Calypso, The City of Clouds

If the Plane of Air had a capital city, Calypso would be a strong contender for the title. This sprawling city sits on a series of massive cloudstone islands in a magically supported cloud that obscures it from casual view in the Labyrinth Winds. Ramshackle buildings, opulent towers, grand villas and terraces, and dozens of shops and stores lay haphazardly scattered about the uneven cloudstone streets of Calypso, and all manner of creatures live, eat, and die in the City of Clouds, which has become a lawless haven for thieves, pirates, and unscrupulous merchants.
The city is nominally governed by the Confederation of Calypso, a group of the most influential sky ship captains that call the city home, but they have passed only one law, known as the First Law, the makes Calypso neutral territory for the purposes of pirate rivalries. The law is maintained by no regular militia, and fights regularly break out, but they are between individuals with problems with one another, not ship crews fighting ship crews.
Several influential guilds and organizations in Calypso keep things running as smoothly as possible. The Guild of Mages are the first line of magical defense for the city, and they maintain the portals that lead into and out of Calypso with a tight rein. The city’s Guild of Thieves runs gambling institutions, protection rackets, and other activities considered unsavory in more respected places. The most powerful guild on Calypso, however, is the Guild of Shipwrights. These are the craftsman that make and repair the sky ships that support the activities of the Confederation, and this guild wields its power with tyrannical authority. Most residents understand that though the Confederation of Calypso supposedly runs things, it’s the Guild of Shipwrights that operates the in’s and outs of the city on a regular basis.

Government

Confederation of Calypso
There are only a few permanent settlements in the Plane of Air, and the cloud city of Calypso prides itself on being the most mysterious, at least to the outside. It is a city that sits in a permanent blue cloud built upon cloudstone that serves as the central base of power for the Confederation of Calypso. The Confederation is a loose alliance of pirate captains, each with their own sky ship, that call the city of Calypso their neutral home. Whatever blood feuds and ancient enmities exist outside, inside the bounds of the city there is a peace truce.
At least, that’s the idea. The Confederation does meet irregularly, usually only when the city is threatened by some force, and then its only the sky ship captains that happen to be close to Calypso at the moment that are invited. Each captain registered with the Guild of Ships in Calypso is entitled to a seat on the confederation council, which allows them to vote and pass laws as necessary. As the council is made up of murdering, thieving pirates who ply the air currents of the plane seeking treasure and plunder, little actual governing is done and the council has thus far only enacted one law. Known as the First Law, it is what keeps Calypso as neutral ground for all confederation members.
The cloud captains of the Confederation of Calypso range far and wide from their home, and encountering one in the wilds of the Plane of Air usually has no lasting consequences beyond dealing with the single pirate sky ship. Theoretically, the council could take some large-scale action against a force that attacked one of their members, but thus far no such concerted effort has even been brought forth as a proposal. The pirates seem content to raid on their own and return to Calypso, happy in the knowledge that the First Law protects their ship from deliberate harm.
Several members of the Confederation of Calypso have hired themselves out as mercenaries to other powers in the plane, such as Yan-C-Bin or the Prismatic Order. The Wind Dukes of Aaqa want nothing to do with the pirates, however, and Memnor the cloud giant god pays them no heed, though at least one cloud captain is a cloud giant scoundrel of dark reputation (Atheus). Other captains include an aarokocra sorcerer, an air genasi bravado, a gnome priestess, a grim tiefling thug, and a charming half-elf bard with a legion of loyal pirate followers.

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