The most vicious pirates of the Carribean want to find out who is the biggest cutthroat, so they make a bet. They're all sailing the same route, and whoever can show the biggest amount of loot at the end of the journey wins. Master pirate Redhook plays the judge, but there aren't many rules - everything is allowed as long as it earns gold.
is one of these boardgames on the computer. The Carribean becomes a playfield, sailing is a matter of rolling the dice and then moving along a predefined line. The square you land on this way contains an event. This can either be something simple like 'go two steps backwards', 'you find 500 pieces of gold' or a multiple choice question. The questions test your knowledge about historical pirates, pirate novels, pirate movies and general sailing-related stuff. Correct answers are rewarded with gold and additional supplies.
Supplies like a compass or cloth can be used to avoid negative effects of events. The compass, for example, helps you navigate through thick fog. Without one, you have to pass one turn. You can also keep hostages in your cargo hold, in the hope to receive ransom for them later. Cannons are perhaps the most important piece of equipment for every pirate, though.
The reason is obvious: The competitors' ships can meet on the same square. Then, a battle between them ensues. For each cannon on board, the pirates can roll one die and whoever rolls the higher numbers wins, looting some money from the enemy and 'winning' the square. So, the more cannons, the bigger the chances of success. Pillaging cities is done the same way: If your ship lands on the right square belonging to one, you can attack the fortress in the hope to sail away with the town's riches.
Being a 'digital boardgame',of course suffers from the same problems as the whole genre. First of all, the trivia questions are repeating themselves too quickly. Once you know them, a good part of the motivation is gone. Second, the more humans participate, the more fun. Playing against AI enemies is alright, but it can hardly compare to the Schadenfreude (sorry, there's no aequivalent translation of that word - look it up) you feel if you've just beaten someone sitting next to you in a battle and stolen his or her money. In any case, it's the perfect party game.
ImagiSOFT started offering the full version of this Shareware game for free in 2004. It can be downloaded from their website (see related links), but that doesn't mean it has gone into public domain. Free redistribution still isn't permitted - and that is why there isn't a direct download link right here on this site. Anyway, it should be worth the two additional clicks needed to head over there.