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What I do when Im sailing alone and want to take on some bigger flag ships is this:
After I grapple them I go on a cannon and shoot the guys that keep popping up on the deck.
You have to be careful to not hit the ship too much if you can help it. When the timer gets under a minute.. then hit the board button and go on over. This tends to get rid of a lot of the crew on that ship and make boarding easier.
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