You, on the other hand, need to be watching and ready, and as soon as you get near to the waypoint you will be told of the next waypoint - click on this on the minimap as soon as it appears and you can 'cut the corner' and hence save a significant amount of time.
The key with the race strategy is that you can't beat the other ships on speed on the straights, but you can pass them in the corners (at the waypoints)! The other ships will sail to each harbour waypoint and stop for a few moments before setting off again.
Get this, put it in your flagship (make sure there's no other goods in your flagship which will slow it down), save the game (in case it goes wrong!) and start the first race. The quest there asks for fish and cider and gives you a +10% speed sail which you need. Start off by getting fish and cider production going, and head off to the beggar's island (central on the map, NW of the Corsair's Lair).
