A reach is a sailing term...If you catch a favoriable wind and can travel on a "broad reach" that is the fastest point of sail. " We made great distance and time on our last "reach"....".A head wind reuires one to tact several times to get to point B. This can double the distance required to arrive at your distination. Yes you can sail directly into the wind but it requires one to tact (zig zag) to get there. If you have a quartering head wind or a wind across the boat you can set the sail and the boat in a "broad reach" or a reach...My bet is this is where the term started....Yes I was a sailor but not a pirate....