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I'd suggest using another sailing fighting tactic rather than trying to scope out a "rumored" easy ship.
Try circling in front of their bow, since they're not manned ships (like navy) and thus cant shoot foward. Stay off their port & starboard, and you're good to go.
Or... there's always the "crew with those who have bigger ships" option - and let them do the hard work of sailing - the quest only requires you to be along for the ride.
-Captain
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