Caribbean Legend - Pirate RPG - A Good Pirate Game 

Long-time Sea Dogs player here. Caribbean Legend is the amalgation of years upon years of autistic modding and development on the back of the Sea Dogs franchise, and it is fully in the spirit of what a game should be. It challenges you, there's an element of RNG, it's unforgiving and you can't pay your way out of a challenge with a credit card. It's a labour of love, and despite its very dated graphics, it is what games should aspire to be. As a new player it will be insanely difficult and it's a game that should be replayed at least once after finishing it. I'd give the game 10 Ritalin pills out of 10 therapy sessions, highly recommend!

I totally agree with you about Sid Meier's Pirates. I played many hours on that game.

The music is so cheerful, I love it

There is an insane ship you can steal off the Spanish in one of the story missions early on that has some of the best cannons in the game. We're talking grape shot taking 90% of a crew off a ship at long ranges.