Pirates is a good game. That is if we look at where it is in comparison with current games. In comparison to the games that were around when this was released it was superb.
I am running it on win 8.1 with not problems whatsoever; OK, the graphics are dated, but not unplayably so; the sound is not the best around now, but again this is not a problem.
I loved the original game and this rework is just as good. There is dancing, which I was always crap at and I expect I will still be crap at; the fighting onboard ship takes a bit of getting used to; I expect that will come back to me, (Already lost and slung in a French prison, just because I attacked a French ship and got too close and started a boarding action when I really should have stayed away a bit longer!) The naval battle mechanics are pretty good, not Black Flag but this is a game that is 9 years old!
So, yes I do recommend it, I have had no problems getting it to run on 8.1, and it is a real reminder of the good old days! I got it in the winter sale, or perhaps that should be SAIL maybe? :-) and I have already abandoned one career in less than an hour. Not to self; always keep enough cash with you so when you escape from prison you can afford to repair your ship. (Attacking when your ship is damaged is not worth it, your victim can sail away!