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We did our first pirate hunting job yesterday and it ended up being pretty interesting. The party took on a schooner and a sloop in their brig and managed to pull off a very impressive maneuver. The pilot managed to go hard port while full ahead at maximum speed, passing the DC 40 check by 1 point and the master gunner successfully broadsided the sloop's sails, disabling them until they got their oars out. Then they all teleported onto the schooner, killing over half of them with chain lightning. The captain threw himself overboard and got the attention of the gargantuan Sea Serpent the pirates had been sacrificing people to and the PCs managed to kill it off, though it nearly instagibbed one of their sellswords.

The crew of schooner surrendered and the crew of the sloop tried to make a getaway after seeing their sea serpent get turned into lunch meat, but they didn't have much luck.

So, first set of code breakers down, sacrificing people to sea monsters is bad, even for pirates.

Kat's Grace, simple, elegant and extremely haunted.

My game is a combination of a few different nautical settings, primarily Freeport but including the Shackles, and it's taken on a sandbox element recently. The PCs have a Letter of Marque from the Captains' Council empowering them to hunt specifically pirate ships, but being proper Freeporters they don't want to damage their reputations, so they've decided that they're only going to hunt pirates who openly defy the pirates' code and are generally disliked by even the pirates of Scurvytown.

They've chosen to use their time in this sandbox (aside from their personal ambitions and goals to which their hard earned gold will be used for) to go on a pirate hunting spree and I don't want for it to be a series of repetitive ship encounters.
What I need are suggestions for how to make these ships and their crews varied and interesting; what kinds of deeds and characteristics set them apart from regular pirates? Becoming hated even by pirates is quite a feat so I imagine these must be the evilest of blackguards.

I've only managed to come up with one which I'll give as an example, a ship called the Nightchild that plies Darklight Lane only in the dead of night, descending upon it's prey with almost supernatural stealth and swiftness. This unholy vessel is crewed by enthralled vampire spawn and their vampire officers. The captain is a dread vampire and a terrifying swashbuckler.

Not all of the ships need to be something extraordinary like that but having a wide variety of interesting crews would help me greatly.

Thanks for your input!

(If it helps, the party is made up of level 10 gestalt characters.)

Thanks, I appreciate your reply!

I'm curious about the Plane of Shadows on a few points, just wondering if anyone has any insight or ideas.

-Are the denizens of the Shadow Plane (not including fletchlings) just warped mirrored images of their counterparts on the Material Plane? I assume that the people on the Material Plane exist in the Shadow Plane but as alternate reality versions of themselves, right? If so are they really just a different them but with minds and souls of their own?

-Is it possible that denizens of Material Plane visiting the Plane of Shadows would run into themselves from that reality or does it not work like that?

-I get that the Shadow Plane is essentially just a skewed version of the Material Plane but does it function the same? Do people still run businesses, travel, adventure? Or do only Fletchlings do these things while the shadowy images of Material Plane inhabitants are like creepy backdrops?

Anyway, these are the questions I had for now, any thoughts, ideas, answers or suggestions are welcome,

thanks!