Sometimes Hollywood writers have their work cut out for them, having to concoct stories of action and adventure that will capture our imagination. Sometimes, though, truth is stranger than fiction.

The world of piracy and some of the characters in it seem to come from the movies or adventure novels instead of historical documents. But, these people really did exist and some of their exploits are so unbelievable that you’d swear it isn’t true.

Well, they are and they’re fantastic! We’ve combed the history books and found a few familiar names that you’ll enjoy learning more about, and more than a few names that you’ll be surprised to hear about for the first time.

 

Here are some of those characters.

The Barbarossa Brothers

Barba Rossa – meaning Red Beard in Italian – Aruj and Hizir built their fortunes by capturing and plundering ships in the Mediterranean. By 1516 the bothers were assigned control over the entire Barbary coast by the Ottoman sultan. The brothers became so fearsome that their Christian enemies formed a fleet known as The Holy League specifically to defeat them.

 

Sir Francis Drake

This Englishman is most famous for being the first captain to circumnavigate the globe. However, throughout his career he was licensed by Queen Elizabeth I to rob from the Spanish. He amassed quite a fortune, was enthusiastically Knighted, and later played a significant role in defeating the Spanish Armada.

L’Olonnais

This is perhaps the individual that caused pirates to have such a vicious reputation. In the mid-to-late 1600s it was documented that he would hack his Spanish victims to bits, tie ropes around their necks until their eyes bulged out, and was even once rumoured to have cut out the heart of his enemy and took a bite. Karma eventually got the better of him. He was captured by a tribe of cannibals in 1668 and never heard from again.

Sir Henry Morgan

This famous pirate sounds like he could have inspired a few of today’s politicians. After a series of violent attacks across Panama, Cuba, and Venezuela – using priests and woman as human shields – Henry Morgan eventually moved on to become the acting Governor of Jamaica between 1678 and 1682 passing anti-piracy legislature and actively prosecuting pirates.

And Yes. This is THE Captain Morgan

Captain Kidd

Captain Kidd’s story is short lived. Beginning his career as a pirate hunter in 1696 in the Indian Ocean, Kidd quickly turned to the dark side and became a pirate himself. This flip flop left him with very few allies, and the British East India Company quickly capture him and left his executed body on display of the River Thames as a warning to other pirates. He was, however, able to make a quick stop in New York’s Gardiner Island to bury treasure before his capture. Maybe it’s still out there somewhere.

Calico Jack , Anne Bonny & Mary Read

This story feels like it was tailor made for Hollywood involving not only John Rackam (Calico’s common name) but 2 infamous female pirates.

Mary Read had already made a name for herself at sea, so to speak. She was actually disguised as a man while she looted the Caribbean before joining Calico’s band or drunken pirates.

Not much is known about Anne Bonny except that she left her husband to be with Calico. Legend says that she was not fond of playing into the day’s gender roles, and would promptly stab a man in the gut for even insinuating that she didn’t belong above deck. Bonny and Calico plundered many ships, which is how they met Mary Read.

Eventually the group was overtaken by Jamaican forces in 1720. While the men hid in their cabins, the two women pirates fought tooth and nail. They weren’t successful, but they were the only 2 of the party to survive. The Jamaicans took pity on the women, as they were both found to be pregnant.

 

Charles Vane

Vane gained a reputation for cruelty as he raided English and French ships throughout the Bahamas.

Vane’s story is most notably as leader of the pirate rebellion including other Nassau pirates like Charles Yeates, Calico John Cockram, and Blackbeard. King George I extended an offer to pardon all pirates who wished to abandon the lifestyle. While many pirates took up the offer, Vane lead the charge for those who wanted to continue on as they are and managed several narrow escapes from the law and rival pirates while doing so.

Black Bart Roberts

Black Bart’s first act as official pirate Commander was to seek revenge for the death of the commander that came before him. Landing on his enemy’s Portuguese island in the dead of night, his group killed a significant percentage of the male population and made off with as much treasure as the men could carry. Soon after they overtook a Dutch ship followed by a British ship. This string of success resulted in Roberts’ reputation as being “pistol proof”.

Black Bart took his luck further by collecting a massive bounty of gold and jewels meant for the King of Portugal, but that’s where the luck stopped. His shipmate made off with the booty, and was shortly after attacked by a team of Barbados pirate hunters killing most of his mean and greatly damaging his sloop.

The tide’s turned again, and Roberts enjoyed a large string of successful attacks in Newfoundland, Brazil, West Africa, and throughout the Caribbean from 1719 to 1722.

His death came from a grapeshot to the throat after which he was buried at as as per his wishes. The news came as a shock to both the pirate community and Royal Navy. Both thought of him as invincible, and many viewed him as a hero.

 

Edward Low

Low burned the majority of the ships he captured, more than 100 throughout his short 3-year career as a pirate.

Hi claim to fame is, you guessed it, violence. But this was not your average pirate assaults. Low’s attacks were so obscene that Arthur Conan Doyle described the pirate as a  “savage and desperate,” and a man of “amazing and grotesque brutality”

 

Black Sam Bellamy

Black Sam’s reputation is the opposite of the majority of other pirates mentioned so far. Although his career as a pirate involved serving under Black Beard for a time, and capturing many ships, he was known as a gentleman. He was a tall and dashing figure, always well dressed, and ran his crew like a proper democracy. His men were so fond of him that they often referred to Black Sam as the “Robin Hood of the Sea”.

His good manner was also extended to his enemies. His largest fortune came about when he captured a state-of-the-art British ship measuring 300 tons, 102 feet long, and sporting a total of 18 guns. Rather than torture and burn, Black Sam traded his lesser boat for the crewman and captain to carry on in.

 

Madame Cheng

Madame Cheng was not your average pirate. While the “black beard’s” of the Caribbean held a healthy reputation and a modest crew, Cheng was Next Level.

Commanding an army of 1800 ships and 70,000 men, she thrived by collecting protection money from coastal cities and loot from ships in the South China Sea before living out her days as a successful large-scale opium smuggler.

 

BlackBeard

Less commonly known as Edward Teach or Edward Thatch, Blackbeard was an English pirate operating in the West Indies and the eastern coasts of Britain’s North American colonies. His gruesome appearance and habit of always being armed to the teeth and ship (the Queen Anne’s Revenge) armed with 40 cannons created quite the reputation – so much so that he rarely had to use any actual force.

His most famous battle involved the blockade of a port off of South Carolina, ransoming the port’s inhabitants. Blackbeard was eventually hunted down and killed by a group of soldiers in 1718.

Tales of his life have been exaggerated and has spawned the archetype of the tyrannical pirate that we’re all familiar with today.

 

Henry Avery

Henry Avery is the most famous pirate you’ve never heard of. Dubbed the “The Arch Pirate” and “The King of Pirates” by his peers, Avery was one of the very few pirates of note to retire with his fortune and life intact… and What a fortune!

His infamous raid, which spawned tons of literature and inspired many to take up piracy, involved a vessel making its annual pilgrimage to Mecca. He made off with over $66 Million worth of jewels and precious metals in today’s dollars. This resulted in a massive manhunt and bounty , but Avery managed to avoid capture and slipped into obscurity to live out the remainder of his days.

While we don’t condone the actions of any of these infamous pirates they all had one thing in common, their love of the water! If you are interested in getting on to the water you can take a look at what we have to offer.

Remember to share the fun on social and check back often for more great lists, helpful tips, and useful DIY guides.

Yours in boating,