It's not just a question of having the wind directly on the nose or up the chuff. It's usually at an angle to the direction of travel: the ideal situation for aerodynamic reasons is to have the wind just abaft the beam (i.e. coming from about 100 degrees from where you want to go, or slightly behind you). This gives the fastest sailing in modern yachts but I suspect that the optimum angle for a square rigger is further aft.

So the best route is one which puts the wind on or abaft the beam for as long as possible - and gives minimum head winds - and avoids the horse latitudes and doldrums, and storms of course...and takes maximum advantage of the favourable ocean currents and avoids the adverse ones etc. etc.   So it's not a simple problem!   How the sailing ship masters did it successfully time after time 150 years ago with nothing but a chart, a compass, a log line and a sextant never fails to amaze me.

Whether they were going to Botany Bay, Round the Horn and back Again, Ten Thousand Miles Away it was an amazing achievement.

Steve