The classes and main rules are based on Arnold K's GLOG, mutated and altered as usual. The sailing, exploration, and cargo rules don't use the GLOG directly. If you want more GLOG content, check out the G+ group here.
Settings and IslandsAll files are included in this Google Drive folder. If I add any more, I'll update the maps and post them here. Adding more islands to this setting is trivial.
1. The "Core" region - The Merabaha Islands
Originally, Hot Springs Island was going to be added to this chain, but I decided to go with a more low-magic setting. HSI is excellent but it's got lots of planar politics and magic all over the place. The Lapis Observatory made its way onto the Isle of Dread, and I'll definitely use bits and pieces of the book in other locations.
Further ReadingRichard G's Countercolonial Heistcrawl notes (this post and others) is the best place to start. It covers everything I could possibly cover in an introductions and more: why pirates work, how to disrupt or manipulate nations, what a pirate state might look like, etc.
Dunkey Halton's Comache Hexcrawl notes for similar ideas and approaches.
Jeff Russel's "The Sages Say" monster generator is good for sea monsters and other weird beasts.
Dunkey Halton's 1d100 Island Encounters in the Islands.
Sheep and Sorcery pirate tables and sea monster tables.
Unlawful Games' Barrier Island Generator
Cacklecharm's Ship Name Generator
As per Lungfungus' request.
The classes have been tested. Not all the Weather Witch Workings have seen play. Ship combat has been tested, though I may still fiddle with the numbers. Pirate Democracy rules were tested in a completely different game with plenty of interesting consequences.
I'll probably put up a separate PDF of ships, upgrades, and magic items at some point.