The standard gameplay is Career mode in which the player tries to gain fortune, rank, lands, reputation and a wife by sailing around the Caribbean sea. The player rises to the top by trading, assaulting towns and ships, and taking on offers made by governors. The player can choose Expedition mode, in which the player chooses to command a famous expedition. An expedition is a much shorter game mode.
The game contains four nations and the player can choose which one to belong to.
The choice determines where the player will start, which ships he/she will have, the size of the ships crew, initial wealth and reputation. The choice will not require the player to support that nation during the game.
Historical time period
The player can choose which historical time period he/she want to start their career in. The time periods differ from each other in how favarable pirating is, which nation is strongest, and the nations navel fleet sizes. The "The Buccaneer Heroes" period is the most advantageous for piracy.
- The Silver Empire (1560)
- Merchants and Smugglers (1600)
- The New Colonists (1620)
- War for Profit (1640)
- The Buccaneer Heroes (1660)
- Pirates' Sunset (1680)
- Battle of San Juan de Ulua (John Hawkins, 1569)
- The Silver Train Ambush (Francis Drake, 1573)
- The Treasure Fleet (Piet Heym, 1628)
- The Sack of Maracaibo (L'Ollonais, 1666)
- The King's Pirate (Henry Morgan, 1671)
- The Last Expedition (Baron de Pointis, 1697)