6 real-life swashbuckling pirate adventures

First of all, I just want to say that pirates did not make good people. They were born of war, an inconvenient by-product of many naval conflicts and as such were brutal, unforgiving sea folk. But there is a reason that in the centuries since Blackbeard stalked the Carolina coast and Bartholomew Roberts first raised the jolly roger, pirates have been romanticised and imitated.

The new world to those of the 17th and 18th centuries was like space is to us in the 21st. What were in effect just common criminals became folk legends, walking the plank between fiction and reality. Piracy in the new world was exciting, revolutionary and politically challenging, but overall it was tempting.

The following tales are real (to the best of our knowledge), taken mostly from contemporary accounts of crew members, captains and victims, Committed to paper by captain Charles Johnson (probably a pseudonym for Daniel Defoe). So pour yourself a tankard of the finest grog, put your feet up (wooden or otherwise) and put your parrot away for ten real-life swashbuckling adventures.

#1 Captain Worley's humble beginnings

With the tales of mighty pirate fleets and gilded galleons, you would be forgiven for thinking that to be part of the 'arrrrg' club you first need a ship, something capable of fending off the competition, not to mention the pesky British navy. This pirate legend, however, proved that pirating is anything if not inclusive, that everyone has to start somewhere and that the step by step to becoming a terror of the high seas is simple; get dingy, get a ship, get a bigger ship.

In the September of 1718, just as the golden age of piracy was coming to a close, Cpt Worley and his modest crew of eight set off from New York in a small open-top boat with just a few provisions and as many muskets as they could carry. Their sights were set on the Delaware River 150 miles away. They soon arrived and set about looking for small prizes, but with little to pray on but other small open-top boats, and with their element of surprise gone, Cpt Worley ordered that they head back out to sea.

As their overcrowded vessel reached the mouth of the Delaware, a sloop loomed into view. It was the Philadelphia, belonging to pirate Cpt Black Robin. Cpt Worley and his few men boarded and commandeered the vessel along with its crew, leaving Cpt Black Robert to Davey Jones's locker.

Cpt Worley and the Philadelphia went on to take many ships and much treasure in the months they sailed the seas until February of 1719 when his life choices (and the navy) caught up with him. An epic battle ensued in typical pirate fashion, seeing an end to the crew of the Philadelphia and its Capitan.

#2 Mary Read

One of the most fearsome pirate captains to sail the Americas, Mary read was a fighter from birth. At the age of thirteen, disguised as a boy, she joined the crew aboard a British Man’o’war. For some time she managed to stay concealed and learnt all she could about life, and battle, at sea. Looking to change things up, Mary fled to Flanders where she carried arms for a foot regiment. She proved her bravery time and again both in naval and land conflicts, until falling in love with an officer named Fleming.

After revealing herself, they were soon married. This, however, wasn’t the life that she seemed destined for (What’s a pirate's life without tragedy?) Fleming died just a few years after their marriage.

Without any skills other than being a worrier, Mary Read joined a privateering vessel destined for the Caribbean. Upon arrival, and before any legitimate privateering could be done, Mary Read led her crew to mutiny, placing her as captain.

In the following years, much successful pirating was done, with villainous collaborations formed and many battles won. In one such instance, her ship was set upon by another vessel. All who were on her ship cowered below deck leaving just Mary read and fellow pirate Anne Bonney to fight. As the opposition started to board, withdrawn cutlasses Cpt Read shouted to the crew below ‘come up and fight like men!’

#3 Captain Morgan and his ransacking of Panama

Captain Henry Morgan, no doubt a name you’ve seen before on the label of the popular rum, Henry Morgan was much more than his namesake beverage. He was possibly the most successful pirate of his era. Henry Morgan has given tell to many a tale of buried treasure and epic adventures through the interior of unknown lands, the most audacious of which was his role in the ransacking of the city of Panama.

Captain Morgan was doing well as a pirate, taking many prizes along the Spanish Maine, from sloops to galleons but it just wasn’t enough. To cement his place in history he had to do something truly grand, a heist for the ages. There was tell of a Spanish city, glittering with golden alters that if taken would set Morgan and his men up for life - Panama.

Panama was one of the most heavily militarized cities in the new world. There were high walls, there were formidable gun batteries and thousands of Spanish soldiers. Certainly, no matter the manpower, Panama was not to be taken from the sea. He used his charm and experience to form a formidable fleet of buccaneers, ships and over 1000 men. The plan was simple - sneak around the back. Captain Morgan sailed his flotilla to somewhere near modern-day Colón and marched his army inland, through the jungle. For weeks they marched, through starvation, disease, uncharted lands, meeting creatures that no one had seen before until finally, they reached Panama.

the long march through the interior meant the Spanish had been expecting them and were ready with over 3000 men. Being the pirate badasses, they overcame the terrestrial troops and laid siege to the city only to be disappointed. The Spanish had prepared. They had whitewashed the golden alters and taken away the majority of treasure to ensure that it stayed in the hands of the king. The battered pirates retreated into the jungle with almost nothing and headed back to their fleet. Or so Captain Morgan would have us believe.

It has been said that the majority of the gold and jewels that the Spanish hadn’t managed to hide was stolen away from Morgan's men, buried in an undisclosed location, never taken back by the captain. Morgan lived the rest of his days in the Caribbean and died of natural courses at a ripe old age, never retrieving buried Spanish gold.

