History’s Most Famous Pirate Boats

Which pirate boat was the most feared and infamous in history? Pirates have been a curse of the maritime world almost since ships first sailed. Despite their deep roots in seafaring culture, most pirates’ backstories continue to be shrouded in mystery. Many merchant ships transporting hordes of money and valuable goods were plundered by the most ruthless pirates the world had ever seen at times when piracy was at its peak.

Pirates had a lot of powerful advantages, including their famed ships, which had been expertly prepared to not only survive the storm waves of some of the world’s most hazardous seas but also to vanquish their naval opponents via the barrels of their massive cannons. The mere sight of one of these ships was enough to make their opponents surrender. To celebrate this year's International Talk Like a Pirate Day, we will take a closer look at fear-inspiring vessels that eventually became famous boats in history.


flying dutchman famous boat

1. The Flying Dutchman

flying dutchman famous pirate boat

The Flying Dutchman was a well-known pirate ship of legends. According to European maritime folklore, the appearance of the Flying Dutchman, a phantom ship doomed to sail forever, is a portent of an impending tragedy. The ship is haunted; some sailors call it “the ghost ship.”

Richard Wagner’s famous opera Der Fliegende Holländer (1843), which takes place in the same world as the ship when it was first sighted, was inspired by the most popular version of its story. In this version, Dutch Captain Vanderdecken risks his life by promising to journey round the Cape of Good Hope during a storm and is subsequently condemned to sail around the Cape for the rest of his life.

Another legend speaks of a Captain Falkenberg, who spends his whole life at sea waging a dice game with the devil for control of his immortal soul. Similarly, in Rime of the Ancient Mariner (1798), written by English poet Samuel Taylor Coleridge, the doomed mariner protagonist sees a ghost ship where the characters Death and Life-in-Death play dice with him to bring him back to life.

The Flying Dutchman has been widely discussed in print for over two centuries. Many witnesses have reported seeing a ghost ship with full sails, and some have even claimed to have followed it as it sailed through fog or stormy weather.

Many others, however, claimed to have seen the ghost ship making rapid pace across placid seas, which is at odds with other stories of its appearances. Many reports of the ghost ship have been made near the Cape of Good Hope and its surroundings ever since the legend began in the 1600s.

Some of these sightings have been reported during periods of extreme weather, when gales were battering the peninsula’s coastlines. Written reports describe the ghost ship as being caught in a storm and on the verge of colliding with rocks before vanishing into thin air. It might be able to be dismissed as pure fiction at the end of the day. Still, as it’s been described, this mythical vessel is the biggest, baddest pirate ship ever built.

2. Queen Anne’s Revenge

queen anne's revenge famous pirate ship
This ship is a favorite of many pirate fans. One of the most infamous pirates of all time was Edward Teach, better known by his more popular moniker, Blackbeard. In November of 1717, Blackbeard took possession of the French slave transport ship La Concorde.

He added armaments to the Concorde and rechristened her Queen Anne’s Revenge in honor of the British monarch. From his ship, which he had equipped with 40 guns, Blackbeard dominated the waters of the Caribbean and the east coast of North America.

In 1718, the crew of the Queen Anne’s Revenge was forced to abandon ship after running aground off the coast of what is today North Carolina. Divers discovered what they believe to be the sunken Queen Anne’s Revenge in 1996.

3. Adventure Galley

In 1696, Captain William Kidd, a Scotsman who had settled in the then-British colony of New York, was on the verge of becoming a major player in the field of ocean exploration. He was a bounty hunter who, in 1689, claimed a large French reward and went on to marry the heiress of a rich aristocratic family. He convinced a number of well-to-do acquaintances in Britain to back a privateering expedition in 1696.

After outfitting the 34-gun Adventure Galley, he sailed out to the Caribbean to hunt down French warships and pirates. To help him in his mission, the Adventure Galley had 23 oars for use in light breezes.

However, it was discovered that tracking down pirates was no easy feat. Kidd had made a commitment to pay back the money he’d been loaned. When he failed to return with any booty after it became impossible to find the pirates, he attacked British-allied ships to make up for his failures.

Kidd’s Adventure Galley, which he abandoned in 1698 off the coast of Madagascar, later developed a decaying hull. After New York government official Robert Livingston denied Kidd’s request for clemency, Kidd was sent to London, where he would spend the next several years in jail until being executed for piracy in 1701.

4. Royal Fortune

During his three-year career, famed pirate Bartholomew “Black Bart” Roberts seized and plundered hundreds of ships. During this time, he sailed many different flagships on his travels, and he christened them all Royal Fortune. The largest Royal Fortune, manned by 157 crewmembers, was a 40-cannon behemoth capable of taking on any ship in the Royal Navy of the day.

Roberts was slain in violent combat against the HMS Swallow in February 1722 while serving as captain of the last Royal Fortune.

5. Whydah

Originally constructed as a slave transport ship, the Whydah left London in 1715 in search of African slaves. The ship got its name from the alternate spelling of Ouidah, a port city in what is today the West African nation of Benin.

Slave trafficking between Africa and Europe, known as the “triangular trade,” was partially facilitated by this 300-ton ship captained by Dutchman Lawrence Prince. With its tremendous speed, the Whydah was capable of traversing the seas at up to 13 knots.

While the Whydah was making a second voyage between Cuba and Hispaniola, pirates under the leadership of “Black Sam” Bellamy seized the vessel in the Windward Passage. The pirates took the ship and its crew hostage, using it as their flagship.

A Nor’easter forced Bellamy and his crew to turn back as they sailed north along the eastern coast of the American colonies. On April 26, 1717, the Whydah was trapped by the storm, disintegrating upon striking a sandbar off the coast of Cape Cod, and it sank with an estimated $50 million in treasure aboard. The ship’s initial crew of 146 was reduced to only two survivors.

In 1984, professional treasure hunter Barry Clifford discovered the ship and subsequently salvaged over a hundred thousand artifacts from the wreck.

6. Delivery

The Gambia Castle (later rechristened Delivery) was a moderately sized English Man of War aboard which George Lowther served as second mate during the ship’s 1721 trip to Africa. The Gambia Castle was en route to a coastal fortress in Africa to drop off a British garrison when an unforeseen incident took place; the soldiers arrived to find dreadfully insufficient housing conditions and food supplies.

Since Lowther had lost the captain’s favor, he was able to rally the angry troops to mutiny against him. Together, they stormed the Gambia Castle, renamed her Delivery, and sailed off to undertake in piracy.

Eventually, after a lengthy career as a pirate, Lowther decided to sell the Delivery in exchange for a more robust craft, a decision that ultimately proved fatal. Abandoned on a deserted island after his ship vanished, Lowther committed suicide rather than be captured by British sailors nearby.