Tacking

[s/v Jedi]

When racing, it all depends on your current position in the field. When I was in 2nd-5th place of a 60-boat field, I would follow the ones in front of me until we enter the last phase. When I am further behind, I would go where the others in front of me are not going, even if I would need to start with a bad tack. The less wind and the more land features, the higher the chance to significantly improve your position that way... but also high chance to loose even worse (which didn't matter when outside the prizes already). In the hundreds of times I tried this, it worked really well 3-4 times. But those were worth it ;-)

But I am not sure if this is about racing... VMG is perfect for cruising, combined with favoring the side with less wave action or less heavy gusts.

cheers,
Nick.

[donradcliffe]

The answer is that it depends on a whole lot of things--that's what makes sailing interesting--but the short answer is the tack with the best GPS VMC (velocity made good to the destination), unless you are pretty sure that conditions are going to change before you arrive. If you want to get really sophisticated, you can use routing programs like Deckman or Expedition along with your boat's polar speed diagram and grib wind files, but over 90% of the time they will give you the short answer.