A sailor is an artist whose medium is the wind

You might just be a little curious about sailing. Maybe you grew up landlocked in a country (like me) and the prevailing culture expected, or perhaps demanded, something different from you. But, in the back of your mind, you sought an escape from the confines of your territory. Perhaps you would buy magazines of sailboats and simply dream — and that was the extent of it; or maybe you were so inclined as to draw sailboats on the back of exam papers — and a passion was born. But, what if you were curious enough to take your yearnings to another level. Just maybe, you devoured anything and everything ‘sailboat’ that came your way; and perhaps you even self-taught yourself all the sailing phraseology, before going forward and purchasing your very own boat, when the time was right. Maybe, you felt that “…a plunge is to be made into the water, [and] it’s of no use lingering on the bank.” So you dared to fulfill a dream. If this at all sounds like you, keep reading.


Whatever your desire for the open sea, there is a lot more to buying and owning a sailboat than meets the eye. I’m here to help you take the plunge into the water — it’s not all that scary, to be honest. In fact, I’m about to make it a lot easier for you. So grab the tiller and enjoy — I did some of the grunt work already and I’m laying out the instructions below.

Firstly, you need a pleasure craft licence (a step that can be easily overlooked). I quickly found out that I could get one from a simple online exam. I wasted no time when the opportunity arose; I went through all the modules on the website for roughly 10 hours before moving directly ahead with the exam. My licence came in the mail within a week — and it’s now good for life.

Next, consider investing in a book on sailing. You might think you can go without (with all the modules you got through for your online licence), but honestly, don’t stop your learning once you've acquired it. The modules don’t dig deep enough, and you should be relatively fluent in the language of sailing before you’re serious enough to buy a boat. That being said, there are a few good books to choose from online, but, I was sold on the book called: Sailing for Dummies. Just so you know, it doesn’t have to be an encyclopedia.

Here are a few additional things to keep in mind.

There is the initial upfront cost for the boat itself, but there is also an annual cost. These annual costs can range quite a bit depending on the type of boat, the year it was built, and, of course, wear and tear (stuff that breaks and needs replacing also needs to be factored in). Overall, you can expect to shell out over a few thousand dollars a year. Your sailboat service manual (be sure you have it; and I wouldn’t buy a boat without one) no doubt contains a list of the parts available for purchase; and how to go about doing so, should you need to place an order.

However, before you buy a sailboat, there are a few things that you should never compromise on, for safety reasons; and one of these exceptions is the structural integrity of the hull. Safety should be taken very seriously and, therefore, the soundness of the hull is probably the most important factor. A working radio, a lifebuoy ring, flares and plenty of rope, are a few additional safety essentials, among others. Preference for the size of the boat you choose to buy, should largely depend on where you wish to sail; with recommendations for vessels of up to 30ft if you’re planning on traversing the ocean.

Also, keep in mind that the boat trailer needs to be stored. To have it stored at the marina indefinitely is a factor in the annual expense. Not to mention, that you may need a new set of trailer tires if the sailboat is being hauled a long distance, or stored improperly; and possible electrical work may need to be done, so that it is compatible with your vehicle. You’ll need to pull the boat in and out of the water periodically, and, therefore, a vehicle with a towing capacity well above the recommendation (to compensate for the water collected in the hull) would be wise. Moreover, registration and boat insurance are a requirement for most vessels, which you can typically combine, together with your auto insurance and registration. Not only that, but if you live in a cold climate you’ll likely need to winterize the boat. This entails covering it with tarps to protect it; and possibly removing and storing the outboard engine. It goes without saying that these are all considerations that should be addressed beforehand.

When I bought my boat (a 22ft Catalina), I had the previous owner rig it as a condition of sale. For, I had no idea how to put it all together, myself. There are many intricate parts beyond just the mast and sails, but I learned a heck of a lot on the day the rigging went up, just by watching. The previous owner was an old man who'd owned the boat for a number of years prior, and who'd since retired. He didn’t pass down the boat in the best shape, because he no longer had the energy for it; but I fixed it up like new over the next few years.


The sailboat was moored out on the water the day following rigging with the old man. It was attached to a buoy about a hundred feet from the dock at the edge of the water. As I drove out to the reservoir to learn to sail it on my own, I could see it bobbing in the water among the other vessels — and my eyes lit up. For me, it was a symbol. It was a goal that was reached — a secret goal, which I told nobody about until after the fact. You can be sure it didn't go down too well with the parents! But once it was a done deal, I got my friends out on that boat and we all spent a summer learning to sail together. Friends that would otherwise never have got the chance. I look back now and I don’t regret my decision to take the plunge one bit. So here I write to the misfits and rebels that are bold enough to change the world: you might sink or swim, but at least you dared to dream. I kept the sailboat a few more years before I passed it off to someone, in much better shape than when I first bought it, and for less than half the price... I put a lot of work into the sailboat and I got nothing but great memories in return.