This depends entirely on factors you haven't stated, notably wind and sea conditions, crew experience, and what the other captains are doing. Any tack reduces a boat's SOG, so the more tacks one takes, the more energy is wasted. In rougher seas or light airs, this is more problematical. However, if you have a lead, tacking to cover your opponent may well pay off. This of course means that you tack as quickly or moreso than your opposition. The shortest distance is a staright line, so long tacks that vary from the COG to the mark are problematical. However, this is offset by the speed and momentum one accumulates on long tacks. If your crew is inexperienced or not used to the boat, seas are high, or the wind is exceptionally light, long tacks are the way to go. If you're tactically covering an opponent, especially with brisk winds, flat seas and an experienced crew, tacking to cover works nicely indeed. If you find that the course to the windward mark is nearly accessable on one tack, then that's a grand way to go. If the mark is directly to windward, then you're stuck making the best of two non-ideal choices.
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