I've never been much of a gambler. In fact, I've been to a casino only once in my life. I must admit I had fun that night, even though I lost quite a few dollars. My main problem was ignoring probability. At the blackjack table, for example, I'd typically ask for another card when I had 16 (and sometimes even 17). That was obviously not a winning strategy.
Just like the casino, a sailboat race presents many opportunities to gamble. Almost every sailor rolls the dice at least once in a while and heads off on some sort of "flyer." The best sailors, however, minimize the chances they take. They calculate the probabilities of every move, and stick to the ones where the odds are stacked in their favor.
It's almost impossible sail a race on pure strategy (as if there were no other boats to encounter during the race), and it would be foolish to sail a completely tactical race, without some sort of strategic game plan. Strategy and tactics go hand-in-hand. Before we get into boat-on-boat maneuvers, let's look at some of strategic principles that provide a transition into tactics, and that can help stack the tactical deck in your favor. We've discussed some of these ideas already; others are new.
Start where you'll have clear air and speed.
When I was growing up, my sailing instructors told me to start at the "favored end." That was a great concept, except for one little thing: everyone else had the same idea. For every perfect start I've gotten at the committee boat or pin, there have been at least three or four starts where I fouled out, found myself stopped dead at the gun, or ended up in the third row.
I'm usually a pretty good starter, but heading for one of the ends is clearly a low-percentage move. I recommend starting a quarter or a third of the way down the line. Here you have a much better chance to get clear air and come off the line with speed, and that alone will put you ahead of 90 percent of the fleet.
Sail the tack or jibe that takes you closer to the next mark.
Again, this is a fundamental rule of thumb, and it works almost every time. When you're sailing upwind or downwind, and you can't fetch the mark, stay on the tack where your bow is pointed closer to the mark. By sailing the longer tack first, you will benefit from almost every potential windshift. The farther you are from the mark and the closer you are to a layline, the more important this is.
Sail toward the mark whenever possible.
It's a fact of geometry that the shortest distance between two points is a straight line. Therefore, when you're fetching the next mark, don't waste time and distance by sailing high or low. Aim at the mark so you maximize your velocity made good toward it. The farther you are from the mark, the more important this is.
This principle particularly applies is when you overstand the mark from far away. You'll get to the mark fastest by sailing straight at it, no matter what the wind does. Of course, there could be tactical and strategic reasons to sail high or low. As you get closer to the mark, for example, you may want to hold high so you won't have to tack twice in case of a header or bad air.
Stay between your competition and the next mark.
In other words, cover. This is the surest way to stay ahead. The farther you stray from your competitors astern, the more they will gain on a windshift in their favor. If you stay directly upwind of the other boats (or downwind of them on a run), their gains will be minimal, no matter which way the wind shifts.
Unfortunately, covering is not always as easy as it sounds. If you apply a tack-for-tack cover when the wind is shifting, you may actually lose. That's because if the boat behind hits the shifts perfectly, you will be slightly out of phase. So the safest thing is to keep sailing your own race and cover loosely.
Set up your rig and sails so your boat is easy to steer.
When you're trying to get around the buoys as fast as possible, boatspeed is key. Your goal should be to keep your boat's performance as close to maximum as possible.
There are a number of things that make it difficult to keep your boat going fast all the time, including waves, changes in the wind, sailtrim mistakes, and helmsperson inexperience. The best way to compensate for these factors is by giving your boat a wide "groove." Set your sails so they are round in front, and be sure not to overtrim. You may give away a little pointing ability, but the boat will maintain much better speed for a higher percentage of the time.
Leave plenty of time for boathandling maneuvers.
One of the quickest ways to ruin any race is with a boathandling disaster. Think about the last windy race you sailed. How many boats went around the leeward mark with their spinnakers in the air, in the water, or in shreds?
The best way to prevent disasters is to practice, practice, practice. Once you're racing, the only insurance you have is time. Most leeward mark disasters, for example, can be prevented if you leave yourself a little more time before the mark.
I know there are a lot of purists out there who hate to douse a spinnaker before the bow gets to the mark. But believe me, the slight amount you gain by leaving your spinnaker up for an extra boatlength or two is not worth increasing the risk of having a screw-up. Especially on windy days, execute early to get the highest returns.
Watch the good guys.
There are not many shortcuts to successful racing performance, but this one usually works. If you're not one of the top sailors in your fleet, or if you're racing in a new area, keep an eye on the boats that do well consistently. How do they trim their sails? Which side of the course are they playing? Keying off a top sailor who knows the local area will usually increase your chances of success. As the saying goes, "When in Rome . . ."
Even better than watching the good guys is sailing with the good guys. I suggest looking for every possible chance to get into a racing environment with sailors who are more skilled than you. My own abilities have improved the most while crewing for people like Dave Perry, Buddy Melges, and Dave Curtis.
Go for many little gains rather than one big gain.
Taking a flyer on the first beat is a little like spending your paycheck on lottery tickets. Everyone wants to get rich quick or move into first place instantly, but the chances of this are extremely small.
In most races, it's much easier to gain a little here and there than to gain a lot all at once. So be patient. Look for high-probability ways to pick up a few boatlengths at a time, and you'll maximize your chances of making a larger gain over the course of the race. The farther you are from the finish, the fewer chances you should take.
Remember, you don't have to gamble to win races. The best sailors are those who choose tactical and strategic moves that have a high probability of success.