gog.com or Xbox backwards compatibility?

I played the remake, which was pretty good, though now 20 years old itself.

tbh if you want to scratch the pirate-y itch, Assassin's Creed Black Flag is excellent, if just for the sea shanties.

Which has itself just had a remake released for it I see! I don't keep up with games these days.

"In a browser" is always an option:

https://archive.org/details/msdos_Sid_Meiers_Pirates_1987

https://archive.org/details/PiratesMacintosh

There are probably others, but Archive.org is misbehaving at the moment.

In a c64 emulator, full screen. You can find the .d64 floppy images online. Use a joystick or at least a cheap usb gamepad, the ship to ship fighting is more fun than.

Or if you have a real C64 with a CRT that would be best, but than with some kind of mass storage attached (anything that is faster than a 1541 since the game is so big it has to load before every fight or other activity).

The game can be pretty immersive and playing it through is a multiple hour endeavour.

If in a ship to ship fight, you gotta raise sails first (by moving the joystick up).

Edit: Vice is an emulator packaged in Debian Contrib, but you need the C64 ROM file (easy to find online).

The remake is on Steam

The Xbox remake from 2004 plays well on current-gen Xboxes.