My wife decided to take the day off and go visit her parents. This gave me the chance to indulge in an activity in which I am not normally allowed. An activity that every red-blooded male loves to indulge. Not porn, but Jackie Chan movies (this time). I rented the movie Project A and was struck with the great piratical gaming ideas that could come from it.
Every fantasy campaign eventually pits the adventuring group against some blood thirsty pirates. The secret hide-out of Sam Lo Pan in Project A is a perfect example of a pirate hideout. To start, the hideout is located on a secluded and secret island that the local authorities can never quite pinpoint. If you are going to play the pirates as reasonably intelligent, the party first needs to find the island. How you decide to do this is up to you. The characters could pay off an informant, or attempt to join the ranks of the pirates themselves. There are other ways I'm sure, but these are probably the first two ideas most people will come up with. The island itself needs to be defended in some way. A hidden cove is good, but how about having pirates with bows stationed behind blinds on the sides of the island? This way, they can watch for arriving ships and be ready for any attacks. If the pirates have access to catapults or ballista, they could also be hidden behind blinds to surprise anyone approaching the island.
The island itself should be patrolled by members of the pirate gang. How tough these roving guards are is up to the GM. Personally I would make each of the guards one or two levels below the average level of the party. This isn't to make things overly easy for the adventurers, but since the average town watch is populated by 0 level man at arms, why should the pirates have really strong guards. The tougher pirates will always be inside the hideout anyway. Only the weaker and less experienced pirates would be given the guards duties.
Project A had a wonderful set of cave complexes inside the island that the pirates used for their hideout. There were the obligatory twisty and narrow passages and the one, great hall sized cavern for the general meeting place. The main hall in Project A was paneled and floored in wood, so as to give the illusion that everyone was still on board a ship. To me, this is a great bit of atmosphere for the pirate's den. A particularly fun loving GM could use these fake walls as locations for hidden guards, or entrances to the Pirate King's hoard.
Within the caverns, there should also be a room or two set aside for prisoners. Perhaps the King's daughter has been taken prisoner, or his admiral. Both of these provide hooks for the party to be taking on the pirates rather than supporting their local law officers. I would also provide one basic treasury in the regular part of the cavern complex, but keep the really good stuff hidden somewhere special. Your average Pirate King isn't going to leave the really good stuff where his men can get at it. He, especially, is aware that his men are nothing more than a bunch of thieves, rapists, and cutthroats!
Of course, there doesn't have to be a cavern complex that the pirates are using on the island. Perhaps there is a natural valley on the island, that the pirates have built their stockade within. Even here, I feel that designing the interior, at least, of the buildings to resemble the interior of the ships is the way to go.
The Pirate King is an NPC that needs to be fully built. Take as much time to create this character as you would to create a character of your own. This is a pirate that has been able to fight his way to the top of a group of equally nasty people. Brute strength isn't enough though. Even though the Pirate King will have had to fight his way to the top, he also needs to be a cunning and intelligent person. No matter how strong of a person he is, the rest of his pirate fleet isn't going to follow him to the bathroom unless he is planning successful raids. If the party that will going up against him is roughly 5th level or higher, I would make sure that he has some spellcasting ability along with fighting prowess. Most pirates come from a rogue mold, but there isn't anything against having a warrior pirate. In fact, it could be the Pirate Kings fighting abilities as a warrior rather than a rogue that has allowed him to ascend to the top. As far as spellcasting, either mage or cleric would be fine. If the Pirate King is a cleric of some kind, you don't, as GM, necessarily have to make him an evil cleric. A neutral Pirate King could be just as nasty and cunning as an evil one.
These are just my quick jottings concerning including pirates in your campaign, but I hope they are useful to anyone out there. I would love to hear about any other suggestions that people might have. I have always loved taking my campaign out to the high seas for a month or two. Comment below, or email me at firstname.lastname@example.org.