A game of Libertalia takes place over three voyages (or “rounds”). Each voyage begins with players gaining an identical set of 6 character cards. Every day during the voyage, players simultaneously select 1 character from their hand to play. Those characters are placed on the island from lowest to highest rank (player reputation breaks ties). Players will activate daytime abilities on those characters in ascending order, then dusk abilities and loot selection in descending order, with characters entering each player’s ship. Lastly, night abilities on characters in ships activate.

At the end of the voyage, players will activate any anchor abilities on characters and score their loot tokens and doubloons. They will then discard those characters, loot tokens, and doubloons, keeping only their hands of characters that were not played. At the end of the third voyage, players reveal their final scores to determine who history will remember as the wealthiest pirate.