 In many shots the film skippers (Will, Morgan and Jack) can be seen  driving the boats from the leeward side while beating to windward.  In reality, most of the time skippers drive their boats from the  windward side, mostly to help keep the weight on the windward side  and also to give themselves a better view of the incoming waves so  they can steer a proper course around them. The reason for putting  the film skippers on the leeward side was so that the real sailors  could control the boat from the windward wheel while remaining  mostly out of shot (you can see their legs occasionally in some  scenes.)