Anyone interested in a pirate campaign should find a copy of Sid Meier's Pirates! that will play on a device that they own.
It's not only a lot of fun, but also generally pretty good historically, down to when and where wealthy ships were in the Caribbean on any given date.
One of the things that becomes clear very quickly is that you want to be a privateer, not a pirate, because otherwise, finding a place to make port becomes extremely difficult. And you want to make port regularly, because you'll need food and water, to repair your ship, to let your crew blow off steam and to get new recruits.
