Cutthroats: Terror on the High Seas (PC, 1999) for sale online

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Cutthroats: Terror on the High Seas is a strategy game where players take the helm of a pirate ship and terrorize those who cross its path, whether on land or at sea. Players can choose to sink ships or capture them, kill enemies or kidnap them, raid towns or look for work within them. The setting for Cutthroats is the Caribbean Sea region during the 17th century. It is the golden age of piracy and a pirate ship will become entangled with merchants, soldiers, rival pirates and other parties to engage. The game's real-time strategy engine allows players to fight simultaneous battles on land and sea. The men in the boats blast ships entering the harbor while other members of the crew sack the town and beat up the landlubbers. Cutthroats features six million miles of ocean waters, 70 ports and towns and hundreds of ships to attack or avoid. Although piracy is an option in Cutthroats, players can also choose to seek a Letter of Marquee and fight for the crown as a privateer. No matter which option a player chooses, a good captain will remember to keep his or her crew supplied with plenty of gold and rum. Otherwise, the player should expect a mutiny and a long walk off a short plank. Players who amass enough wealth and escape enemy swords can retire as nobility. Those who fail wind up penniless, dead or in prison.