The Gunpowder Plot

This quest unlocks after completing the "We Demand A Parley" quest. To start it, return to the tavern in Nassau and talk to Vane.

1. Follow Vane

Simply follow Vane until you reach the roof of a house overlooking the cave entrance. After a brief discussion about what to do, Vane will head off to carry out his part of the mission.

2. Mark the kegs in the cave

Go over the top toward the cave entrance and kill the guard guarding it - for example, by hanging him.

The cave is small and filled with a few patches of tall grass. It is guarded by five soldiers. Once you enter the cave, one soldier will move deeper inside, while another may - or may not - start patrolling the area in a circle.

Depending on how the situation plays out, eliminate all the soldiers, preferably by luring them into the tall grass and using assassinate. Once everyone is dead, mark both barrels.

3. Mark the kegs at the camp

Exit the cave through the second entrance. There is a soldier standing at the exit with his back turned to you, so assassinate him.

After stepping out into the open space, you should notice a small hill ahead of you, thickly overgrown with grass, and a tent with three soldiers standing next to it. The first barrel is right beside the tent. You can, of course, start by taking out the soldiers guarding it, but there is a chance that two soldiers standing a bit further away will spot you.

Therefore, head further ahead first, to the other side of the hill where you will find the second tent and a gunpowder keg guarded by four soldiers. Wait for two of the soldiers to finish talking - and for one of them to start patrolling in a circle - then discreetly take them out one by one, moving clockwise. Mark the barrel and return to the first tent.

Keep your distance so you lure only one soldier toward you, then whistle. Assassinate him, and then get rid of the two soldiers standing near the tent. Once you mark the barrel, this quest will end and the next one will unlock - Commodore Eighty-Sixed.