Also known as the “Liberty Isles.” These islands are difficult to navigate, with thousands of ready-made hiding places for a ship. They were fortified in the war with Mord-Stavian. Some of those fortresses crumble in the humid heat, others have been shored up and refurbished by pirates. A few settlements draw traffic, but most are designed not to. The liberty comes at the price of safety.
Not-Sicily/Mediterranean. Classic age-of-sail high seas treasure hunting piracy and trade ships, rife with letters of marque and reprisal for privateers and romance novel specimens of manhood and womanhood striding the rolling decks. The islands are stuffed with places to hide. Sometimes ships will drop anchor just to visit a settlement comprised mostly of taverns and houses of ill repute. Ghost ships rise from the depths, and also sail from the south. The law is fragmented between sparring nations in these waters, so lawlessness is mostly kept in check by well-armed traders.
Pirate Countess Isolda Tarmapp rules in the sense that she adjudicates disputes and maintains treaties. The Pirate Count/Countess position was founded by a pact between King Vorhiax and Commodore Duhnell, sealed by Mother Lothak herself. Certain powers were granted the Pirate Count, so the position came to have the respect of all pirates (and others) who sail these waters. Outside of that, cutthroat rule of the strongest and most cunning is the standard order.
Utterly lazy and without character, murdering thieves, almost sub-human degenerates that must be whipped into shape to do anything. The collected refuse of the rest of the World Between. Superstition has overtaken reason completely. They have no concept of honor, the only ones with education are the worst of the lot because they’ve fallen so far. However, no one can predict weather like they can, and they all have the ability to summon sea demons. Every pirate knows where at least one booby-trapped treasure is hidden, and any treasure a pirate gets will be hidden in its turn (or spent on women and wine.)
Techniques for brutal punishment and torture. Finest techniques for streamlining and repairing ships with minimal facilities. Weather magic. Cheapest grog in the world. Most jaded prostitutes in the world.
Plotter’s Blood Bay. Tucked out of the way, but not too out of the way, this port tends to harbor those on the wrong end of usurpation and betrayal in the Iron Principalities. Sometimes more exotic ousted nobles or royals will hide here. Everyone knows the Commodore and his line are of royal blood, but no one knows which throne they may someday claim. Commodore Bytslaan protects those seeking political asylum in Plotter’s Blood Bay, as long as they sign the Refugee Blotter in his castle.
The Ramshackle. Spread across the wide mouth of a bay, there are literally hundreds of run-down public houses. They have houses of ill repute, taverns, markets, mercenary auctions, press gangs, markets to buy and sell the dead (animate or otherwise), and every kind of debauchery that could abase you. “To the Ramshackle!” is a battle cry known across the sea. It means the crew demands shore leave, or the infamous pirate settlement is under attack and everyone should come to its aid.
Wrecker’s Point. The unpredictable rocks around this settlement have assured that no navy has successfully taken the city. A small, easily defended port on the other side of a ridge allows ships to drop anchor and send delegations to the Point, where the Pirate Countess holds court. If she doesn’t like what you have to say, you won’t make it back to your ship. A court sprang up around the Point; any politically aware pirate captain wants to know who is saying what to the Pirate Countess. A few spies from other factions are also tolerated for her amusement, granting her the ability to communicate with governments by passing intelligence (or counter-intelligence) as she sees fit. The settlement got its name from rogues who set up false beacons, guiding ships onto the rocks, then killing any surviving crew and harvesting whatever floats from the shipwreck. These heartless criminals are called wreckers.
Shrine to Mother Finn. This temple to Sothak, Our Lady of Sharks, is on a crumbling promontory off Sharkbite Bay. It is occupied by sea witches, and guarded by shark men. Oracular pools there are said to be able to control weather and spy on anything touching the water in the Sea of Sothak. Rumor suggests they only accept payment in shipwreck treasure and human sacrifice.
The Shell by the Sea. After the Banishment War that tore Caligari in two, King Vorhiax came to rule a powerful port in the Crook Mountains. He desperately missed the high art of Caligari, especially opera. He found an acoustically perfect location on an island, and developed it into the Shell by the Sea, a fantastic opera house. To protect it, he made a deal with the most powerful pirate in the Isles, Commodore Duhnell. In exchange for protecting the Shell, the new Pirate Count would have some elemental authority to rule the other pirates and compel a degree of order. The opulent concert hall is strangely safe, and people of all kinds meet there to witness fantastic performances by performers from all around the Sea of Sothak and beyond.
Order of Consecrated Tenebriates. They are said to lair in the shadows in the center of four islands, moving through cracks in the stone to step in and out of their shadow lair. Their purpose is unknown. Legend suggests they gain their sustenance from drinking the shadows of their victims. They have a “diplomatic outpost” on the Black Lagoon, a small port where you’ll be found by their people if you ask around.
Tower of Zzorch. These towers can come and go in the mist and the night, bringing with them a faint red glow in the dark or the fog. Legend suggests the cultists and demons of Zzorch corrupted some towers of the Eladrian and now use them to move about the Isles. Zzorch is blamed for the spontaneous change to orc that is more common in the Isles than elsewhere. No one knows the purpose of the cult in the tower; not even its name. Those who investigate do not come back, or do not come back unchanged.
A Mother’s Love. While Father Sothak rules the sea, Mother Lothak has adopted this island cluster as her own playground (according to legend.) Our Lady of Sharks rules the pirate roost, further diminishing chances of law being imposed in the islands. The Demon Queen hates humans who worship gods like the one that defeated and wed her, and she hates other demons, so it pleases her to disrupt shipping and spread pain and fear. Bitter souls seeking revenge are drawn here, and may find mutually agreeable terms with Our Lady of Sharks for darkening the world.
The Death Fleet. Thousands of years ago an undead navy engulfed these islands, and some remnants of that past remain. Pockets of undead power, lingering spirits, and shambling skeletons still carry out dark purposes. Their numbers have been bolstered by refugee necromancers, secret agents of Mord-Stavian, and the restlessness of the sea infecting the islands. Some undead rise spontaneously here, and in sufficient quantity, undead energies can raise whole ships.
Nest of Demons. Demonic influence is so powerful here that those involved in marauding, or breaking vows, or other evil acts sometimes spontaneously become orcs. Most are so far gone they don’t care. Sometimes it happens to a whole ship’s crew at a time, and they murder and eat anyone aboard who doesn’t change with them.
The Code and the Vows. Making promises with pirates means giving them a bit of your essence. If you break a deal in the Isles, there is a good chance a curse will find you. Or a monster. Or you will change into something you’d rather not be. Still, rogues and miscreants risk it and break deals all the time. There are general guidelines for something like honor, but it is quite flexible as needed.