Howard looks concerned
Even with the element of suprise, and assuming each man here has 1 ship they captain, i find it rather unlikely that we could pull this off-not without losing quite a few men or taking quite a bit of damage. The 2 ships that fire on the fort would in particular be on the short end of the stick-forts are not exactly soft targets-and a proper one would be able to fire back quite heavily. I wouldn't be surpised if the 2 ships put on hitting the fort end up sunk.
No offense but this plan sounds somewhat suicidal. 4 ships, even with the element of suprise would not have much of a chance against a fort, a port with guards, and royal navy vessels.