From the Wiki entry on Elizabeth Shaw's Disappearance:
My fleet consists of the Black Pearl, the Mefisto and the Sovereign of the Seas. Ever since Pieter Boelen supplied the code fix which gets you the uncursed version when you board it at the end of the main quest, the Black Pearl has been my main ship for general pirating. So that's what I was sailing the first time I met the Flying Dutchman. Ignoring the above advice, I engaged, with the Sovereign of the Seas providing fire support. By the time the battle was over, the Flying Dutchman was down to about 50% damage and didn't want to play any more. When one side stands its ground and the other side uses its special ability to "sail" straight into the wind and run away, it's reasonable to conclude that the side which ran away was not the winner.
After reloading a game saved shortly before this battle, I swapped ship to take command of the Sovereign of the Seas, a somewhat less nimble ship than the Black Pearl - normally I only take over this ship if I'm about to go up against something even less nimble, e.g. a fort.
Then I went to Cayman to face the Flying Dutchman again. Most of the battle was fairly dull and one-sided. The Flying Dutchman may have a silly number of damage points but it doesn't have a silly number of cannons or masts, and it wasn't long before she was minus her main and mizzen masts and down to about 5-6 guns and 5-6 crew. So when the Flying Dutchman did return fire, it was infrequent and ineffective. Meanwhile I was still pounding her with most of the broadside of the Sovereign of the Seas, having to raise battle sails, pick up a bit of speed and then strike all sail so I didn't whiz past the Flying Dutchman. (You'll probably never see me use the word "whiz" in the same sentence as the name "Sovereign of the Seas" ever again.
) Eventually I ran out of cannonballs, by which time the Flying Dutchman was down to a few percent of hull, so I started firing whatever I had left - chains and grape. Then I ran out of powder. The Flying Dutchman was now down to about 1-2%. I was going to sail up to one of my other ships, relieve her of her ammo and finish the job, but the Black Pearl saved me the effort. With one well placed salvo she knocked off the last remaining percent, and Davy Jones went to his own locker. (Which didn't stop him from showing up in the port and giving me a headache.
)
Invincible, eh?Flying Dutchman ( it is invincible – run away ) attacks you outside Cayman Port
My fleet consists of the Black Pearl, the Mefisto and the Sovereign of the Seas. Ever since Pieter Boelen supplied the code fix which gets you the uncursed version when you board it at the end of the main quest, the Black Pearl has been my main ship for general pirating. So that's what I was sailing the first time I met the Flying Dutchman. Ignoring the above advice, I engaged, with the Sovereign of the Seas providing fire support. By the time the battle was over, the Flying Dutchman was down to about 50% damage and didn't want to play any more. When one side stands its ground and the other side uses its special ability to "sail" straight into the wind and run away, it's reasonable to conclude that the side which ran away was not the winner.

After reloading a game saved shortly before this battle, I swapped ship to take command of the Sovereign of the Seas, a somewhat less nimble ship than the Black Pearl - normally I only take over this ship if I'm about to go up against something even less nimble, e.g. a fort.



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