How did you learn to sail? How can I learn to sail? Variations of this question are one I’m most frequently asked. There are many answers and many paths. I’ll share how I got started. I almost typed “how I did it”, but I’m not done learning. Drum roll…

Buy a boat. The first actual step I took toward learning to sail was buying a boat. I didn’t know anyone who sailed. I didn’t know anyone who lived on a boat. I didn’t know anyone who owned a sailboat. With that in mind, I did what I’ve been known to do with life-altering decisions. Act first, figure it out later.

It’s worth noting that I’d done quite a bit of mental preparation in advance. I’d decided I wanted to live on a boat when I was about four. As a kid in Seattle, I couldn’t help but be drawn into the allure. So I was hooked before I knew any different. After spending some years growing up away from Seattle, I returned for college. It didn’t take me long to make my way down to Elliot Bay Marina from my studio apartment in Magnolia. There’s something either humbling or insane about staying up late at night trying to figure out how to come up with $70,000+ for a sailboat when your apartment is furnished with an air mattress and a guitar amp and your diet consists primarily of rice. Eventually, I managed to temporarily quash the desire for life above liquid.

In February of 2008, I was totally unattached. When I say totally I mean it. Homeless, jobless, relationship-less, car-less. I’ve told snippets of that here before, so I’ll skip the details for the moment. Naturally, finding myself in a unique position, I secretly started looking at boats online. To further commit myself, I bought some non-inexpensive books on the nuts and bolts of sailing skills and the nuts and bolts of boats and boat systems. I had a few bucks in the bank, but not nearly enough to buy the kind of boat any reasonable person would buy with the intent to sail it for more than an afternoon. It didn’t matter, I did what the clinically insane are prone to do… convince myself that I could sail a 25′ boat, built in 1967, around the world. That’s a bit strong actually. I merely convinced myself that I could at least sail around the coasts of the Americas. Yes, all of them. When I went to look at the boat, the guy selling it did me the disservice of taking me out for about a 30 minute sail. My suspicions were confirmed and it was a struggle to keep a poker face through the urge to grin in order to avoid paying more for the boat than what he was asking. In any case, show’s over. I had to do it. The reaction of the cute bank teller when I told her the cashier’s check was for a sailboat prevented buyer’s remorse from even beginning to form.

The first week I spent on the boat was spent trying to answer the “how to learn to sail” question for myself. I read my sailing books. I stressed out. I made up excuses about the boat being incapacitated whenever anyone asked why I wasn’t going sailing on beautiful days. I don’t remember the exact circumstances, but the answer did finally come to me.

The yacht club. As it turned out, the tiny town in which the boat was moored had a yacht club. The important part was that they offer a free sailing class every spring. That proved to be the turning point.

Have you ever been invited to, or actually gone to, those free trips to Vegas things? You know, the ones where they offer you a free trip with the one stipulation that you have to sit through their sales pitch. Well, the yacht club was much more subtle in their cult-like psychological manipulation, but the free sailing classes are the free trip to Vegas. Their whole point is to get you to plunk down cash for membership afterward. Don’t get me wrong, I didn’t mind. It was pretty much a foregone conclusion.

Perhaps some of you reading this are members of the San Diego Yacht Club or some other extravagant facility with elaborate requirements for membership. Before I thank you for setting a stereotype that people love to fling at me when I tell them I’m a member of a yacht club, I’ll give you permission to exclude this yacht club from your definition of yacht club if you must. I’ve never seen anyone here in one of those ridiculous white hats. They never made sense to me anyway. I always get the image of Mr. Howell and The Skipper mixed up into one person. Oh well, I’ve always seen myself more as The Professor anyway. So… If the millionaire yacht owning set don’t conduct sailing classes as thinly veiled indoctrination of wanna be sailors to enrich the club’s fortunes, I’m okay with that. Oh, and thank you for being the source of the stereotype of country club without the golf.

If there’s a yacht club in your vicinity and you want to learn to sail, contact them to see what’s available. Sailors, while competitive, are one of the most helpful groups of people I’ve come across. Even if the club itself is restrictive, there will be people there excited about anyone who’s interested in sailing. If you already have a boat, it’s even easier to get them to warm up.

If there’s no yacht club, read the books. You can learn a lot from the books. You can learn enough from sailing books to start sailing without instruction. It will probably be a little tricky at first, but it’s possible.

After reading the books and taking the classes through the club (they were almost exclusively theoretical/lecture type classes), my next step was… terror.

If I hadn’t spent a few decades convincing myself that I loved to sail before I got out in a 24′ boat in 12′ swells, I’d have sold the boat in a hurry. I’d been on the water a few times in mild conditions and life was grand. Apparently, the ocean isn’t like it is in the happy-fun-time sailing movies. Sailing isn’t like it is in the happy-fun-time movies. I started sailing on the Pacific Coast of Oregon. The stretch of coast that’s referred to as “the graveyard of the Pacific”. Maybe you’re aware of this, but there is no such thing as a happy-fun-time graveyard movie. There are people reading this who will sigh and tell you stories about how they’ve braved seas the size of Everest without batting an eye. Congratulations to them or their storytelling prowess. I’m not writing this for them. I’m writing this for new recruits.

Another thing that was less than fun to realize is that sailing rarely involves anything horizontal. The boat is typically heeled over significantly to one side or the other. I know a few things about physics so this shouldn’t have been any surprise, but I guess it never registered.

There’s only one reason I’m talking about the negatives at all. Like almost everything, our enjoyment of something largely depends on our expectations matching up with reality. If you think sailing is all cocktails and bikinis, you might not like it without an adjustment in your expectations. For me, sailing is like learning to drink wine and learning to drink beer. If I hadn’t decided that I wanted to acquire a taste for them prior to tasting them, I wouldn’t have lasted long.

Who knows. Maybe you live in Miami and the water is warm and flat as far as the eye can see. I wish I’d been able to get the basic skills down in a calmer area. There are great days here, they’re just harder to catch than in some places.

Now that I’ve said all that… There seems to be a general idea that sailing is super difficult to learn. I disagree. I was in love with trimming sails the first time I tried it. There are nuances of course, but learning the basics isn’t some sort of secret knowledge. I recently stumbled upon a couple who’s circumnavigating. Before they bought their boat and sailed away, they had something like TWO DAYS of on the water sailing. They left from Florida and are now a couple months northwest of New Zealand. It can be done. Do it.

Where am I in my quest for master seamanship? Progressing. I’m to the point that if I had a boat I felt I could rely upon, I’d feel good about sailing anywhere within reason. I’d be obsessive about watching the weather, but I’d feel good about it. I haven’t reached any sort of mastery and really still consider myself a novice. I’ve learned enough to be able to learn more.

If I haven’t answered the original question for you by now, let me sum it up. If you can’t get out on the water with someone who knows what they’re doing, read as much as you can. If you don’t have access to the books, find someone and get out on the water. If you’ve already decided that you want to sail, just buy a boat. You’ll figure it out. Seriously.