Sid Meier's Pirates! is indeed a great game for hours of fun, however, gameplay gets repetitive and somewhat boring
Every single detail is where it has to be, the improving items, the tools, nothing is discarded, of course, there's always the small part of the role, like disguise and small hide-and-seek games in search for the "infidel", in fact, that's the only pointless feature in the game, if you are a pirate, shouldn't you be pillaging, killing, and raping more than helping the government? If pirates did that, they were not pirates, matey!
The fact is, Sid Meier's Pirates is a great game for hours of game-play on swashbuckler, an addicting game for everyone (yes indeed!), but the huge problem is that it gets repetitive and somewhat boring, the story never changes only the locations, you have to save your family, and you have to capture the same famous pirates flag ships and you have to snatch the same treasures, and to pillage the same towns, and to destroy the same villain hideout! Once you finish the game at the maximum level, and I mean getting married with a beautiful lady and all the game trinkets done, everything gets tedious and repetitive, its a must play for the ones who are crazy for piracy or the fans of the classic game, a game with more fun than any other great title, but a repetitive story and a weak motivation to keep playing the game even with all your objectives done.