Piracy

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Well the most profitable plunder is probably available on the Torcastan Sea. While the state sponsored privateer isn't really a thing, some national navies are willing to overlook piracy that avoids their nation's ships.
Sea trade is mostly a private enterprise by the merchant's guild, and as such they are mostly on their own for protecting themselves from pirates. Many employ ship board mercenaries, or even band together into flotillas of 6 or more vessels for protection.
A savvy captain can still make a living by preying on the smaller independent operations that ply the coasts.
If the pay/share of the booty is sufficient, you can find no shortage of former and current sailors willing to cast their lot and join a crew.
The penalty for piracy if caught is almost universally death by hanging. Many a wharf has a gallows right beside their customs house for displaying the justice dispensed to pirates.
No one has invented the cannon or firearms yet, so it is mostly small catapults, and ballistas, followed by ropes, hooks, and boarding planks. Shipboard skirmishes with melee weapons soon follow. Unless one uses fire as a weapon the ships themselves are usually seaworthy after an engagement and many crew would be happy to switch allegiance instead of risking a lengthy swim to shore (assuming they can even see one).
The best loot is generally from foreign ships coming to Iskander. One's leaving tend to be carrying local products and there is not much demand for them locally. learning the general pattern for shipping one can predict when there are plenty of ships to choose from, leaner picking in the off season, better to just drop anchor for the winter in some port where you can pay off the dockmaster to overlook your activities.
Everything can be sold. if merchants are shipping it to Iskander they have a good idea to whom they'll be selling and for how much. I would avoid trying to move large quantities of cargo, known to have been taken by pirates. To this end, cargo which can spoil is generally not a good choice, unless you have a open arrangement with someone to buy whatever produce you bring in. Precious metals never really go bad, so they can be stashed, and sold as needed, or used to fund crew wages, ship repair and upkeep. Some of the best hauls are textiles other than wool, and wine, as grapes just don't grow well on the islands.
A captured ship can add to the overall plunder, or be scuttled as needed if sufficient crew is not available to bring it into port.
If the ships we raid are foreign, the navy often looks the other way, or only puts in a token effort. They have ways of tracking ships, but aren't very efficient, as it takes so long for messages to travel. Usually they try to lie in wait, or simply patrol regular shipping lanes.
Good navy captains always vary their patrols. Oh, it's possible to pay the right snitch to give up information, but once a ship leaves port only those on board know for sure where it is headed, or they might, but a good captain knows that once at sea, the plan tends to need revision. They're given some leeway.
Mercenaries that can be bought - many of my own crew began as such. Mercenaries go where the money is best. And if no one survives to tell the story of their disloyalty, then their reputation is intact, besides if they're signing on to be pirates, their reputation is pretty much decided.
Hard to say, but Iskandeans are born to the sea as we say. Naturally attuned to the tides and currents as many islanders are. Other cultures have less need to be on the water, so they tend to be good fighters on land, but lack the legs for fighting on a tilting ship's deck. Aralian military are all paid mercenaries from what I hear, professional soldiers through and through. Still, my money would be on Iskandean's if the fighting will be ship to ship.

National Attitudes Towards Piracy

Persons

Kolm Dar-Ukys (pirate captain)
Mai-Lynne Ykel-Bitat (pirate hunter)

Stories

See Also