15 Gruesome Pirate Love Stories To Rock Your Boat

Sailing off into the sunset with love on the horizon is so cliche. Unless, of course, your ship is a frigate, your sail is set for oblivion, your crew is comprised of bloodthirsty, plank-walking cronies and your lover is a pirate, just like you. This is when things get interesting. As you read on, you'll learn that pirates were a whole lot like everyone else except that their dice were made from people's bones, they terrorized all ships on open water, and they challenged royalty, questioned legality, and defied the laws of land. Even in present day, life on the open water is quite different; quite daring if you will. For when the sun sinks beneath your realm of vision and everything goes dark, it is your lover's heart that you will cling to. Albeit that heart may be removed from their body and lying in your hand bloody and torn, but a pirate's love is everlasting- as you will soon find out.

There are some points you should bear in mind about pirates if you truly wish to understand the depth of their love. Many of them were born under the harshest of circumstances. Many of them were running for their lives. Many of them had narrowly escaped the horrors of severe poverty, slavery, and prostitution. Many of them were looking for death when they found the sea and later each other. As such, their quarrels were fierce, their tales were legendary, and their legacies are still just on the brink of revelation. Here are 15 gruesome pirate love stories to rock your boat.

15 Romantic Flames On The Fury


Pretty Peg was a beauty with an amazing set of sea legs. Her husband, a wealthy Dutchman by the name of Hendrick Van Drake would do just about anything for her. On the edge of the seventeenth century while along the coast of Holland, it appeared as if their love boat had sailed but fate was about to deal them a rather unexpected hand.

In an unforeseen twist of events, the wealthy Dutchman's crew committed mutiny, stripping Van Drake and his new bride of their entire fleet of ships and leaving them stranded with a handful of loyal comrades and one small boat, aptly named "The Fury." The noble Dutchman almost returned home at a loss but his new bride convinced him to chart a different course centered on money, power and, you guessed it, revenge.

For many years, during the notorious Holland wars, Van Drake and his Peggy terrorized the sea, taking what they wanted and living as they pleased. One fateful night, while seizing an enemy ship, Pretty Peg was banefully shot down, never to breathe again. In a cruel act meant to taunt the Dutchman, her lifeless body was delivered to him via a small group of adversaries. When he saw her lying limp and dead, his heart was broken. He punctured the Fury in the middle of the ocean, intentionally sinking himself, his ship and his recently deceased wife.

14 Love Conquers Cannibalism


When a pirate eats your heart out, it might not be a metaphor. Such was the case in this tragic tale of star crossed sea rovers who, as it turns out, were very happy to meet each other. Our saga begins on the streets of London, when a buxom belle by the name of Charlotte was held captive by a fervent captain and forced into a marriage she loathed. As her hatred for her captor grew, young Charlotte developed a penchant for swordplay and a passion for lopping off people’s heads. Legend has it, she beheaded many, beginning with the unwanted husband who screamed out in agony just before the fatal blow. This is what she did to the man she didn’t love. What she did to the man she did love was far worse.

Her life as a pirate was on course throughout the mid-17th century. Her name and reputation were widespread but while sailing the great beyond, she still managed to find romance. It came in the way of a Spanish conqueror who was happy to join her in a life of crime. Together, they took lives, looted ships, and ruled the sea. Then, one ill- fated journey washed all the good times away.

On their way to France, Charlotte, her lover, and her crew were shipwrecked. Would you like to know how they lived to tell the tale? They drew straws. They didn’t draw straws to figure out who would wander off in search of food or assistance. Oh, no. They were pirates. They drew straws to figure out which one of them would be stabbed to death and eaten so the crew could survive. Sadly, Charlotte’s sweetie drew the shortest straw.

13 Jean de Belleville's Revenge


If you liked Braveheart then you'll love this one. Jean de Belleville wasn't a pirate. She was a rural housewife and noblewoman, raising her two sons in the quiet countryside in a region that was under siege by the French. Her love for her husband was intense and everlasting. So when he was brutally murdered at the hands of French soldiers, she sought vengeance at the edge of a sword. Taking her young sons with her as companions, this former modest housewife left the sea bleeding red from her pain (see the above engraving of her ship in action). Jean de Belleville torched entire cities and brought French aristocrats to their knees. Although there was a bounty on her head, this maritime maiden was never captured. She simply drifted out of existence like the tide she rode in on.

12 Summer With The Sea Marauders


Rachel Wall and her hubby George Wall lived a quiet life in rural Pennsylvania. That is until the summer. That's when everything would change for the married couple. For this dangerous duo were seasonal pirates, throwing up false distress signals on the water in an attempt to lure strangers in. Whoever was kindly enough to offer them assistance was brutally slaughtered in the sea. After the killings, George and Rachel would return home with pockets full of silver and boats weighed down in gold. Talk about a hot summer vacation. Who knew that pirating could be a part-time job; hopefully nobody else will figure that out.

