The Real Pirates of the Caribbean

Contributor: Suzanne Riordan. Lesson ID: 13055

Pirates make great movie characters, but real pirates make great history! Learn about a sunken pirate city, one pirate honored as a hero and one killed as a criminal-the real pirates of the Caribbean!


World, World

learning style
Auditory, Visual
personality style
Beaver, Golden Retriever
Grade Level
Middle School (6-8)
Lesson Type
Dig Deeper

Lesson Plan - Get It!

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  • Do you know there is part of a sunken city on the bottom of Kingston Harbor in Jamaica?
  • And did you know it was a famous "pirate city"?

It was filled with rough-and-tough pirates who plundered Spanish ships, sold their goods to English merchants, and spent their fortunes on drinking and wild living. It's said that a pirate might spend as much as 3000 "pieces of eight" in one day in Port Royal ("Pieces of eight" were Spanish silver dollars). It would take a local man several years to earn as much as a pirate would spend in one day!


With all that money coming in, Port Royal grew to be the richest and largest city of the Caribbean at the time, and one of the largest in the world. It was the "home base" of many of the pirates of the Caribbean.

  • But how did it end up sinking into the sea?

During the Golden Age of Pirates, many pirates found the islands of the Caribbean to be a great place to gather (and spend) their riches.

In a previous Related Lesson, found in the right-hand sidebar, you learned that many pirates of the Caribbean were men who had settled on the island of Hispaniola (now Haiti and the Dominican Republic). In this lesson, you'll learn about two famous pirates of the Caribbean, and one famous Caribbean pirate city.

When the Spanish drove the buccaneers out of Hispaniola by killing the wild boars that they hunted, they settled on the island of Tortuga, north of Haiti, and turned to piracy. The Caribbean was a great place to be a pirate because there are so many little islands like Tortuga to hide on.

Map of the Caribbean

Many of the natives of these islands had died from diseases brought over by the Spanish, so the pirates could go almost anywhere they wanted without fear of being captured. Also, there were large market towns, such as Nassau (in the Bahamas) and Port Royal, Jamaica, where the pirates could sell their booty for cash.

The English took Jamaica from Spain in 1665, and the English governors gave the French pirates letters of marque to attack Spanish ships in the area. The French governor of Tortuga gave the English pirates letters also, so an all-out attack on Spanish ships began. Port Royal became the unofficial capital of Jamaica and the center of pirate activity. To learn more about "letters of marque," go to the first Related Lesson in this Pirates series, found in the right-hand sidebar.

You've already been introduced to some pirates of the Caribbean. You learned about Blackbeard, "Black Bart" Roberts, and Captain Kidd, in a previous Related Lesson. In this lesson, you'll get to know some other Caribbean pirates: Henry Morgan and "Calico" Jack Rackham.

Henry Morgan

Henry Morgan

Morgan was probably the most famous pirate who made Port Royal, Jamaica, his home base.

Henry Morgan was born in Wales. Not much is known of his early life, but historians think he may have joined a privateer vessel heading to the New World. However it happened, he somehow ended up in the Caribbean and joined the English fleet, and participated in many raids against Spanish ships and colonies. He was then given command of his own ship, and soon rose to command the whole fleet. He was given letters of marque to attack Spanish ships but became more famous for his land attacks than any attack at sea.

Morgan's fleet attacked the Spanish in Cuba and easily defeated them. But they did not gain much treasure from this attack, and many of his men were disappointed and left. Knowing he had to bring in more loot to keep a crew of privateers and buccaneers motivated, Morgan then decided to attack Porto Bello, Panama, where the Spanish stored much of their wealth. Morgan came up with a clever plan. He would anchor his ships far away from the city and use canoes to transport his men. They were able to capture all three of the forts and carry back to Port Royal around 100,000 dollars worth of money and loot.

He next planned an attack on Maracaibo and Gibraltar, in what is now Venezuela. These cities lie on a large lake in northern South America.

map of Venezuela

Both cities were easily taken, because most of the people left when they heard the English were coming. There are reports that Morgan's crew tortured some of the remaining citizens to get them to reveal where any hidden riches were.

But the Spanish would not allow Morgan to escape with their booty. They brought in an armada of Spanish ships to face him and force him to surrender the goods. Morgan and his men discussed their options. They refused to surrender and came up with a plan to use a "fire ship" against the Spanish fleet. A fire ship is a ship that is filled with combustible materials, set on fire, and steered into an opposing fleet to hopefully catch their ships on fire and cause confusion and chaos. Morgan's crew used hats and wigs on wooden poles to make it look like a crew and fitted out the ship to look like it was heavily armed with cannons.

