Let's see... The White Ship sank in the English Chanel in the late 11th/early 12th century, drowning (among others), Henry I's heir. It was (apparently) sent to the bottom by drilling several holes through the hull. This, by the way, set up the civil war that followed Henry's death which lasted some, what, 20 years?

The period the event is set in makes a huge difference. When one considers that naval design of the late 16th century (roughly Hank VIII - Betsie I) was beyond the 11th/12th century model, but no where near whe it would be during the huge leap forward by the end of the 17th century, the answer is "maybe".

A couple of items mentioned above were common later on, but would have been radical innovations in the time that the original question was posed. Yes - fothering could stop serious damage. However, this was still quite new in the late 18th century and rather few ships had this done successfully before, say, 1780 or so. Also, copper sheathing was the great secret weapon against both worms, limpets and weeds on the bottom of ships hulls. Again, this was an 18th century innovation that was not wide-spread except on major capital ships until the later half of the century. (I forget the name of the first-rate that sank in Plymouth Harbour taking most of her crew with her. Seems when they added the sheathing, no one checked to see if the hull was sound to begin with. The whole bottom fell away from worms and rot. Oops.)

Now then, consider that most "war ships" of the time were actually merchant ships that had extra cannon added with reinforced planking an supports. Except for relatively few custom-built ships that were intended to be war-ships, the three-feet of oak plank was more likely 12-18 inches or less.

And so, Rick, given those things, I think the answer is a resounding "Well, depending on the type of ship this thing was, size, time period when she was built, and by whom, a determined cabin boy with a thing for the captain's daughter might possibly be able to sink a ship if he was very lucky."

She'd better be interested in him as well, or he'd be best off not wasting his time. ;-)

Cheers -

Pete