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1 - Governor Blackeye

You can do two things with Governor Blackeye: you can buy pirate booty from him for 100 gp, and you can convince him (by paying their bail or by being persuasive) to free the prisoners from his jail.


2 - Grubby Convict

You won't be able to get the grubby convict out of jail. If you talk to anybody about him, they won't even remember what he did.


3 - Prison Guard

The prison guard will sell you some pirate booty for 100 gp.


4 - Longneck Langer

If you talk to Longneck Langer, you'll learn that he's in jail because he's "not piratey enough." There are three ways to free him: by persuading Governor Blackeye (#1) to free him, by paying Blackeye his 10,000 gp bail, or by making him more piratey. For the latter, you'll need to free Falstaff the tattooist (#5) from jail and then use his I.O.U. to give Langer the Jolly Roger Special.


5 - Falstaff the Tattooist

If you talk to Falstaff, you'll learn that he was put in jail because he gave one of Governor Blackeye's daughters a racy tattoo. He'll ask you to get him out, and he'll offer you an I.O.U. if you succeed. However, although the conversation will bring up picking the lock to his cell or persuading Governor Blackeye (#1) to free him, those options don't seem to be available, so if you want to get Falstaff out of his cell, you'll have to pay his bail of 1000 gp to Blackeye.

Once free (and after talking to you again), Falstaff will return to his tattooist shop in Spindrift Town, and you'll be able to use his I.O.U. to get a free tattoo. But note: You can also use the I.O.U. to help Longneck Langer (#4) become more "piratey." If you do that, then you'll have to pay 1000 gp for a tattoo.


Exits:

1. Exit to Spindrift Town.
2. Entrance to the Sewers.