Henry Morgan Destroys the Spanish Fleet at Lake Maracaibo

Image by Alexandre-Olivier Oexmelin, via Wikimedia Commons, is in the public domain.

The plan worked, and Morgan and his fleet returned to Port Royal with all their loot. Morgan used his money to buy a plantation.

Soon, the Spanish began plundering English ships, and Morgan was called into action again. He was given permission to carry out any attack he considered necessary to preserve the peace of Jamaica. He now had the largest army of privateers in the Caribbean, and he decided to attack Panama. Morgan's fleet of 30 ships and 1200 buccaneers was able to take the Spanish fort, and they endured a long, difficult march through the jungle to capture Panama City and defeat a much larger Spanish force.

What Morgan did not know was that while he was in Panama, England and Spain had signed a peace treaty. That meant that Morgan's raid on Panama occurred after the treaty was signed. As you can imagine, the Spanish were very upset about this; so, to avoid another war, the English decided to arrest Morgan and send him back to England. Fortunately for Morgan, he was considered a hero in England and was therefore never actually charged with any crime. He returned to Jamaica, served as governor there, and lived there until he died.

Morgan was considered a hero to the English, who saw him as an unofficial naval officer who defended the British colony of Jamaica from the Spanish.

  • How do you think the Spanish saw him?
  • What is your opinion of his actions?

"Calico Jack" Rackham

John Rackham is a famous pirate of the Caribbean for several reasons. He designed the popular Jolly Roger flag of the skull with crossed swords or bones underneath. And he had not one, but two, female pirate crew members: Anne Bonny and Mary Read, whom you'll learn about in our next Related Lesson. This was very unusual. He also had that memorable nickname:

  • "Calico" for the kind of fabric he wore — that is, a simple, unfinished cotton
  • "Jack," as a common nickname for "John"

Calico Jack was born in or around 1682 to English parents in Jamaica and began a seafaring career on a privateer ship that worked the New York coast. The crew members became upset with the captain, who ran from French ships rather than facing them. Rackham brought the crew together to vote on the captain's actions, and they decided he was a coward and should be replaced. They sent him off with some of his supporters in his own little sloop, and Calico Jack became captain. This is called a "mutiny" — a rebellion against authority, and it happened fairly often on pirate ships!

Calico Jack took his ship south to the Caribbean, attacking all merchant ships he encountered on the way. He liked to attack smaller vessels sailing near the coast.

Calico Jack did capture a larger vessel called the Kingston, but this got him in trouble. The merchants of Port Royal had seen the capture and paid a crew to go out and re-capture it. Calico Jack tried to get away by taking the ship to Cuba, but the pirate hunters found it at anchor there and stole it back. Calico Jack and his men hid in the woods, so they were not captured, and they ended up stealing a small sloop from the Spanish, who had stolen it from the English.

Calico Jack and his crew decided to sail back to Nassau (in the Bahamas) and ask the governor there for a pardon, so they could be "legal" privateers instead of pirates. They were granted the pardon and were allowed to stay, but they were not given letters of marque to become privateers. So, they continued on as pirates, terrorizing all the small vessels they encountered. Around this time, Calico Jack met Anne Bonny, who had some experience with piracy, and he took her on as part of his crew. He later took on Mary Read.

One day, Calico Jack met some English pirates aboard their vessel at anchor in Jamaica and invited them to come and have a few drinks with him and his crew. They all got drunk and were attacked by pirate hunters, captured, tried, convicted, and sentenced to be hanged. Calico Jack was executed in Port Royal in 1720. His body was covered with tar and hung in a cage at the entrance to the city as a warning to pirates.

End of the Golden Age of Pirates

The Golden Age of Pirates was coming to an end, and so was the "pirate city."

As you learned in the opening, Port Royal was eventually destroyed by an earthquake, and part of it sank below the water. On the day of the earthquake, the dirt under a large part of the city slid into the harbor, and tsunami waves washed over what was left. 2000 of the city's estimated 6500 residents died. Many died later due to the effects of the disaster. Another reminder that crime doesn't pay!

Watch The Riches of Jamaica's Port Royal, from National Geographic, to learn more about it:

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The images below show how the landscape of the city changed.

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After this disaster, many people turned against the pirates and began to urge the government to make laws against piracy. They felt it was a punishment from God for the wickedness of the city. The "Pirates of the Caribbean," along with their "Pirate City," began to fade into history.

Now, head over to the Got It? section, where you'll write a newspaper article about the disaster and study the geography of the Caribbean!

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