Greetings fellow fantasy wargamers.  I am developing a world for my next series of adventures.  I am taking my own advice and using a map of England and Ireland turned upside down and moved to the mouth of the Mediterranean Sea as the land setting.  The main island of England is occupied by Elves in the North (between London and Birmingham), nomadic tribesmen on the eastern coast (Wales) and Dwarves in the South, which is covered with mountains (Scotland).  This along with an uninhabited Ireland was the status quo through the end of the first age.  Nobody knew anything about what happened on the west coast of "England" because there is a mountain range that runs along the western side like the Andes mountains run along the west coast of South America.  Neither the dwarves nor the nomadic men (think American Indians) have any naval presence, only the Elves.  The Elves have a seafaring tradition that allows them to remain connected with other Elven nations.  They wish to remain apart from men through the first age.

At the dawn of the second age, a beat up pirate ship and crew arrive on the west coast of "Ireland."  They refit their ship and return to the known world where their highly respected and charismatic captain convinces a handful of other pirate ships to join him in journeying back to establish a pirate base on "Ireland."  They have no idea initially how large the island is, but being uninhabited and full of timber they see it would be a great base.  It is also unknown to the authorities, which are considered Lawful Authorities.  The pirates are attempting to establish a Chaotic Nation with deep sympathies for Chaotic Evil motivations.  After establishing a ship repair facility and a town on the west coast, the first captain sets up a special pirate nation governed by their principles.  It is a society that values naval warfare in an era before the cannon.  He commissions a second and third city and shipyard to be built, one near the northern west coast and the other toward the southern west coast to supply his fleets.

The middle class in this society are ship hands, lower level officers, sail makers, carpenters, rope makers, artillery engineers, architects, cabinet makers, blacksmiths, metal workers, weapon smiths, jewelers and folks like that.  The lower classes are men unsuited to piracy and become laborers, farmers, woodsmen and the like.  The aristocracy are mainly former and current ship captains and quartermasters.  "Retired" pirates become fishermen and considered middle class.  It would be unthinkable for a pirate to retire and become a woodsman or farmer.

This society would need a substantial presence of wizards for two reasons.  For combat at sea, they would probably employ wizards throwing fireballs.  For other needs they would employ wizards that could provide long distance communication and divination to protect their fleets and find the best cargos to raid.  The head of this society of pirates is laying the groundwork to establish a permanent pirate nation and he is thinking long term of what he needs to make it happen.

Combat at sea has not yet developed in a significant way as a theory.  Magic users have not been employed in any significant way in naval warfare through the first era.  It is the establishment of this pirate nation and the push for a real navy that has ushered in the Second Age.  Before this event it was all about land conquest and there were no significant navies only better prepared merchant vessels.

I would like to hear any constructive ideas on how a pirate society would develop.  I would also like to know if anyone has ideas on naval warfare or is this pretty much handled as an abstraction in D&D.

I plan to develop this simply as a history of the Second Era because the action in my campaigns will occur in the Third Era.  The early second era will be the establishment of the pirate nation on land and at sea with an organized navy.  The later second era will involve the pirate nation discovering the Elves, Nomads and Dwarves living on the island next to them.  Additional races will be introduced into the mix as a result of the pirates employing mages.  The mages will lobby to introduce ferocious races onto the other island to sap their strength so the pirates won't have to invade to maintain supremacy on the islands.  This plan will not work out as the pirate mages planned and so the setting for the third age will include any number of conflicts as nations war with one another.

The elves, however, do have a strong naval tradition, and once the pirates make a nuisance of themselves because of their hubris the elves will show them what they know about naval engagements.

You are talking about pirates but have you considered vikings? Vikings are much like pirates.

Thanks.  I have thought of Vikings.  I figure anyone that develops a history of the islands will think about Vikings too.  My intent for the Vikings is to have them visit the islands and become one of those aggressive races but that event happens apart from what the pirate mages attempt.  I was thinking about having kobolds, goblins, orcs and hobgoblins are introduced to the island this way.  I could place Iceland near enough for them to come from there, or I could have them come from the direction of Africa.  In the latter case they would likely become a plague to both the pirates and the other races.  Historically the pirates came from Denmark, Sweden and Norway but I think having them come from Iceland is plausible enough.  I appreciate the help.

As I flesh out more details for my pirate culture it is becoming more and more similar to our ideas of the Vikings.  It may be that when I am done the Pirate Confederation may differ from the Vikings in that they raid for profit at sea, and the Vikings raided on land.  It is becoming very difficult to describe how a coherent pirate culture can exist with their collective attitude for strong independence.  It is also beginning to sound like a Guild with rules and price fixing.  For a short time I thought of how it might be similar to the 'convict culture' of Australia, but it isn't shaping up that way right now.

It sounds like historical setting wise this is pre-age of sail ships. That means that you have caravels, longships and ships not unlike the ancient greek ships. Seeing as you are going for older designs. You have lots of oar powered ships. Do some searches for ancient mega ships, multi-hulled ships, and ancient Chinese superships you will find some fun inspiration for non-age of sail ships and warfare. 

Thanks Pastorbarndog.  I was thinking that this will be the case that oar powered ships will be part of the mix, but I know there will be sail power too, but nothing as sophisticated as a square rig.  I was thinking that the Elves will be sailing gaff rig schooners and these will be the most sophisticated ships on the sea.