7 Most Notorious Islands & Pirate Strongholds

"No renegade can rise to power on his own. He has followers, and together, they are invariably supported—either directly or indirectly—by the oppressed public or the ambitious government. Both have vested interests in the outcome of such clandestine patronage of otherwise unsolicited outlaws."

Privateers and pirates have always had deep-rooted, paradoxical ties with political influences, dynasties, or imperial powers. The colonial rulers understood their precarious presence at sea and used them to their advantage, enduring some losses while giving them just enough freedom to go about their business. They would then pull the leash when pirates and their clans became overbearing. Privateers and buccaneers often joined forces with European monarchs, Asian rulers, and international traders, undertaking various projects to assert supremacy on international waters and trade routes. In return, they engaged in their cutthroat ways—killing, plundering, marauding, looting small boats and merchant ships, and manipulating coastal regions. They would sell their loot to the affluent class, who, in a way, indirectly supported them.

Privateers and pirates were formidable mercenaries kept on the fringes by any nation involved in spreading domination across the world. With support from respectable societies and by utilizing their ruthless skills, pirates created both small and large armies, complete with fleets of ships and a great deal of ammunition. To operate such an army, they, of course, needed a base of operations. This brings us to the topic at hand: the most notorious pirate islands in the world during antiquity. These islands were well camouflaged from unsuspecting sailing ships. They were small islands with small communities, providing a safe haven to conduct nefarious activities. Some islands even served as the 'Switzerland' of pirates.

Pirates have sparked the wild imaginations of many writers, readers, and entertainers. With popular pirate stories capturing international attention, otherwise obscure islands found themselves becoming points of curiosity for travelers around the world.

Île Sainte-Marie – or St. Mary, is an island off the east coast of Madagascar in the Indian Ocean. It could well have been the utopian pirate republic of Libertalia, a fabled free colony founded by the pirate Captain James Misson for a community of pirates and slaves freed from captured ships. The island is a veritable paradise, with dense vegetation and tall coconut palm trees providing restful shade along beautiful stretches of sandy beaches, pretty coves, bays, and caves surrounded by coral reefs. Its tropical climate makes it ideal for spending days in peace and nights in leisure, with Malagasy music playing in the background.

The idyllic setting lulls you into slumber, but in the 17th and 18th centuries, this was a pirate base that harbored the likes of Adam Baldridge, John Pro, William Kidd, Robert Culliford, Thomas Tew, Olivier Levasseur, Abraham Samuel, and Henry Every. Founded due to its proximity to maritime routes used by ships coming from the West Indies, St. Mary’s pirates led many bloody attacks and plundered Indian ships for their riches and treasures. The looted cargo had ready buyers, including competing merchants, local traders, and aristocrats. Many original pirate vessels can be found near Baie des Forbans and the pirates’ cemetery nearby. Descendants of some of those pirates may still be living there in obscurity today.

Tourism – It is an excellent spot for diving and snorkeling; whales also prefer it for birthing and weaning their young. The channel between St. Mary and Madagascar sees many humpback whales. With its strong infrastructure and excellent hotels, the island has become one of the top travel destinations for adventure sports enthusiasts.

Tortuga Island is a Caribbean island that became one of the most infamous havens for pirates and privateers. The first Europeans to arrive here were Christopher Columbus and his expedition in 1492. Until 1625, Tortuga was a Spanish colony, after which the French and English settled there following their expulsion from Hispaniola by the Spaniards. The French returned in 1630 after a failed attempt to remove them in 1629.

Over the next decade, the Spaniards attempted to drive out the French and English colonists three more times. Still, their interim rule did little to stop the pirates, who continued to operate heavily out of Tortuga. By 1640, French and English buccaneers and some Dutchmen formed a coalition known as the Brethren of the Coast and even devised a code of conduct for their community. Together, they carried out massive raids on Spanish galleons in the Windward Passage. 

Considered great buccaneers, Sir Henry Morgan and François L'Ollonais often launched attacks on ships from Tortuga. By 1667, Sir Henry Morgan had been granted a 'letter of marque' by Sir Thomas Modyford, the Governor of Jamaica, which licensed him to attack and seize Spanish vessels. Tortuga was fortified to become a stronghold for Caribbean pirates and served as neutral ground. Pirates going on raids always had Tortuga to return to—where they could get drunk, get bawdy, and store their loot.

