Dealing with Largo's Quest
It may not be obvious when you first meet him in the Crystal Fortress back in Caldera, but the Pirate and Thief Largo who you encounter in the jails of Caldera and Tacarigua will turn out to have a fair impact on your character and the game!
In Caldera you could pay him for information about the storehouse by the docks, but that information is really not worth the price you pay -- so you can easily ignore that interaction opportunity... The fact that Largo happens to be a Pirate/Thief Instructor turns out to be rather useful and important, since he can teach you some of the skills that you need in order to complete the quests that are required in so that you can break him out of jail...
The reason that he gets his own special section here is largely due to the fact that the different actions you are going to need to take with respect to Largo and his needs are fairly complex and really should be focused on exclusively until they are completed. That being the case, here is his section, and in it we will address each action by the numbers so to speak, starting with your meeting him in the Tacarigua Jail...
-- Largo's Woe --
When you arrive in Tacarigua it was on the ship The Black Betty, which was also the ship from Caldera that Largo was transported in. As you explore the village and port you will be surprised to discover that once again you will encounter Largo in a jail cell!
This time around he has been placed in the cell for causing trouble in the fields, where he was sent to work. The agricultural pursuits in Tacarigua all center around the production of sugar, which is then distilled into Rum, and the sugar cane production is largely completed using slave and prisoner labor, and it seems that Largo has made himself a disruptive influence in the fields with the other prisoners and the slaves to the extent that the powers that be here concluded that locking him in a cell alone was the smartest action to take.
When you talk to Largo he tells you what has happened to him since you last met -- that all of his possessions have been stolen from him by a guard whose name is Carter, and who is charged with overseeing the prisoners, and he details the meager list of his stolen possessions:
-- A Red Head Scarf
-- Black Pearl Earring
-- Leather Shirt
-- Worn Boots
At first the list of stolen kit is not really important, until you are offered a quest in which you can help Largo escape, which he offers you once he learns you have an interest in joining the Pirates on the island. You see it turns out that Largo was one of them! He knows them and he knows where they are located, and he can serve as an introduction to them for you should you like that. Of course you do, but before that can happen, you are going to need to help him break out of his cell...
To free Largo you will need to have acquired some basic lockpicking skills AND a lockpick -- happily he tells you about the Pirate Smith named Stone who can supply you with a pick -- but in order to obtain a lockpick from Stone, you will need to provide and show him proof that you come from Largo, and it is in fact Largo making that request of him. Largo explains that you will need to acquire either his Black Pearl Earring, or his Red Head Scarf, both of which are well known to the Pirates as being Largo's possessions and will certainly ID you and show that you are on a legitimate mission from the Pirate. Note that to complete the Pirate Clothes quest you need to recover all of the items that were stolen from Largo anyway, since you will need them to give to him after you open the cell to help him escape anyway -- and that means that you will want to replace with an upgrade any of the items of his clothes that you were using...
A duel with swords to obtain the stolen bandana from Riley
-- Obtaining the Proof --
Largo explains what you must do -- which is obtain the head scarf or the earring, or both if you are feeling especially adventurous!
The Red Head Scarf: Sold by Carter to the field warden, you can only recover this by heading to the cane fields and challenging Warden Riley to a duel. If you have already had some dueling experience with either Severin or Roquefort, you should be aware of how it works. If not, then this will be your first experience! Be sure that you have plenty of Provisions going into the duel so that you can heal as needed... Granted the Provisions heal over time, so you have to do a lot of Parry-Nine's as you fight, but it is a workable tactic.
The Black Pearl Earring: This item was retained by Carter because he likes it. It is therefore to be found in his pocket, and the only way that you can obtain it is to acquire some basic skills in the pickpocket ability, and then use them on him to obtain the earring.
As you are not very likely to have the gold that you need to obtain the Pickpocket skill at present, we can start out by exploring the immediate area of the port and village, the beaches, outbuildings, and the like, and completing as many of the local quests as you can manage, as you basically do all of the things you can do to earn gold. Once you have a few thousand gold, come back to this spot in the section of the guide!
-- Obtaining Training --
So, now that you have some gold head back to Largo and access his training menu, and have him teach you the basic Pickpocket skill. After you have acquired that (you should already have learned Stealth Sneaking from him but if not, do that too), save your game!
Now head to Roquefort and ask him to teach you basic Blades skill -- which will make you a much more formidable person to duel against with swords, and particularly with piercing weapons! Now save your game!
-- Obtaining the Items --
So our next step after saving the game is to head to the cane fields where we will find Warden Riley and challenge him to a duel! It is important that you actually challenge him to a duel and not simply attack him on sight, because as long as you challenged him fair-and-square, the other guards will treat it as an honorable combat and not interfere, and your battle with him will not cause aggro in town. If you just outright attack Riley though, you will gain aggro and kill-on-sight status with the guards there.
The process of sword duels is simple enough - you basically want to do enough damage to put him on his knees and cause him to yield to you, at which point he will give you the item you are seeking. To accomplish this you will basically want to assume a defensive posture, holding the Left Trigger to keep your blade in the parry-position, and wait for him to complete his attacks so that you can get a few hits in of your own. Obviously you want to limit as much as possible the damage that he does to you, so it would be helpful for you to at least be kitted out in the basics, -- boots, shirt, pants, and the like.
The duel will take anywhere from five to fifteen minutes, but should result in you standing over Riley, who is on his knees having had the snot beaten out of him! Once he hands you the Head Scarf you have obtained the second "proof" and good on ya mate! Well done! Now save your game!
-- The Black Pearl --
To obtain this -- now that you have the proper skills -- head over to Carter and get him drunk on Grog, and once he is drunk, pick his pocket to get the Pearl Earring. Simple as that. You should have some bottles of Grog in your Inventory - if not you can buy some more from the Cook.
Now here is the thing, at this point you have everything you need to complete the quest, but there are some other things we will want to do, including farm the money we need to further upgrade our character, so we are not going to be heading directly to the Pirates Den but sort of in that direction mates...
-- Gathering Intel from a Slave --
At nightfall head to the hut where the slaves sleep and talk to Asad, who will tell you he is hungry. Give him one of your Provisions and that flags and completes the quest A Hungry Slave. So you did a good deed -- fed Asad -- gained some Glory, and you learned exactly where the escaped slaves are. You also learned hat they will go postal upon seeing you and do not care who you are... If you encounter them, he explains, you are going to have to kill them.
You can get information from him about the graves of his ancestors, which include stone tombs filled with treasure! He also warns you of the wrath of his ancestors as well when graves are robbed... If you have not figured it out, he is talking about Voodoo.
I am in no way making any moral judgments here but it sounds like you are going to have to kill these guys when you find them anyway, so if you accepted that quest you cannot consider it having done a bad thing, things being the way that they are. That is all I am saying about that...