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To enter the dungeon (tunnel next to the pirate town), you must first become the ruler of Tortuga.
To overcome the checkpoint, you need to talk to Thanatos, who is imprisoned in a chest in the southeast of the island (coordinates 63, 83). He will send you to a necromancer (black hut on the northern coast of the pirate island), and he will reward you with a Cloak of Darkness.
Then, follow the quest chain.
To overcome the checkpoint, you need to talk to Thanatos, who is imprisoned in a chest in the southeast of the island (coordinates 63, 83). He will send you to a necromancer (black hut on the northern coast of the pirate island), and he will reward you with a Cloak of Darkness.
Then, follow the quest chain.