Easiest Way To Get Ships
The easiest way to capture a ship in battle, is to run it into land. This can be done by luring the ship so that it chases you and right before you hit the land make a sharp 90 degree turn. The enemy ship will then ram itself into the land. After that it will say that you win the battle.
Keep the Crew Happy
Sailors are happiest when their share of the loot is more than a pittance. Therefore, before divvying the spoils, sacrifice part of your crew in battle. This will significantly increase each man's share.
(Note: Don't slaughter all of your men or you may find yourself captured.)
Seize control of Seafaring Vessels
The easiest way to seize control of a seafaring vessel (particularly when you are out-gunned and out-manned) is to climb aboard and fight the captain on her deck.
Women and Marriage
Use your charm and charisma to win over the favor of townswomen. When you visit the town again, they will freely give you information that is otherwise hard to come by. Be content to just “Make Conversation” with perspective brides until you have gained considerable rank and reputation. Then marry into the governor's family.