I would never do that in a campaign as I have too much time invested for the risk. In reality, the risk would be death, so Kaleuns never took that chance. The issue with risk in most games is that your life isn't really on the line, so it's easy to make, and get away with, stupid choices.
But when bored during single missions, I have engaged destroyers with the deck gun. I will surface, get a range with the UZO, and fire away. Your best bet is to hit the bridge as afterwords it seems that the accuracy of their main guns go down a lot.
Once I managed to engage two destroyers at the same time and destroyed them both in this manner.
PT boats: Now those are hard to kill....too small, too fast, too maneuverable.
