Show Mobile Navigation
Mysteries |

10 Unsolved Pirate Mysteries That Will Shiver Your Timbers

by Joe Drury
fact checked by Jamie Frater

Since the advent of sailing, there have been those who’ve traveled the seas in search of new lands, fortune, and hope. However, there have also been those with the sole purpose of plundering and destrcution. These people are commonly known as pirates. Pirates are notorious for having no mercy and doing almost anything in order to reap a reward. The main era for pirate activity was the 17th to early 18th centuries. It ultimately died down due to naval forces becoming too strong to combat. Although there are still a number of pirates around today, the last great pirate crews died hundreds of years ago, taking countless mysteries with them to the oceans’ murky depths.

10 The Ghost Ship Of Topsail Island

A famous strategy used by many pirate crews centered around Topsail Island was to wait for a ship to pass on the horizon and then chase it down and take the loot. This method proved to be extremely successful, as there was a lot of traffic passing the island in the early 1700s. The most infamous pirate to use the method was Edward Teach, alternatively known as Blackbeard, a 183-centimeter (6′) man known to be a master of physical and psychological warfare. Blackbeard was said to sometimes tie cannon fuses or sulfur matches into his beard as he fought in order to unnerve his opponents and show that he had no fear.

While there is rumor of treasure buried on the island, the most unsettling mystery is how Blackbeard’s ship is reported to eerily appear every so often. Some say that if you’re sailing with a radar, as you pass Rich’s Inlet, you can sometimes notice a blip on the screen, sitting inside the cove. When the area is scanned, nothing is there, but as you cruise by, the blip is said to slowly move toward the location of your ship, gaining rapidly in speed as it goes, just as Blackbeard’s ship did hundreds of years ago.[1]

9 The Treasure Of Oak Island

Photo credit:

A small island lies off the shore of Nova Scotia, Canada. This place is known as Oak Island, and it is home to an age-old pirate mystery. In 1795, Daniel McGinnis discovered a large, unnatural depression in the ground while crossing the island. When the area was dug into, a layer of oak planks was found every 3 meters (10 ft) below the surface. Below a certain number of planked layers lay a stone with symbols carved into it. These carvings are said to tell of a great treasure buried deep beneath the ground. The planks buried deeper down collapsed when reached, leading to the pit filling with water. This find has lead generations of excavators to attempt to access whatever is at the bottom of the pit, but nearly every attempt has ended in disaster. So far, seven have died while endeavoring to uncover the mystery, leading some to believe that the area is cursed.

What lies at the bottom of this traitorous pit is still unknown and possibly always will be. However, a great number believe that it is the treasure of Captain Kidd, a pirate known to have been operating in the area at the time, who famously stated that his fortune was buried “where none but Satan and myself can find it.” It is still a mystery as to how anyone could have secured the contents so well, leaving even 21st-century excavators clueless about how to uncover whatever is down there.[2]

8 Murder At Sea

Photo credit: YouTube

In 2014, a video was released of four unidentified men, believed by some to have been pirates and by others to have been fishermen, clinging to the wreck of an overturned boat. They appear to be holding their arms in surrender, but the crew of the ship is shown to be shooting at them while a voice on a speaker shouts “Shoot! Shoot! Shoot!” The crew appears to be laughing as they pick off the men one by one, and after the death of the final victim, they pose for pictures on the deck.

The identities of these men are still unknown, but what makes this even stranger is how the footage was found on a mobile phone left in a taxi. Despite there being a large amount of witnesses, no one has come forward, and the murder of these men still remains a mystery. However, it shows how easy it is for murder at sea to go unnoticed.[3]

7 The Kraken

Photo credit: Wikimedia

To most, the prospect of a giant squid capable of destroying ships and living at incredible depths would seem like nonsense. However, there may be more to the pirate legend than initially considered.

Paleontologist Mark McMenamin thinks that he has found signs of a large squid-like creature by investigating the bones of a 14-meter (46 ft) ichthyosaur. The bones are said to have been organized in the same way as octopus species will sometimes arrange bones, and they are also thought to have been under high pressure, indicating that the creature responsible dwelt in an extremely deep part of the ocean. McMenamin has also discovered a more compelling piece of evidence, which comes in the form of a fossilized segment of a giant octopus’s beak.[4]

Though the legend of the kraken is a very entertaining one and was almost certainly based on some form of encounter with a large sea creature, there is no real evidence that it ever existed. Whether it be a product of a drunken sailor’s imagination or a tale passed down over generations and distorted into something else entirely, the origin of the mystical behemoth remains a mystery.

6 The Cryptogram Of Olivier Levasseur

Photo credit: Wikimedia

In the late 18th century, pirate captain Olivier Levasseur, also known as La Buse, was one of the last great pirates roaming the Indian Ocean. He was known to have stolen many items of value and was thought to have a huge haul of treasure. However, he was captured and sentenced to death by hanging. Allegedly, he spoke his final words, “Find my treasure, the one who may understand it,” and threw a cryptogram into the crowd.