11 Leaving Behind An Empire


Lars Gathenhielm was disabled and dying. His wife was the modest daughter of a mill owner. He desperately wanted to leave his wife some security after he died. Knowing little aside from how to commandeer a ship, Gathenhielm turned to the Swedish government for help. They made him a “legal pirate” which was a complicated scenario entrusted to few and understood by even fewer. In some cases, he was also accused of actual pirating but the two were so similar that in hindsight, it’s difficult to determine the legal from the illegal. At any point, his life at sea was all in the name of his family and when he passed away, he left his lovely wife a great deal of legal money, regardless of how he went about earning it.

10 Blackbeard And The Ladies Of The Port


Donning a vibrant, feathered tricorn hat, barricading the mouth of the Charleston Harbor, battling with multiple bullets lodged in his throat, shooting his first mate in the face and attempting to actually raise hell to earth--- these are all things that Blackbeard, one of the most famous pirates of all time, has been accused of. Being a steamy, powerful lover on the other hand...well that certainly wasn't in the original description. New archaeological discoveries however, have brought new revelations of the wild, bearded pirate we've come to know. Ones of a nautical lover.

As it turns out, the legendary Blackbeard is now thought to have been "madly in love " with not one, but several "ladies of the port." He is believed to have married at least fourteen of them, adorning them in treasure beyond their wildest dreams. The verdict on this one is still out but it appears as if Blackbeard liked to get his treasures in the ocean and his booty in the port.

9 Passion On The Guangdong Coastline


Here's one that proves one's normal life can change really fast. Cheung Po Tsai and his wife were already a devoted couple, married and settled in a small fishing town, but poverty was putting a strain on their relationship. The two skipped couples' therapy and dove straight into pirating, amassing a vast fortune along the way. At the end of their short lived but vivacious expeditions, they retired to a secluded cave on the coast of Guangdong, never to be seen or heard from again. Now that certainly is romantic! Although we're not sure what they did with all their treasure. Hmmm, treasure hunt, anyone?

8 Love/Hate Relationship On The High Seas


Some say that the only thing that roars louder than the clash of two Irish tempers is the sea itself. Meet Grania O’Malley, a ferocious widow hailing from a long line of strong but noble seafarers. When the opportunity presented itself, Ms. O’Malley controlled the trade and traffic off the coast of Clare Island, commanding more than 200 men- but her heart only belonged to one.

Things between Richard Burke of Scotland and Grania O'Malley of Ireland weren't always smooth sailing. Together, their pirating was so infamous that even the queen had to tip her hat. In an effort to end the wild couple's relentless reign, Richard was knighted and Grania was made a lady, although, of course, she still donned male clothing, as was the protocol for female pirates back then in the early 1600's. The two were then declared legal pirates .

Meanwhile, back on their homefront at Rockfleet Castle, a towering, stormy abode that let in barely a crackle of sunlight, the line between love and hate was growing thin. Curse words pierced the night. Occasionally shots were even fired. Initially, they were married but they hated each other so much that they divorced, yet they loved each other so much that they stayed together. Know anyone who fits this description?

7 The Persistent Lover And The Cold Hearted Snake


Young Alf of Denmark had fallen for a princess. But not just any princess. He had fallen for a pirate princess. Her name was Alwilda and her father ruled the Goth Kingdom in the 9th Century- at a time when kidnapping rich brides for ransom was all the rage. Alf's dear pirate princess was heavily guarded by a deadly, slithering snake and a promise made by her daddy...that any caught entering his daughter's quarters would not live to tell the tale.

Alf built up the courage to approach his pirate princess at the risk of snake venom and/or impalement. As such, he battled both the snake and her father and he won. He won everything except Alwilda's heart. Although she was now supposed to marry Alf, she turned instead to the sea and engaged in a life of crime as a female pirate; but Alf's love for her was more like a fatal attraction.

Legend has it that he followed her across the seven seas, climbed aboard her pirate ship and slew the entire crew. At this point, she could no longer resist his strength and so he married her aboard a Scandinavian ship and together they would end up taking control of Denmark both on land and by sea. Norse writings support this tale although the story wasn't actually transcribed until 600 years after it was told. So it's one of those things that went down as being either fact or fiction, depending on your fancy.

6 The Captain And His Willing Captive


Little is known of the late female pirate Madame de Fresne aside from the fact that she buccaneered the seven seas with a man who was her captor. Originally, he was holding her for ransom but apparently he wanted a whole lot more than just a captive. He was, after all, a pirate. But what started out as business soon got personal and the two fell madly in love. The sinister pirate's soft spot was exposed and he married her rather than ransoming her off. This pair plotted and plundered through the 1600's.

