I wish I had a dollar for every time I’ve heard that over my career. It is by far the concern most often expressed by people looking for help. So let’s take a look at tips, tricks, and what it takes to get your boat sailing its best upwind.

We’ll start by skipping the most obvious, blown out sails. While these can certainly have a large effect on your performance, if they are the problem there is only one solution… replacing them. So the most basic answer as far as we are concerned for this article, and really the only answer, is understanding what things on a boat you can do to improve performance, and then implementing them in a controlled manner where you can verify the results.

I start by asking the person “What do you think are the two most important things you can do to improve your pointing”, and usually I get an answer that is mostly a blank stare and something mumbled about never having really thought about it. After teaching and coaching for over 30 years I can tell you that by far the answers for most people are straight forward; trimming the main leech tighter and doing a much better job concentrating on their driving! And concentration is the most important. The biggest percentage of people that have trouble point simply don’t point their boat high enough, often enough. As I heard a competitor say once a long time ago, “If you aren’t pointing high enough, just push the tiller away from you”, and for far too many people that is answer.

Except in very light air or extra bumpy conditions you start by making sure the mainsail is trimmed so that the boom is absolutely up on the centerline of the boat when the mainsheet is trimmed hard enough so that the telltale on the leech at the top batten is stalled out some of the time in any condition where you are not overpowered. In light air, under 6 knots, it will be stalled most of the time. Once you get into the 7-10 range it will be stalled maybe half the time and in over 10 it will be stalled only occasionally, but you need to have the leech sheeted as tight as you can without being over powered. Once you get into the real overpowered range, over 12 knots, you still need to keep the leech very tight for pointing but you may drop the traveler down so the boom is just enough to leeward to reduce extreme weather helm that comes from letting the boat heel too much. The leech on the main is the biggest factor you can “trim” to improve your pointing.

Once you have the sails trimmed in the rest is all about driving the boat. Here it really helps you have a good set of target boat speeds and an accurate speedometer. For sailing your best upwind it should be a true speedometer and not a GPS, the time lag in a GPS seems to be just enough that it doesn’t quite line up with the actual boat speed fluctuations as you feather and steer the waves. Here it is all about concentration, keeping your boat sailing as high as it can and steering up in every puff and in every chance you get between waves. On a two mile beat really good helmsmen will be looking for all those little places they can point higher for just a second or two, and then quickly falling back off before the boat speed gets too low. If he gains 5 or 6 feet to weather every time he does that, and does that every 200 feet, the net gain straight to weather will be in the 350 to 400’ range!

To win races upwind, sheet your main in a little tighter and then drive your boat better than your competition. To drive your boat better means you have to have better focus and better concentration.