Ravage the high seas, loot, pillage, plunder and attempt to conquer all you see or just burn it asunder. Yar!
I finally found the game through gamespot's buy it - listed under gogamer.com.
Supposidly this game was released in September of 1999, but I never found it during that time period. I finally found it on 11/11/05. The full version is far superior to the demo. The gameplay itself is realistic to the times histortically. The game play varies from 1625 to 1700. The diffculty increases depending on the time period and hence the technological advances (which makes perfect sense). Depending on the time period determines where your adverture will begin. You play the role of a pirate captain. Your actions influence the life of you, your crew and life in the Caribbean.
You are given a large variety of choices for your actions. You can use diplomacy, torture, naval raids, or land raids by pillaging or conquering a town. Towns require strategy and numbers to overcome so be sure to manage your men and your supplies wisely.
The game play itself has average graphics by today's standard, but for 1999 they aren't half bad. Cutthroats has some amazing still frame shots. The idea of crewman loyalty is highly prized in the game. Also the idea of smaller colonies can easily be bullied by threatening the town (by visiting the govenor). Your boat may "randomly sink" during a city seige, but the cause of this "randomness" is either the city bombing your boat through cannon fire and with your attention on the land forces, you do not see the attack on your boat (until your officer informs you of the danger). Your ground forces require micromanagement because pirates aren't too self modivated. Other than that the game play is easy going.
Swelling your ranks can involve city recruitment or sea impressment. Either way, you always want extra sailors in order to secure enemy ships and increase your naval power. Good luck in your pillaging.