To this day, people are still trying to decipher the instructions, with many having given up long ago, believing that the cryptic message was just a joke to lead people on a wild goose chase. However, in the mid–20th century, a breakthrough was made by an Englishman named Reginald Herbert Cruise-Wilkins. He had been actively searching for the treasure for years, certain that it was buried on the small island of Mahe and was worth around £100 million.[5] A number of years earlier, Cruise-Wilkins had unearthed a number of pirate statues that were buried beneath the ground, but he was adamant that they weren’t just statues but rather a map to where the real treasure was located.

Reginald finally found the exact location he thought to be the treasure cave and began exploring, although it required very complex engineering work to ensure that the cave did not get flooded by the ocean water above. While in the cave, he was nearly killed by a rockslide, but he did manage to get away with a flintlock pistol, carved figurines, a 17th-century wine jug, and a few coins. This was enough evidence to suggest that it was in fact, the location of the treasure. However, no one was willing to further fund his project, leaving the treasure’s existence a mystery.

5 Pirate Utopia

Legend tells of a pirate utopia named Libertalia on a small island off Madagascar.[6] This haven was a pirate republic/anarchist colony founded in the late 17th century by pirate captain James Misson. Other founders included the famous pirates Henry Avery and Thomas Tew, the latter being the admiral of Libertalia’s fleet of ships.

The politics of the haven were generally socialist, with all food and resources being shared as well as all viewpoints being listened to and laws being created by the people. The pirates went off the motto “for God and liberty” and flew a white flag in protest to the Jolly Roger, which typically supports violence. They also were strongly against slavery and freed any slaves they came across, treating them as equals and allowing them to join the enclave.

The pirate territory was said to have a fort, a market, and housing covering the island. It was also said that the community thrived on the lands, building a full range of buildings, including great halls, places of worship, and taverns. Charles Johnson’s A General History of the Pyrates claims that the pirates, renouncing their nationalities, named themselves “Liberi” and created a new language. Johnson also said that Avery decided on the area of settlement as soon as he saw the bay, for it was an area with fertile soil, fresh water, and friendly natives.

The utopia was said to have fallen when Tew became stranded, leaving the haven effectively defenseless and leading to it being attacked. Misson and 45 other men were said to have escaped, but they never returned to Libertalia.

4 The Green Flash

Photo credit: Brocken Inaglory

For hundreds of years, men of the sea, most notably pirates, have repeatedly reported a strange phenomenon that has come to be known as the green flash.[7] It is said that when the sky and the horizon are both completely clear, a sudden flare of emerald-green light can flash across the sky as the Sun sets.

Reports of the flash go all the way back to the 1600s, with pirates being the ones who reported it most, as they would have had the longest sea voyages. While this phenomenon has a completely rational explanation, pirates claimed that anyone who saw the flash would gain the ability to read the souls of others.

3 The Ghost In The Cave

Photo credit: John Dyer

While on holiday in Cornwall, England, in 2015, businessman John Dyer accidentally captured something peculiar on his camera.[8] The man had been taking pictures of darkened caves, and when he reviewed the images, he spotted a shadowy figure standing toward the back in one picture. The supposed “ghost” is said to be that of notorious pirate William Wilcox, who operated around that area. It was thought that Wilcox was on the run and decided to hide in one of the nearby caves, but he became trapped by the rising tide and was consequently drowned.

While most believe the picture contains nothing more than an oddly set out rock formation slightly resembling a man, a number of locals are confident that it is indeed the ghost of Wilcox, the subject of many stories they were told as children.

2 Pirate Tunnels

Beneath the city of Savannah, Georgia, lies a network of underground tunnels believed to have been used by pirates to smuggle stolen loot and captured sailors.[9] There is said to be a secret tunnel somewhere in the labyrinth leading directly to the location where the ships would have been waiting.

Allegedly, there is a passage from a building in town known as the Pirates’ House that leads straight to the river, where small rowing boats would have been waiting, but it is now inaccessible from the house due to a rock collapse. There are also theories that the Sons of Liberty used to meet in a secret underground cavern that can be reached by the tunnels. Whether these tunnels were used by secret societies or pirates smuggling stolen goods, there is no denying that they are indeed rather strange.

1 Lake Of Bones

Photo credit: Patch

Long Island’s Lake Ronkonkoma is well-known for the mysteries and legends that surround it.[10] One of the most famous mysteries is that of the pirates’ victims. Some say that the lake was once connected to the sea through an inlet, allowing pirates to enter the area, hide their treasure, and execute prisoners. Stories say that the bottom of the lake has many caves that hold a large amount of hidden treasure that pirates left there long ago.

It is also told that the lake contains many skeletons of the pirates’ victims, some of which have allegedly been found and pulled from the water, although there is no proof to support this. If the lake really does contain the skeletons of hundreds of pirate prisoners, however, it may be a pointer to the location of treasure hidden in there.

Although many pirate mysteries lack proof and evidence, they are extremely interesting to speculate about, as very little knowledge exists for a number of them. However, someday, maybe one of us will guess lucky and uncover something truly amazing from the ancient world of pirates.

I’m Joe, a freelance writer and author with an interest in unexplained mysteries.


fact checked by Jamie Frater