#4 Sir Francis Drake and the Cacafuego

Now this one is a bit of a matter of perspective. 400 or so years ago, depending on your allegiances, sir Francis Drake was either a pirate ( nicknamed el Drogo by the Spanish) or a hero. But one thing was certain, he was feared internationally.

Drake and his flagship ‘the Golden Hind’ formally the pelican (named the golden hind for one of his sponsors, times don’t change right?) circumnavigated the globe doing all sorts of piraty things, but perhaps the most audacious was the capture of the Cacafuego. The Cacafuego was a Spanish treasure galleon homeward bound with more gold, silver and jewels than you could shake a cutlass at. It was also a mammoth of the sea, bristling with cannon and Spanish soldiers, a fortress compared to the relatively tiny golden hind.

Luckily, it was not Drake’s first day on the job. He quickly ordered his crew to tie barrels and lose cargo to the back of the ship and throw them in the water, put on full sail and raise a false flag, making the golden hind look like nothing but a slow, heavily laden merchant ship. It worked. The Spanish galleon pulled right alongside to investigate.

Unsuspecting and with Drake’s crew hiding below deck, they tried to make contact. On Drake’s order, the golden hind lay round of cannon into the Cacafuego’s side while raising the true colours. Without any hesitation, the captain of the Cacafuego surrendered, making Drake, his crew, and his country, immensely wealthy.

#5 Captain Avery and his pirate origins

Captain James Avery, born in Plymouth, Devonshire was a bit of a mythical figure, even when he was still around. Those back home would tell stories of a pirate king who married a mogul’s daughter. A man who sat in the Bahamas surrounded by booty, such that they said that there was a play written for him called ‘ The Successful Pyrate’.

While Cpt Avery did have many adventures as a real pirate of the Caribbean, he ended his days in a small Devon town called Biddeford, waiting for a call back from some better pirates, probably hearing his own stories being told by someone on the next table in the tavern

Captain Avery was a real swashbuckling, double-dealing, treasure hungry pirate at his height. Hired by the Spanish to privateer against the French, he set sail on the ‘Duke’, a 30 gun ship with 120 crew under Captain Gibson and headed for the Caribbean. Throughout the journey, Avery allied with 20 of the strongest crew and hatched a plan to take a shortcut to the top.

Captain Gibson was a bit too fond of the grog, (if ya know what I mean), and so as usual, had gone to bed early. Avery, after rallying his men, gave the command to way anchor and set sail. Sometime later, a confused, hungover Captain Gibson called for Avery to ask why the ship was moving. Calmly, Avery said ( in a very piraty way) “put some clothes on and ill let you into a little secret” once dressed, Avery said, “I am the captain now and so would appreciate it if you left my cabin” they dropped Gibson off at the nearest island and made for Madagascar.

#6 Captain Skinner and his crew’s revenge (captain England)

This is a story of revenge amongst the crew of pirate Cpt England to understand, we need to go back a while to a privateering vessel sailing off the coast of Africa. Now, the accounts are sketchy, but it seems that there was a fierce altercation between one Captain skinner and some of his men. It was so fierce in fact, that Cpt saw fit to place this group of men aboard a British Man’o’war without payment of any final wage. Soon, and with vigour, said crew members found a method of desertion and found themselves aboard the pirate ship of Cpt Edward England bound for the Caribbean.

For the next few months, they took part in all manner of pirate activities until they happened across a familiar vessel. They approached, raised their colours, and the prize lowered theirs in response. Captain England ordered that the defeated captain come aboard. Much to the surprise of the crew, the man that came aboard was none other than Captain Skinner. It was at this point that Cpt skinner discovered that not paying his men was perhaps not such a good idea.

the slighted men immediately tied Cpt skinner to the windless, belted him with anything they could find, pushed him about the deck, and finally, because he was said to be a good captain to the rest of his men, got rid of him quickly. I guess it just goes to show, don’t mess with pirates

#7 Captain Martell between September 1716 - January 1717

Captain Martel was a formidable foe if a short-lived one. With his sloop of just eight guns and his trusty crew of 80 men, he went on a crime spree so epic that it’s remembered over 300 years later. Starting in September 1716 and ending badly in January of 1717, the prizes he took are as follows; the Berkley - the galleon of Captain Saunders, ‘King Solomon’ - a sloop, two sloops- The Martha and the John of Captain Wilson, an unnamed sloop and an unnamed brigantine, a twenty gun stout ship named the Dolphin, the Kent - another gallon, an unnamed galleon sailing off the coast of Jamaica, an additional three ships of unknown origin, and the Greyhound of Captain Evens.

Amongst the cargo he captured was gold dust, elephants teeth, fine silks, a fortune in coins, and enough provisions to ensure that his crew were happy and well-fed throughout all of their voyages. As pirates go, Captain Martell was peak, but it couldn’t last forever. Pirates tended to get cocky, particularly when they were taking prizes as frequently as this one was. Inevitably, Martel was pursued relentlessly by the British navy, and its most famed hunter - the Scarborough of captain Hume. In desperation, Captain Martell and a few of his men fled into the then forest of Santa Cruz with all they could. It is presumed that this is where they met their end, as Capitan Martel and his men were never seen or heard from again.

What do you think? Was this the end of the Wiley captain? Or did he escape with some of that treasure and live out the rest of his days as a wealthy man, surfing the beaches of Santa Cruz?