I am lucky enough to live within an hour of several cities (or large towns) on Lake Ontario, and near "cottage country" which is full of lakes. I'm considering a learn-to-sail program this summer. A quick search reveals a large array of possibilities, all requiring about an hour's drive each way. Some of the distinguishing features among them are:

  • the size of the boat you're learning on. I think I would prefer dinghies (14 foot) to the 20+ and even 40+ foot options at some places. How different is the experience? Can you learn more easily on a big stable boat, then apply that to a dinghy, or vice versa?
  • the size of the lake - Lake Ontario behaves very differently than a small cottage lake, I'm sure, but I don't know precisely how they would differ
  • the likelihood that I would want to join the club or association that offers the lessons, and use their facilities after the lessons are over
  • the schedule. Once a week all summer, 6 consecutive evenings, 3 full days, and so on.

I am not looking for recommendations of specific clubs. I am looking for the relative importance of these factors to the overall experience of taking the lessons. I am reasonably hard to train - if I can't follow what's going on I get angry and stop wanting to participate, but if I feel I'm being patronized or the level is too introductory I tune out. Spending hundreds of dollars on a training course that I bail on partway through, or that is not fun at all, is something I want to avoid. Feeling stupid because I can't follow instructions everybody else can follow, or do something that a mere child can do, or that I should know how to do because I knew it when I was 12 (and could sail a dinghy alone) is the major reason I would resist doing this. The typical summer camp experience where the counselor talks for 5 minutes, then sticks everyone in boats and some of them are great at it and one person is stuck up against the bushes and can't seem to get turned around and is just melting down and has to be rescued but doesn't end up actually being able to work the boat - that's the situation I desparately want to avoid. If a particular size of boat or lake, or pace of training, or qualification of the offering organization, can contribute to the success of this project, I would like to know.

I have some experience as a child with very small boats and a little with a 26 footer. I don't like engines. I believe I might enjoy using a boat that is small enough to actually land somewhere, and there are plenty of lakes in Ontario, whether a small cottage lake that you can see across, or something bigger like Georgian Bay or the Thousand Islands, that we could sail on if we wanted to. We could also try renting a small sailboat (again, small enough that you don't anchor and row ashore in a dinghy, but you pull up on the beach or to a dock) in more far flung places like the South Pacific as part of a larger trip. A picnic on a deserted isle or a tootle around a lagoon would be lovely.

  • take the US power squadron's boating safety course.
    – SkipBerne
    Jan 18, 2016 at 22:24
  • Hi SkipBerne. We're really looking for more detailed answers than that. Also the OP is looking for sailing instruction. The power squadron safety course won't cover that. Jan 18, 2016 at 22:49

3 Answers 3


I was lucky enough to take both dinghy sailing lessons and later cruiser sailing lessons. It's an approach I'd really recommend. Sailing a dinghy will teach you to watch the sails and the wind much more easily than in a cruiser. All the skills you learn in a dinghy will apply to a cruiser (except capsize drill, hopefully). They are also a lot of fun, and much cheaper than cruiser lessons. What you are looking for is Whitesail 2 or Whitesail 3. If you are thinking about sailing in cottage country, as opposed to the Great Lakes, there is a lot you can do with a dinghy-sized boat. A Wayfarer or similar is a great boat for family outings - seats 6 - and you can even use it for longer trips if you throw a tent in it. There are some 17-19 foot boats with small cabins that can be easily sailed on the Whitesail courses.

If you do start on dinghies a smaller lake is better than a larger (by larger I mean Lake Ontario or Lake Simcoe). The weather won't be as severe, and there is less traffic. Again, the kind of lakes you get in cottage country are ideal for dinghies.

If you are looking to sail a 30-footer then you really need to take a specific Cruising course. There will be some benefits to taking the dinghy courses first. However you shouldn't skip the Basic Level Cruising just because you have dinghy sailing experience. There is some stuff you need to know about cruising that dinghies won't prepare you for. However in cottage country a 30-footer isn't really much more fun than a 17-footer.

If you are looking for recommendations in Southern Ontario, get in touch and I can let you have some.


From the sounds of it, to develop all the skills you are interested in, you are not going to learn them all with a single class. Additionally, it will likely take several years to hone your skills to a point that you can depend on them.

For learning how to harness the wind, it is better to learn on a smaller boat. Something like a sunfish, laser, or a Hobie 16 catamaran is ideal. Because of the light weight of the boat, it will give better, more immediate feedback to how well you are operating your sails. A Sunfish, with only you in it, will only weigh maybe 300 pounds or so, and is capable of stopping almost immediately if you dump your sails or improperly turn upwind. A much larger boat, weighing 2000 pounds or more, if you have decent speed can easily coast through a shoddily performed turn, and while it can be a little more forgiving in easy weather, it comes at a result of making it harder to develop core sailing technical skills.

Furthermore, smaller boats don't have as much inertia, so you can be a bit more aggressive and try more difficult maneuvers, and capsizing them is virtually a non-issue. The smaller boats are also less expensive. You'll be much more willing to push the boundaries of your skill with an $1,500 boat than an $80,000 yacht.

As far as lake size goes, it isn't terribly important, anything about a square mile in size or more is sufficiently large for a small boat like a sunfish. If you are honing your technical skills, you're going to be tacking or gybing virtually non-stop. Obviously, if you are learning on a huge 40 foot yacht, you're going to need a bigger lake. In my opinion, smaller is better than bigger for learning base technical skills.

When you start moving on to bigger boats, you don't so much learn more 'sailing' skills, you learn mariner skills. The new stuff you learn isn't about capturing wind, but of navigation, rights of way, maintaining equipment on your boat, handling sleeping while at sea, and more. The sails get bigger, but their basics of operation are mostly the same.

I'm going to end there, because I don't want to write a novel on going from complete novice to master of the seas. Once you are capable and confident to sail around a small lake from any point to any other point, in a wide range of weather, you'll know what you'll need to learn and work on to make a trip to Ontario or elsewhere.


If you have the option, small boats give you the best feel for how sails work and how changes in trim affect the boat and your course, so at least start on a small boat.

Also, taking a few full days will help far more than a bunch of evenings. You develop a feel for sailing over time so for your initial training, intensive is a good thing.

Growing up in a very windy part of the Atlantic Ocean I would suggest a larger lake well give you more experience of decent wind and waves, although I'm guessing you won't get tides. This is good experience and good fun.

Distance to your house is important but not essential. You may get hooked and knowing where you can get to quickly for an evening's sailing is useful.

All the best with it - I have been sailing for 35 years now, taught at an RYA sailing school 23 years ago, and am hoping to get all the kids into it over the next year now the youngest is a strong swimmer.

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