The remaining ships and buccaneers set sail shortly afterward, planning to meet up on the island of Savona and make their decisions on where to attack from there. Several of the ships were delayed, and as provisions ran low and tempers ran high, Morgan decided to take the eight ships and 500 men he had and organize a raid on the Venezuelan port of Maracaibo. Upon their arrival, they found the Spaniards waiting for them in a fort defending the bay, but after a battle lasting less than a day, the Spaniards retreated. Morgan and his pirates tore down the fort and spiked the cannons by driving iron nails into the gunpowder touch hole, making it impossible to ignite the cannon, and thereby rendering it useless. After the destruction was over, they carried the fort's supply of gunpowder back to their ships.

The next morning, they set sail for Maracaibo, and found that once again the Spanish had fled, leaving the city mostly empty. The buccaneers searched the city to be sure no soldiers remained behind, then set up headquarters. Each day they sent out around 100 men whose job it was to round up prisoners and any treasure they could find. Any men they did imprison were tortured in an attempt to find out where the goods and other citizens were hidden. If a prisoner failed to reveal any pertinent information, he was put to death.

Onward to Gibraltar

After about three weeks of capturing and torturing prisoners and collecting their riches, the pirates decided to move on to the Venezuelan port of Gibraltar. They loaded their ships with their booty and their prisoners, and then set sail. They sent an advance party to command the people of Gibraltar to surrender to Captain Morgan, telling them that no quarter would be offered to any individuals who resisted. The ships arrived to heavy gunfire from the fort, but when the buccaneers landed and made their way on foot to the village, they found it deserted.

Alexandre Exquemelin wrote that “only a simpleton was left behind in the village,” further detailing how he was tortured and killed, as he could not give the pirates any specifics on where the city's wealth was hidden. Morgan and his men eventually captured a slave, and after promising him freedom, money, and a return to Jamaica, he led them to the Spaniards' hiding places. For several days they went where the slave led them, capturing prisoners and loading Spanish wealth on mules. When they had captured over 250 prisoners, they returned to the city.

Once back in Gibraltar, they interrogated and tortured the prisoners in order to find out where the citizens' wealth had been hidden. Once they'd gone through all their white prisoners, they questioned and tortured the slaves. One of the slaves promised to lead them to the hideout of the governor, and Morgan took 350 men and went in search of him. Bad weather and swollen rivers held them back, and although they returned to Gibraltar with many more prisoners, the governor was not among them. Another group, acting on the word of a different slave, did bring back a ship and four barques, complete with some, but not all, of the merchandise they'd originally carried. By this time, Morgan decided to leave Gibraltar and head back to Maracaibo with several prisoners who were to be ransomed back for 5,000 pesos. He and his men were anxious to get back to Jamaica, but in every port, there's a storm, and in this instance there was trouble ahead.

Fight or Flight

Upon returning to Maracaibo, Morgan learned that while he'd been in Gibraltar, the Spaniards had rebuilt and outfitted the fort at the mouth of the bay with artillery and soldiers, and that three Spanish warships had arrived and were blocking the only exit to the open seas. Morgan boldly sent men to the fort demanding ransom for the city of Maracaibo. The answer which came back from Admiral Don Alonzo de Campo y Espinosa was, “If you will surrender with humility all which you have taken, including all the slaves and other prisoners, I will have the clemency to let you pass and return to your own country.” If Morgan would not agree, the admiral promised he would “destroy you utterly, and put every man to the sword.”

With that threat, Morgan got busy. A captured Cuban merchant ship was disguised as a warship, and fitted with logs to simulate cannons. More logs were mounted on the deck, and painted and dressed to look like pirates. The ship was loaded with barrels of gunpowder that had been fitted with fuses. The merchant ship led Morgan's men on their attack, and it headed straight for the largest of the three Spanish warships. They sailed the vessel alongside it, fastened it to the warship with grappling hooks, and lit the fuses. The buccaneers onboard then escaped in small boats. The merchant ship quickly exploded and destroyed the Spanish warship. A second Spanish ship hurried away before it could catch fire, but hit a sandbank and ran aground. Amid the chaos, Morgan's ships captured the third Spanish vessel.

At that point, only the heavily armored fort stood between Morgan's men and their freedom, and Morgan again used a brilliant ploy to trick the Spanish. This time, he sent boats loaded with men to the shore, to make the Spaniards believe a land attack was coming. However, they returned with the men still onboard, most hiding in the bottom of the boats. In the meantime, the Spanish moved their guns to cover the land approaches to the fort, and in the darkness of late night, Morgan's ships quietly rode the tide out of the harbor. They were not spotted by the Spanish until they were out of range, and Morgan once again returned home to Port Royal in triumph.