5 Anne Bonny And Everybody On Her Ship


Anne Bonny was a serial lover. And a pirate. And a woman. But she went down in history because she was so stinking mean that she shot a guy's ear off just for looking at her wrong. The fact that she chose his ear instead of his eye is already pretty telling. So if you're a pirate fan or a Disney fan or a Johnny Depp fan or just plain awesome (because you fit into all of those categories) then you might know that Captain Jack Sparrow was based on a real pirate whose last name was Rackham. You might even know some of Anne's story via his. But rest assured, the Cap'n wasn't Anne's only beau. He was one of many.

According to legend, Anne Bonny boarded his ship with her then husband James Bonny and she was sneaking into the captain's quarters as a side thing. When her pirate husband caught wind of the affair, he challenged his own captain, one "Gentleman Jack" to a duel. It's pretty clear that the Captain won but Anne still wasn't content. When new blood boarded the ship, she took a liking to a young thin sailor who turned out to also be a fierce woman sporting male attire. Anne's new flame was named Mary Read and she was almost as sinister as Anne herself. The two of them formed a non-platonic alliance and it wasn't long before Captain Jack grew suspicious.

In a fit of jealousy, he barreled into Anne's dwelling to catch her in the act with her new love. When he realized that the bed was abreast with, well, breasts, he dropped his sword and his pants and climbed between them. Anne, Mary and Jack went down in history as the first, and possibly the only, pirate ménage à trois.

4 The Red Flag Fleet Takes A Lady Of The Night


Madame Ching of Southern China is beheld as one of the most powerful female pirates of all time even if she came from very humble beginnings. Her story began in a brothel, a horrible and arduous place where she was forced to suffer through a life of prostitution. However, in a bizarre twist of fate, an elderly pirate took a liking to her and she escaped with him and his Red Flag Fleet. She was grateful for her freedom whilst he was smitten with her beauty. Together they stole over 800 ships, fired off 15 canons, barricaded the streams and rivers and filled their boats with gold bars, silk, spices and precious gemstones. So at least they had that going for them.  There's no word on whether he ever visited another brothel.

3 Black Caesar's Heart Bleeds Red With Love


Raiding slave ships was a common quest amongst pirates. The reasons for this are so complex that they're deserving of a novel or at least a separate post. For the sake of the story, it will have to suffice to say that new archaeological evidence is painting a completely different picture of the deep blue sea and African-American pirates had a huge role in it. You see, at the time, a real life horror known as slavery was playing out across the Transatlantic and many African-Americans, if given the choice, chose pirating over enslavement or flight. African-American pirates held high ranks. They weren't just fighting for their lives. They were fighting for their freedom. In the case of the infamous Black Caesar, legend has it that he fought and slew many in order to free his one true love. Was Black Caesar the real life Django? Only time and archaeology will tell.

2 Poisonous Lovers By Land And By Sea


Meet Hiram Breakes and Mrs. Snyde, two seemingly average Dutch citizens living mundane lives. Breakes was a sailor and Snyde was a housewife. Their whole facade crumbled when they fell in love, however. Together, the adulterous couple poisoned Mr. Snyde, freeing the maiden of her marital obligations in the process. Their love commenced from there and before they even had a chance to be wed, the widowed mistress became pregnant with the Dutchman's seed, a shocking predicament in that day and age. In order to hastily bring forth provisions, Mr. Breakes became a pirate. His murderous side really shone on the open water. He plundered the Balearic Islands and the Mediterranean, kidnapping nuns and robbing for gold. Meanwhile, his mistress was at home, attempting to poison their newborn baby. She was hanged and he committed suicide. What a great couple.

1 Samuel Bellamy And His Not So Merry Heart


This tale is one of an ordinary man who put himself in extraordinary circumstances---all in the name of love. Much in the vein of other timeless protagonists, a poor but ambitious gentleman fell for a woman of wealth and demureness and attempted to win her admiration with cold, hard, cash. Samuel Bellamy was one such guy and his love interest Maria Hallet was really just a shadow in the light of his legend.

This story began in Eastham, Massachusetts. When young Samuel failed at hunting for treasure, he looted for it instead. Calling himself Robin Hood and his crew Merry Men, his goal was to stock up as quickly as possible and head back home to his honey. He had collected more than 50 ships along with their contents in his short time at sea. He also lived to be one of the wealthiest, most famous pirates of all time. Sadly, after collecting more than 20,000 pounds of sterling silver, a storm struck and sunk his ship. He never made it home to tell sweet Maria that he loved her. His truth was later revealed in the found wreckage from his ships.

Sources: thewayofthepirates

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15 Gruesome Pirate Love Stories To Rock Your Boat