Pirate Lore: So, You Want to Be a Pirate?

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By Evelyn Kelly, PhD 

Ahoy, pirate fans! How much do you really know about real pirates? Watching “Pirates of the Caribbean” is fun—but let’s dig deeper into true pirate history. 

Related: How to Watch all “Pirates of the Caribbean” films in chronological order

Women Pirates? Aye! 

pirates of the caribbean poster

Think pirates were only men? Meet Anne Bonny, a fierce Irish woman with a dramatic life. The illegitimate daughter of a lawyer, Anne was raised disguised as a boy named Andy. After marrying a poor sailor, James Bonny, she was disowned by her father—and allegedly set fire to his plantation in revenge. Anne and James moved to Nassau, a pirate haven, where she met Calico Jack. Disguised as a man, she joined his crew and fought alongside him until their capture. Her final fate remains a mystery.

Related: How to Watch all “Pirates of the Caribbean” films in chronological order

Privateer or Pirate? 

Privateers were legal pirates, hired by governments to attack enemy ships. Pirates, on the other hand, plundered for personal gain. The line was thin, but the consequences were real. 

Pirate Fever! 

Today, pirate fever lives on—from Halloween costumes to museums. We visited several and highly recommend: 

Famous Pirates and Places 

  • Henry Morgan: A Welsh privateer turned pirate, he attacked Spanish ships and burned old Panama in 1671. Knighted by the British, he became both feared and celebrated.
  • Blackbeard (Edward Teach): Famous for his long black beard tied with ribbons, he blockaded Charleston in 1718, demanding medicine. He later retreated to North Carolina and was captured that same year.
  • Captain William Kidd: Hired by the British to attack enemy ships, he went rogue and was hanged in 1701. Legend says his treasure still lies hidden in the Caribbean. 
  • Tortuga Island: Once home to meat sellers or “boucaniers” who turned to piracy when they found it more profitable. We recently visited this windy, rugged island, imagining the early buccaneers smoking meat before taking to the sea.
  • Barbary Corsairs (North Africa): Pirates based in Tunis, Tripoli, and Algiers terrorized the Mediterranean. President Jefferson sent the U.S. Navy and Marines to stop them, leading to the “shores of Tripoli” line in the Marine Hymn.
  • Castillo del Morro (Puerto Rico): This Spanish fort in San Juan was a constant target for British pirates like Sir Francis Drake—but it was never taken.
  • Caribbean Islands: Many islands, such as Bonaire, still show the impact of pirate raids, with towns once built inland for safety. 
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How to Dress Like a Pirate 

Want to join the fun? Start with a white shirt, leather pants or a big red skirt, and a bold belt. Add a bandana, headscarf, boots, and flashy jewelry. Eye patches and fake tattoos complete the look—bonus points for a stuffed parrot on your shoulder! 

Related: Armchair Adventures: Beautiful Savannah

Smart Tip 
If you’re cruising the Caribbean, take island excursions to explore pirate lore firsthand. It makes your Pirate Party so much more authentic!