaps an hour to make the trip. We took four hours, but had a wonderful sail. For us sailors it’s the journey, not the destination. The bonus: when I went to fill up my diesel fuel tank after the trip, I only had to put in $15 worth to top off after half the summer cruising.

At Harbourfront in Toronto, where I have been privileged to assist with their adult sailing program for several years, we expect to be able to turn out a decent small boat sailor in four concentrated days of instruction. It’s a tight fit. There’s so much to learn that the students do most of their book study on their own time. The course is mostly practical boat handling. It’s hard work and requires the students to pay attention to the details, but they’re adults who want to learn, not kids who’ve been sent to summer camp, so the pass rate is very high. After passing the basic level in Toronto Harbour, they’re encouraged to take on the Intermediate and Advanced levels during organized February cruises in the Caribbean. In a week of blissful sailing in warm waters during Canada’s miserable winter, the students take on every role on a large keelboat, up to 50 feet on occasion, but more often in the 40 to 45 foot range. Once you can handle one of those suckers, you can handle anything. Many of those I’ve met through these courses have become friends, and for the new sailors it’s an excellent social exercise.

Diane, Amanda, Taylor, Commodore Nigel, Captain Clive in St. Vincent

Some of my best times have been on winter cruises. The first few adventures were with Harbourfront, under the excellent tutelage of Captain Clive, now a good friend. Then I achieved all necessary qualifications to charter on my own. Since then I’ve chartered boats in St. Martin (more than once, it’s a favourite destination), St. Vincent, Placencia, Belize, and more. Amanda, who came along for our Grenadines cruise, has come to love sailing, has just passed her basic level at Harbourfront and will be off cruising out of Granada in February to earn her Intermediate certification. Taylor, who also joined us in the Grenadines, and whom I met during a sailing course, crews on my boat in Toronto, and does a great job at the helm.

Last week, the mid-October weather co-operating spectacularly, Taylor came for a last sail on Peccavi in Toronto Harbour. The wind was gusty, reaching a stiff 19 knots at times, so we had a great time, the boat heeled over and the rail almost in the water. An hour later, the boat at the dock, the main and jib sails were down and packed away for the winter.

Peccavi lifts out of the water

This week, the boat all shipshape and winterized down below, the sails stowed, the boom and mast removed, she was hauled out of the water and put in her cradle for the winter. Joe, who has an identical boat, hauled out at the same time and we helped each other with lines and so on. We also shared a breakfast tot of rum. Haul out may be the saddest day of the year, but the work gang were unfailingly cheerful and expert. Later they’ll come along and cover Peccavi with a plastic wrap to seal her up until we launch again in five months time.

It would be even harder to take if it were not for the promise of a sailing trip in the Caribbean to break up the winter blues. Looking back through my log books and journals, which I keep for all my travels, I’m reminded of brilliant sunrises off Martinique, spectacular anchorages on the craggy coast of St. Vincent, where the first Pirates of the Caribbean was filmed, perfect beaches in St. Martin, snorkelling with clouds of brilliant blue fish off the great reef in Belize, swimming with turtles in Barbados, eating lobster by hurricane lantern in Tobago Cays, challenging seas in the Nevis channel, calm sunsets off Bequia and enough more to fill a library. I wonder where this winter will find us? The anticipation is enough to take the edge off the saddest day of the year.

This article was originally posted on October 24, 2013.

PS: Taylor is also the talented chap who designed the logo for my website.