Silver for Cartagena

How to get this quest (top)

If you have a Letter of Marque from any nation, or if you have joined the Pirate Brotherhood at Nevis, you can earn promotions. At high enough rank, governors will introduce you to their relatives. You can marry a relative or you can overwhelm them with charm. Either way, if you then continue to talk to them, they may tell you about the Spanish silver train on its way to Cartagena.
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If you are a pirate, are at least level 12, have no Letters of Marque and have not joined the Pirate Brotherhood, then Meredith Byrom will appear in the tavern at Smugglers' Lair on Camahogne/Concepcion/La Grenade/Grenada (the island's name depends on the period). He will tell you about the Spanish silver train on its way to Cartagena, provided you agree to hire him as an officer.
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Cartagena (top)

Sail to Cartagena. Go to a tavern. In the tavern nearest the port are some Spanish soldiers. For the price of a couple of gold coins for a drink, any one of them will tell you that he's from a fleet waiting for a cargo to arrive, and that his officer is in the other tavern.

You don't need to go to the first tavern but you do need to go to the second tavern, in the town centre. A Spanish officer is there at a table, and a soldier is standing around. You can join him for a drink and ask about the Spanish silver train. He tells the soldier to go and invite his squad to join in. Then you'll have to fight the squad, either inside or outside the tavern.

Or you can talk to the bartender about the Spanish silver train. He tells you to be quiet and warns you about the officer.

In any case, the waitress Jimena López will talk to you. Buy a bottle of wine from the bartender. This sends you upstairs, where Jimena will join you.

The Deal (top)

Jimena López wants to send medicine to a local Indian village which is suffering from disease. She offers to set up a deal; you'll bring 100 units of medicine for the Indians and they'll help you to ambush the Spanish silver train. If you don't happen to have 100 units of medicine already, you will need to buy it. Medicine is an import in Cartagena, therefore expensive; you may want to sail to Aruba or Curacao, where it's an export and therefore cheaper. When you have the medicine, return to Cartagena, speak to Jimena again and mention a blue dress. Rent a room, then Jimena will join you to confirm that you have the medicine. Wait two days - you don't have to wait in the tavern, you can do other things such as repair your ship or get swords polished by the blacksmith.

Meet the Indians (top)

Two days after talking to Jimena, sail to Dolphin Sands, the beach to the west of Cartagena port. A group of Indians are on the beach but only one of them will talk to you. You can unload the medicine right away or you can demand that the Indian leads you to the Spanish silver train before you unload it.
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The Indian will now lead you into the jungle. Follow him as he walks to the exit of each location. In a swamp, you suddenly collapse.
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In the Village (top)

You wake up in the Indian village. An Indian tells you that you were bitten by a snake. By combining the medicine you brought with his own stuff, he can cure you. If you chose to keep the medicine until after the attack on The Silver Train, you send an officer or crewman to get it now.
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After you are healed, an Indian will lead you back out into the jungle - and back through the swamp, where you will not be bitten by another snake! Follow the Indian to another jungle location, where he leaves you.
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The Silver Train (top)

A short time after the Indian has left, you spot the advance guard of the Spanish silver train approaching from the right. Talk to an officer if you have one, or to yourself. Shortly after that, the main force arrives.

You are hidden from the main track, and from the Spanish silver train's guards, by some trees. This allows you to shoot first, unless you approach too close and they spot you.

Kill all the soldiers. QB update. Talk to an officer if you have one, or to yourself.

Teleport to the next jungle location. Observe a group of Spanish soldiers heading towards you. Fight them.
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Return to the Ship (top)

Find your own way back to the beach. QB update. Observe a Spanish ship out at sea. Receive 300 units of silver (or as much as your fleet can carry, if less than 300).

At sea, you will fight at least one ship of the Spanish fleet. The rest starts out near Cartagena and heads towards you. And the fort is alerted to you. Try to fight your way out as best you can!

If you weren't previously hostile to Spain, you are now. The fort will remember your ship. If you ever want to visit Cartagena again, you must either stay clear of the fort and land at Dolphin Sands, or be in a different ship that the fort does not recognise, or pay a Spanish governor to make peace.