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Caribbean Pirates Trivia Quiz

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The rise of piracy

Caribbean sea piracy had its heyday in the late seventeenth and early eighteenth centuries. Which of the following contributed most to its rise?


Skull and crossbones

The “skull and crossbones” flag was often used by pirates in real life, and nearly always used by pirates in fiction. What was the flag’s special nickname?

Henry Morgan (1635-1688)

One of the most famous Caribbean buccaneers was Henry Morgan. After years of swashbuckling on both sides of the law, what was his occupation in middle age?


Blackbeard (?-1718)

Blackbeard (Edward Teach) was a giant of a man with a mane of black hair and — his trademark — a luxuriant black beard. What did Blackbeard do as a special ploy to make himself more fearsome in battle?

Maiden voyages

Two of the most famous female pirates were Anne Bonny and Mary Read. Both sailed with “Calico Jack” Rackham. When they were condemned with Rackham in Jamaica in 1720, how did the two women escape hanging?

Dread pirate

In the film The Princess Bride, there is much discussion of “the dread pirate Roberts”. Such a pirate existed in real life. What was his first name?


Woodes Rogers (1679-1732)

Starting in 1708, a former merchant named Woodes Rogers made a fortune harrying Spanish shipping under a “letter of marque”. He then switched to a different line of work. What was it?

Silver bird

Like many pirates in fiction, Long John Silver in Robert Louis Stevenson’s novel Treasure Island keeps a parrot. What is the parrot’s name?

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