re: Sid Meier's Pirates

start quick and fast ships like other said. build your fleet and don't forget to buy cargo where it's priced low and sell at better price at other ports. Use the letters of marque don't go full on pirate at first. Once you get a good sized crew/fleet try to find a treasure fleet to attack. Also don't be afraid to attack towns and loot. Mary a a gov daughter. Don't overstay your welcome retire before it starts falling apart.

I loved that game on the C64. I played so many hours on it.
Another think I miss was the book that came with it. It was very interesting, and got me to look up more stuff about pirates.