I think I would have lasted about six months before I lost it. My skin is too delicate to survive constant exposure to the elements, I enjoy the feeling of good mattress and clean, DRY sheets, I bathe far to frequently to be considered a pirate, and I have an unrelenting need to feel the ground beneath my feet and the wind on my face when I run each morning.
No, I'd bail out at the first opportunity. Rum and gold ain't everything. Gunpowder? I've got some in the garage. Cannon? I have several small, hand-held cannons of various calibre. Bucket boots and a tricorn? Don't really need them. Piratical attitute? Probably not. Sword? I have one, thanks. It looks nice on the wall of my humble abode.
The opportunity to be a pirate wench? Oh, I think I'll pass.
Freedom? That would be a state of mind, not a thing or a place.
What am I doing here, then? Just hanging around to irritate the rest of you, singing all the while:
Arrgggh ! And Yo-ho! Yo-ho! A pirates life for me !!!