Many people think it’s best to simply split from the group if they’re behind, going for the “Hail Mary” pass. But if splitting means going the wrong way, it only puts you farther behind.

The better move is to play the wind correctly and patiently wait for others ahead of you to make mistakes. Mentally, it is tough to resist splitting, but you’ll be better off focusing on doing the right thing.

Earlier, I said it’s OK to take more risk, but what I’m talking about is calculated risk, meaning you take a little more leverage to the side you think is correct.

Let’s say the right side of the racecourse was best on the first beat because there was more wind. On the final beat, when you are behind, instead of sailing a conservative 80 percent of the way to the right side, take more risk and sail 95 percent to the layline. You don’t sail 100 percent of the way to the layline when behind because those ahead may tack on you and you want to leave some space for a clearing tack.

As you approach the finish line, you need to determine which end is favored, and do your best to finish at that end. On upwind finishes, the downwind end of the finish line is closer and favored. I figure out the favored end by pretending it’s a starting line and comparing the angles of other boats to it to determine the favored end as if it were a start. Then I finish at the opposite, downwind, end. I do this because it’s easy to figure out the favored end of a starting line by watching others sail across it, or by comparing my own angle to it. When the committee boat end is favored, boats sailing across the line on starboard look really “bow up,” sailing almost perpendicular to the line.

When the line is square, boats sail across at a 45-degree angle on both tacks, and when the pin is favored, boats are sailing more parallel to the line pointing toward the pin. Port-tack boats crossing the line near the pin will look “bow up” with a pin-favored line, and they will look “bow down” if the committee boat is favored.

Another method is to look at the flags on the finish boat and use them to determine the downwind side of the finish line. The flags tend to point toward the favored end. The only downside with flags, however, is that they are hard to see from a distance, and turbulence from the race committee boat can affect their angle. I trust sailing angles most, but with either technique, you should pick the closer end and do your best to finish there.

If you happen to be bow to bow with a few boats at the finish, you can “shoot” the line to gain a few extra feet. Depending on how far your boat will glide in the given conditions, you can steer the boat directly toward the line, gliding across with speed and sailing less distance. Having called many tight finishes, the boats that time their glide will often save critical points.

In conclusion, stick to the basics of sailing upwind on your second beat while factoring in those boats around you. If you are happy, cover. If not, take a little more risk toward the favored side. When approaching the finish, figure out the favored end, and finish there.

Read Steve Hunt's final installment on post-race routines.