This game is going sooooooooo well its ridiculous. I have converted my entire fleet to pinnace's and sloops, so they all move pretty quickly from port to port.
Furthermore, my pinnace flagship has 16 cannons on it, 60 gunners and 10 tons of gunpowder: it is devastating.
I've actually managed to 'take' two towns that I was never actually able to capture before simply by kidnapping citizens until the governor surrenders the town.
Previously, I always used my ship cannons to blow up the governors mansion, which usually had a very similar effect.
My fame score is currently at 5000+, and my infamy score at a nonexistant 0.
I have ships full of stolen booty and plenty of places to sell the goods. Life is good for this pirate