This one is a bit of a pain. Click 'read more' for a detailed explanation.

Deal with the first five schooners. Then, essentially, disable the sails, position yourself at the front of the ships, and open up on them. It should reveal the powder kegs

Neftali Franco writes in the comments (thanks):
YES!!! I just got it You have to aim about like 1/3 of the shot and focused to the front side of the ship they also have to be disabled for easier shooting and I think also a little bit of luck. Well good luck:D

Optional objectives:
Sink ships by firing on their powder stores - 3/3

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