Oh Lordy, no....can't do that. I was in Soper's at the C&I office when someone did just that. The Immigration officer freaked out and made all kinds of threats to the parties involved. Doesn't matter if you take a mooring, anchor or not.

Drop him in Leinster, and call him a cab....it's easily accessible by road. Ferries on the hour from Cruz Bay back to Red Hook.