I keep coming back to this one.

Took me a while to get into it but it's kinda like Mount and Blade with ships, and with considerably more shallow combat.

I like Sid Meier games, specially Sim Golf. His games have a way of covering the topic fully in the simplest possible way.
In this game the fighting is extremely simple, but it's all you need to feel as if you are fighting.
The dancing mini-game seems silly at first but once you get used to it you actually feel as if you are dancing.
This game has so much to offer and in some ways it seems like wasted potential, but it's actually just very economical.
For example, there is a hidden turn based strategy game ala Civ in the Land Battle minigame.
another example, every city has a fully 3D environment you can walk around, but only in the extremely rare case that you are sneaking through it.

1 game took me about 2 days to finish on easy mode (working up to medium while playing)

I'm now playing on Swashbuckler, the hardest difficulty. I started on the middle difficulty and notched it up as I played the campaign. The game gives you the option to do so whenever you divide the plunder successfully.
Even though the difficulty is high I'm playing much much better than my first playthrough.
Pirates! allows for a lot or versatility in terms of how you complete the game

I decided to boot up this game again after not playing it for years. Immediately lost 6 hours to it. It's insane how well it runs, considering the game is nearly 20 years old now. This is by far still the most fun pirate game ever made, with a level of depth that the majority of modern triple A games simply do not have.

This is a phenomenal game that brings you back to your childhood of when people were passionate about the games they made, actually finished them, and they were actually fun.

Even though this game is old, it is still one of the best Pirate game of all time. I highly encourage anyone who likes Pirates to play this game. Will play again.

I used to play this as a kid, it's fun nostalgia

one of my favorite childhood games of all time and the main reason why I know the name Sid Meiers. This was an easy purchase. Hell, it still works today too!

If you have never played this game, and you love pirates you're doing yourself a disservice.

10/10 yo ho yo ho a pirates life for me.

i played this game a ton as a child but was never able to beat it, now im a professional game designer and the fencing is so ♥♥♥♥♥♥♥ frustrating lol but it's so fun pirating, i will always enjoy pirating too much to get bogged down in repetitive systems. dead by daylight is a QTE simulation so this is infinitely more enjoyable ad nauseum than that

Grew up on this game. It's still good.

One of the all time great PC games, and still worth playing even today.

Nostalgia meets quality. This game is one I used to play for hours as a child, and all these years later it still holds up. Despite the gameplay loop being a little repetitive, it constantly feels fresh and rewarding because the control schemes and tactical elements are done so well. The ability to dynamically adjust the difficulty and rewards on the fly is also a great addition. This game gives you the freedom to make your own destiny. Side with any given nation and build your legacy, or scorn them all and become infamous and hunted. As with most Sid Meier games, the path you take is nearly limitless. You can roll with one boat and a slim crew, or fill out a fleet with an army of pirates. You can search for treasure, attack ships, capture townships, and so much more. It really feels very liberating. The graphics even have their own charm and still hold up to this day. Truly a timeless game.