I played first edition back in the very early oughts, and I did not enjoy it much. To be fair, the game group I played with didn't click with me, so it may not entirely be the game's fault, but here are my beefs with it:
It's a pirate game that completely ignores the preconditions for piracy: seafaring trade, a surplus of desperate seafarers, and weak law enforcement. Snapped my suspenders of disbelief a bit. It does rather avoid this by, as having been mentioned, set most action on the mainland.
It keeps secrets from the players. The worst example (spoiler)
In a lot of ways, it feels like the last gasp of meta-plot driven '90s game design. 2nd edition may have changed this, but I haven't cared to find out.
The game mechanics IIRC were cute and somewhat interesting, but not enough to stick in my mind after twenty years...
In short, I can't recommend it based on my limited, and dated experience. If I were doing a "fantasy pirate swashbuckling game", I would Start With Earth and just run with the historical Caribbean and go wild with it. System wise I would almost certainly use GURPS, but Savage Worlds also does a dandy job for swashbuckling action.