So, you’ve decided it’s time to stop dreaming about the wind blowing through your hair as you cut through the gentle chop of the inner harbour. The CN Tower pierces into the sky above, the water sparkles off of the bow wave, you can feel the freedom of opportunity — like the world due south is open for the taking until that tower is but a toothpick in the distance. Yes. It’s all yours for the taking. You’re going to buy a sailboat in Toronto.

Here are some questions you should consider before you hoist sail.

1. What is Your Budget?

Unless you’re ripping down Bay Street, isn’t this is first question asked in the pursuit of anything? Not only does cost affect the type of boat you’re going to get, it’s going to factor into where you’re going to keep it and, ultimately, the things you’re going to do with it.

Sailing: the most expensive way to get somewhere for free.

Prior to buying our first boat, we were under the impression that a sailor’s life is an expensive one. And it can be. But it is also something you can budget for if you’re willing to put in some work and learn to be more self-sufficient. There truly is a boat for every budget. If you do your research, shop around, get advice, and take on challenges yourself, your sailing costs start to fall drastically.

2.Where Are You Going to Keep It?

Factors that affect this are multi-faceted. There are a total of 17 prospective sailing clubs in the Toronto core alone, and each one comes with different fees, facilities, and distance from home. Not only that, but each one comes with its own ambiance, catering to different types of sailors. 

It can be overwhelming if you’re buying your first boat in Toronto and you’re not sure where to begin. Do you prefer the ease of a dock finger, or does the seclusion of a swing mooring sound more your style? Perhaps the distance from your boat to the club bar is an important factor. Or maybe you’re not interested in being part of a club at all, and the full-service nature of a marina aligns better with your boating needs. Maybe you’re not quite sold on owning your own boat at all (that’s okay too!). 

Toronto offers options for all of the above. Do your research, take in some open houses, and choose what works best for you and the type of sailing you want to do. 

Speaking of which…

3. What Kind of Sailing Do You Want to Do?

Are you looking to get involved in a competitive off-shore racing league? Perhaps you see yourself spending your afternoons tacking around the inner harbour single-handedly. Maybe you fancy yourself more of a cocktail sailor, enjoying the social scene after a breezy afternoon under the sun. If you like the idea of intensive activity close to the water, perhaps dinghy sailing is for you. There are a number of small keelboat clubs along the waterfront, and you don’t even have to have your own boat to join.

Different boats for different folks. That’s how the saying goes, right? Once again, research is key.

4. How Handy Are You?

Does your fix-it knowledge max out at hanging a picture on the wall? If so, some real speed bumps might lie ahead if your future boat is in need of some serious maintenance.

A fact of the matter is, all boats need TLC now or then or constantly. It’s a never-ending labour of love, and something is going to have to be fixed eventually. What matters the most when you’re considering buying a boat is the level of work that is required to get it in the water and start sailing today. Some fix-it projects can be undertaken over a season or two, such as refinishing the teak or replacing an old sail. Some projects are imperative to your boat’s ability to sail, or even float.

Our tip: for your first boat, try not to dive too deeply down the fix-er-upper rabbit hole. You don’t want to become disenfranchised if you find yourself spending more time working and less time sailing. Buy a boat that is ready to go.

5. What Kind of Experience Do You Have?

If all you have ever sailed are single-handed dinghies, it’s safe to say that a learning curve might apply when it comes to docking a 44′ catamaran. Or, if your current knowledge of how to operate a sailboat treads largely in the theoretical realm (re: slim to dreaming), it may take some time to come to terms with the function of the many lines around the boat.

This isn’t to say that you can’t start from scratch and dive right in, but some boats are more patient teachers than others, some rigging is more simply laid out, and some arrangements simply easier to handle.

Note: before buying your first sailboat in Toronto, ensure you have your Pleasure Craft Operator’s Card and Toronto Harbour License. 

6. How Many People Will Be Joining You Aboard?

There is something to be said for listening to the gentle lap of waves against the hull as you watch the sun set behind the golden cityscape and take a moment to reflect on where you’ve been and where you’re headed.

If, in your vision of this scene, you’re sitting with a small contingent of your closest friends, this could influence the type of sailboat you’ll need. Playing the role of hostess-with-the-mostest may be a bit trickier to do if, say, your boat is a 15′ Albacore.

Some vessels could easily be mistaken for floating clown cars, with an abundance of berths, and storage galore to house you, your spouse, three kids, and the pooch. Remember: just because you can fit inside, doesn’t mean you’ll do so comfortably.

7. What Are Your Long-Term Sailing Goals?

Hopefully the answer to this question is Yes, Duh! And that’s why you’re here, gleaning as much information as you can before you take the plunge and buy your first sailboat in Toronto. What these goals are, however, may vary.

Maybe you’re just looking for a weekend escape. A cottage getaway without having to leave the city. An escape from the bumper-to-bumper traffic. An excuse to spend your time in the fresh air.

Maybe your primary goal is to take on an active sport while mastering some new skills. When it comes to sailing, there is no shortage of things to learn.

Maybe your goals lie in travel. Around the Toronto Harbour, around Lake Ontario, around the Seven Seas. The sunset awaits. In accomplishing the latter, buying your first sailboat in Toronto is a great place to start.

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