This weekend
the expedition into the weird weed sea around the
Doom's Wake continued. After the unexpected assault last time (for the pirates, but also the PC's actions for surprisingly effective to me as the GM). The pirate's get on a little better footing. Good rolls and strategy (involving a druid transformed into a bear and a cloud of daggers in front of a door) let the PCs the prevailed against lieutenants shark-faced Squalo and starfish-headed sorcerer Astero, as well as a dozen nameless pirates. It did not, however, prevent the pirates from informing their compatriots the PCs were coming.
By luck as much as design, the player's avoided a confrontation with the grim matriarch of the pirates, which very likely would have resulted in their deaths--and probably unhappiness with the adventure. This was not an old school crowd inured to the total party kill. The warnings by NPCs made them more curious than afraid, but in the end the learning the prisoners they sought were actually held elsewhere made them move on.
On the next assault, the pirates had the high ground and a warning the PCs were coming. There was even an ambush by the lamprey-faced lieutenant Handsome Blut with a wight's drain attack! In the end though fate left Blut with really bad rolls and the superior numbers of the PCs forced him to flee, badly injured.
The victory at the prison ship was more attributable to good player tactics. They had an approach over the weeds that left them easy targets for pirate crossbows, but they used an obscuring mist and minor illusions to improve their odds. The pirates were also beginning to feel the loss in their numbers.
In the end, the prisoners were rescued, but by negotiation, not force. Some pirates were left alive to continue their raids, and the source of the pirate queen's particular interest in Ligeia Marsh, adopted daughter of Clegg Hobtree, major of the Raedel, remained a background mystery.
One of the player's (an experienced GM of other games) suggested weakening the mook pirates, and increasing the power of the more colorful lieutenants. Uping the lieutenants power is probably a good idea, though the pirates were probably about as weak as they can get. The difficult with them is just a nature of their number and the D&D system. It may be I need to think about the staging of the encounters though, so perhaps fewer mook pirates might be necessary.