Reach the rank of Count with any or all nations. Then, go into ship battles with any desired ship. Damage it a lot, but not to the point where it explodes. Keep the ship and go to a port where you are at the rank of Count or higher. Talk to the shipwright. You will get free repairs. You can repair a damaged ship for free and sell it for a lot more.

When the Governor's daughter gives you the hand signal, select the button for the hand movement immediately after she gives you the signal. You will do a special dancing move which will get her heart up very fast, if you do it many times in a row. If her heart is big enough when the mini game is over, instead of kissing her hand, you will spin her around and she will then kiss you. Afterwards she will likely give you a present or extremely valuable information.

Attacking and boarding a smuggler's vessel usually yields a specialist (for example, Carpenter, Sailmaker, etc.)

When battling other ships, get in front of them. Have them chase you, and when your guns are fully loaded, turn, fire, and straighten again. Repeat this until you wish to board or their sail falls and they surrender. It is best done when you use grape shot or chain shot.