Wondrous item, legendary (requires attunement by a creature of non-good, non-lawful alignment)
“If I only had the cap – then I would be the cap!”
The wearer of the Cap gains advantage on wilderness navigation rolls at sea. In addition, the loyality of any crew aboard a vessel commanded by the wearer of the Cap is determined using the Cap‘s Charisma score instead of the wearer’s.
Sentience. The Cap is a sentient chaotic evil pirate’s cap with an Intelligence of 10, a Wisdom of 12, and a Charisma of 24. It has hearing and darkvision out to a range of 120 feet.
The cap can speak, read, and understand Common, and can communicate with its wearer tlepathically. While you are attuned to it, the Cap also understands every language spoken by any crew member of a ship you command as long as you are on board.
Personality. The Cap‘s purpose is to raid and plunder the world’s oceans as a pirate captain. If it spends more than a week at sea without raiding or more than a day on shore, a conflict between it and its wielder occures at the next sunrise.
Based on a concept offered by yandere: “Staying with the idea of the pirate hat. A magical pirate hat, which, after being worn for a certain time, will take over its wearer to go out to sea again under its own name.”