Go to any shop and ask to talk with them. An option will appear that asks the owner if he has any supplies that he needs delivered. If you do this with bigger ships you can get at least 30,000 dollars a trip. All you have to do is travel to another island of his choosing and deliver the goods to that islands store. I have 4 battleships and I have gotten up to 190,000 dollars for just one trip.
Easy Money: take two
While ferrying goods between islands is a good way to make a profit, there is another. It depends on your Commerce skill. When hiring an officer, simply talk to him and say that he's charging too much. No matter what he does (lowers his price or says he's worth it) refuse and once again tell him he's charging too much. Persistence pays off, even if it seems he won't lower any further, give it time and he will. You can lower them into the NEGATIVE numbers, and when you hire them they will pay YOU. I've pulled off 200,000 gold on one officer with this trick. NOTE: Your Commerce skill comes into play when they lower their prices, a formula would be CommerceSkill x 100 = lowering price. So if you have a Commerce skill of 1, they will lower it by 100, 2 is 200, 3 is 300, and so forth.
Pirates of the Caribbean
You can add more than one person onto your other 3 ships and all of their scores will stack with that ships captains scores.
There are two different ways to do this
1) On the Open Sea screen (where you can see all of your ships) get close to another of your ships and a swap cargo icon will appear. Go into the swap cargo menu and there is an option to switch captains. Under this option there is a screen that has 4 slots, one of them is the captain of that ship. Click on one of the other 3 and then assign passengers to each one. When you do this the DISAPPEAR from your passenger list. You will need to get more party members at the tavern if you want to fill up all your ships. DON'T sell the ship with the other 3 crewmembers still on it. You will lose anyone that is still on board.
2) The second way to do this is to capture a ship and do it when you assign a captain to the captured ship.
Make sure you have a high commerce skill. Then go to the tavern and find an officer that's for hire. Ask him how much he costs and he will tell you a lower price. Then say that's still too much. Then talk to him again and ask him how much he costs. He will now say the second price he offered. Tell him it's too much and he will lower it again. Keep doing this until it goes into the negatives. Basically, he will be giving you money for you to hire him.