Cover a specific boat if you need to beat that boat.  Don’t forget about the rest of the fleet, though.  Two boats engaging in covering maneuvers can be slow, and the rest of the fleet can easily sail by.  If you’re in the lead, you should usually be covering those behind you – otherwise they may find better wind.
The concept of herding the fleet (or a single boat) involves loosely covering you’re opponent when he’s going the way you want and tightly covering him when he’s not.  See http://www.sailingworld.com/from-the-experts/tactics-and-strategy/staying-ahead-on-the-final-beat-48736.html for a more detailed description.
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