I really want a sailboat.

I know that’s kind of apropos of nothing, but there it is. I want a sailboat and I want to sail it.

A few years back I was in a really bad time in my life — I was living alone in London, I was recently single, I’d burned-out rather thoroughly as an activist and I was working a shitty job at a shitty call centre, barely making ends meet. I was, to put it kindly, in a rather nasty rut and I spent most of my days in a low-grade haze of miserable depression. It was one of the worst times of my life… but a couple of positives did come out of those grey days: The SCA, and my first experience with sailing.

A friend of mine had a little water-ballasted Hunter 23.5 fractional sloop down at Port Stanley and on a few occasions he and I went sailing on Lake Erie, both day and overnight trips, while he taught me the rudiments of sailing. In fact, after two sailing seasons and half-a-dozen trips, he’d gotten confident enough in my abilities that he even lent me his boat for a solo sailing trip. For three glorious days one July, I single-handed from Port Stanley to Rondeau Provincial Park and back again; there was no self-steering, so I spent every nautical mile with one hand on the tiller; at anchor off Erieau I spent the whole time banging my head on the cabin top; I lived on granola bars, stale bagels, cold tinned stew and warm beer… and I got horribly sunburned and bug-bitten in the process.

It was awesome.

That led, inevitably, to the notion that I could get my own boat, maybe a 30-footer, and I could sail her single-handed around the world. I wouldn’t be leaving anything important; there was nothing to hold me back at that point in my life… except, of course, for the whole money issue, which pretty much shot that plan through the head. Getting even the most beaten-up 25-footer would cost a couple of thousand dollars, and fixing her up would cost more, and then I’d be looking at having to pay for provisions, repairs, etc. I sat down and did a budget and came to the conclusion that, best-case, I’d need about $15,000 just to get started and another $1000 a month to keep going… and that didn’t count the mountainous student loans for my unfinished degree.

And what with one thing and another I quit my awful job later that summer, tried to get into Western, got into some financial trouble due to being screwed over by my roommate at the time, moved back to Peterborough and eventually finished my B.A. in Classical Literature, then focussed on the SCA and finding a job, and then I met The Wife™ and we got settled down and now we have a house and a couple of dogs and I’ve got a good job and holy shit do I ever want to go sailing again because I just realized those three glorious July days on Lake Erie were in 2005.

Dropping everything to go sailing around the world is clearly not an option for me anymore. Ironically, my finances — the only thing which stopped me a decade ago — are now the least of my worries; It’d be a struggle, but I could possibly make the money work in a couple-three years. But where in 2005 I had nothing at all holding me to shore, now I have a whole life here… and it’s a very good one. The Wife™ certainly hasn’t expressed any interest in abandoning her career and home in order to indulge my Joshua Slocum fantasy, and I don’t blame her: I was once told that you can make a reasonably-accurate sailing simulator by standing fully dressed in a cold shower while tearing up the contents of your wallet.

So I’ve adjusted my thinking. A friend of mine has a Sirius 22 which he takes sailing occasionally, and for a night or two it’s perfectly adequate for him and his family… and a damned sight cheaper than a big cruising boat. With that example in mind I’ve been considering the possibility of saving up for something similar, a trailerable daysailer like my friend’s Sirius 22, or that old Hunter 23.5, or maybe even something as big as a Northern 25, and I’ve done some research on local marinas and yacht clubs with an eye towards mooring and haulout fees, and so on. And you know what? I think it might be do-able.

Of course, it’s not as simple as just “getting a boat and going.” For one thing, it’s been damn near a decade since I’ve set foot in a sailboat and I don’t have any of the necessary licenses or permits to legally operate a small craft, so I’d be looking at taking a course in sailing and getting the paperwork sorted out… but that’s a do-able option as well. Certainly there are courses available within an easy drive and most of them have a hands-on sailing aspect to the lesson plan, which would also get me out on the water again in the short term… and if I can convince The Wife™ to join me it might increase her enthusiasm for the project, as well as her confidence in her potential skipper.

As a quick aside (and for the record) I just want to say that it’s not that The Wife™ lacks confidence in me per se… but she did once watch me accidentally clog the vacuum cleaner with a sock that I happened to be wearing at the time, so I’m willing to concede that she might hold some concerns about whether I can handle the complexities of a sailing rig. Getting properly trained and licensed strikes me as an excellent way to allay any potential concerns as well as just being good common sense from a safety standpoint.

But I am putting some serious thought into signing up for sailing courses next spring and summer. Once I’ve got some experience and the proper paperwork, I might be able to beg, borrow or rent a sailboat for a weekend or two just to get my feet wet again (so to speak) in a year or two, and then if we decide it’s something we enjoy we can make some long-term decisions from there.

Wandering the world in 30-35 feet of sailboat is not, alas, an option. But weekend sailing on the Great Lakes? That’s achievable, and it’s easily achievable within the next five years. Instead of the fantasy of setting off for a circumnavigation of indefinite length, I’m now daydreaming of a sailing tour of the Thousand Islands on a long weekend, or taking a vacation cruising Georgian Bay and the North Channel, or daysailing trips from Port Hope or Cobourg or Brighton and for some reason I find those dreams far more exciting than my old live-aboard fantasies… maybe because they are attainable.