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It's possible to do alone, my first pirate, I did it alone... every barrel & crate, I just tried as close as possible I could get between the wall & the barrel/crate & made sure NO navy or eitc dudes were looking in my direction & hit shift. It was painfully long to wait until everyone was not looking in my direction, but hey it worked. Can't remember how I did it the 2nd time. 3rd time, I had a friend be my bodyguard & hitted everyone with flamming skull pretty much LOL.
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