Complete mission walkthrough:
We'll start off by watching a short but interesting cut-scene. The game will give you a small hint here. As you've probably noticed, there's a guard nearby and you're going to have to take care of him in just a few seconds (#1). Make sure that you have read all the information windows. Once you've regained full control over Jack's movements, talk to one of the men standing here (#2). You will be rewarded with 200 gold coins for saving this guy from his cell in the prison fortress.
You should be able to find at least two barrels in this area. Destroy them, as they may contain gold pouches. Make sure that you have picked up these objects. Proceed to your right. Stand on the glowing point and press the action key (#1). As a result, you will dispose of this guard in a very funny way. You will also have to surprise three other guards, but we'll get back to it later during the mission. Keep moving right (#2). You won't have to explore the upper road, because you wouldn't find anything of interest there. Get ready for the "Jackanism" mini-game!
I guess it may surprise you a little bit, but this mini-game is going to be much easier than the one from the first mission of the game. You will be pressing similar keys, mostly ENTER (#1) and different cursors (#2). Also, even you make a mistake, you should consider restarting the whole level. The reason is you wouldn't have to repeat too many actions to reach the mini-game area. Once you've won the mini-game, destroy some of the nearby barrels (left side of the screen).
There are some crates to your left and near the bridge. Destroy them and collect gold coins. Now you should consider talking to a woman (#1). You will receive additional info for the 'missing husband' sub-quest. Make sure that you have chosen the first answer! Once this is done, head on to your right. Talk to one of the locals (#2). This man will grant you with a proposition to help him steal some rum from the tavern. You will have to agree. We'll get back to this mission in a short while.
Keep heading towards the right edge of the screen. Don't forget to destroy all of the surrounding crates. Once you've reached the square, you should turn right. There's a wanted poster here (#1). Take care of that small problem. Next, you should consider talking to a woman (#2). As a result, you will receive new instructions. These are going to be the main goals for this mission.
There are some new crates to your right. It's very important that you destroy them, because one of the crates will contain your first crab pendant for this mission (#1). You could also destroy other barrels, however they will only contain gold pouches. If you want to take part in the mini-game, talk to one of the locals (#2). Check the second screen if you want to know where he's standing. The rules of the game have already been described and you will be able to read additional hints once you've started it.
Now you should consider surprising two other soldiers. They are patrolling this area, however they won't attack you. You will have to be standing near certain barrels (#1; #2). Once each of the soldiers stops near the barrel you will have to press the action key. Sadly, you will have to wait for one of the guards a little while longer. Be patient!
Once you've taken care of all other problems, talk to the owner of a local tavern (#1). You will have to be giving correct answers in order to keep the conversation going. This will allow the other pirates to steal the rum. You should be choosing the first answer from the top. The only exception is the first part of the dialog. You will have to choose a second dialog here (#2). Once the conversation is over, you should go back to the man who's standing near the bridge. We'll get back to this mission once you've reached Tortuga.