The brainchild behind these raids was essentially the colonial powers of France, later joined by England and the Netherlands, fighting against Spain and Portugal for dominance in the Atlantic and Indian Oceans. The privateers were, after all, puppets of the colonial powers, profiting from the wars waged among these nations for monopoly. Ironically, this opportunistic patronage of privateers came back to bite the hand that fed them, as many buccaneers turned on their benefactors after the peace treaties were signed. From then on, every ship, port, or plantation was fair game.

Tourism – Tortuga is now part of Haiti, a peaceful and beautiful destination for great one-day trips. Boat rides, snorkeling, and, of course, searching for hidden treasures in the caves are popular activities. The island is well-preserved, as there are no hotels or other infrastructure that allow travelers to stay longer than a day.

Port Royal – the most wicked and sinful place on earth. The town came about as a result of constant wars between European nations, all vying for control of Jamaica. Originally occupied by the Spanish, it was later seized by the English, who used Port Royal as a strategic base for access to Jamaica and its proximity to important maritime routes. During English rule, several attempts to capture Jamaica were finally addressed by Governor Edward D'Oyley, who invited French and English privateers, known as the Brethren of the Coast, to seek refuge in Port Royal. In exchange, the Brethren were expected to provide protection against Spanish and French invasions.

It was in Port Royal that the privateer Captain Henry Morgan launched his famous attack on the city of Portobello. He later went on to become the Governor of Port Royal. The town became a gathering place for pirates from all over the Caribbean: wicked deals were struck, alliances formed, and invasions planned by both privateers and the English alike.

The arrival of pirates and their unaccounted wealth brought about debauchery, prostitution, degeneration, disease, and all manner of excess. Port Royal’s infamy spread across the world, quickly attracting fortune hunters eager to partake in the wealth it was generating. Brothels and taverns dominated the port, catering to women and wine. The English and French gentry thrived on sugar plantations by exploiting slaves, who were brought in by hundreds of pirates as they saw it as a lucrative business. The town's ruinous ways grew rapidly, accumulating cursed wealth and loose morals, to the point that it can be said Port Royal did not see its comeuppance coming. In 1692, nature took over, and the town was drowned by a massive earthquake followed by a tsunami, destroying both the buildings and the people of the port.

Although pirates continued to stop by for a few more decades after the devastation, some of the most notorious pirates, including Blackbeard (Edward Thatch), Charles Vane, Calico Jack, Mary Read, and Anne Bonny, made Port Royal their base. Charles Vane, Calico Jack, and many others were eventually hanged at Gallows Point as a result of anti-piracy laws, brought about by the townspeople's growing intolerance toward pirates and their ways. The pirates who had been accosted in Port Royal simultaneously began developing a stronghold for themselves in New Providence, Nassau.

Today, the infamous 17th-century town lies underwater, and what remains is in a state of disrepair, with little economic or political significance.

Pirates of the Caribbean is loosely based on Port Royal’s history, though it is far removed from reality.

Pirate Coast – was an area stretching from modern-day Qatar to Oman in the Gulf of Persia, dominated by the Al Qasimi tribe, which rules the emirates of Sharjah and Ras Al Khaimah today. For centuries, privateers, pirates, and smugglers raided Arab, Persian, Portuguese, and British merchant ships carrying precious Indian and Asian cargo.

European piracy was prevalent in the 16th and 17th centuries, with pirates raiding Indian vessels crossing the Gulf of Persia. However, in the 18th century, there was a shift in events when the inhabitants of the Gulf of Persia began conducting heavy, cutthroat raids on a large number of ships from their base at Ras al Khaimah. Some of the attacked ships were from the East India Company, others were merchant vessels of different flags, some were local Arab boats, and many came from Surat in India. The Qawasim viewed these raids as part of the traditional raiding practices that had long been a social and political norm in the region. Many engaged in piracy, likely in search of a better life than fishing, herding, or struggling to survive in the harsh landscape, especially since the discovery of oil had not yet been made. The stronghold of the tribal chiefs was Ras al Khaimah, and the Arab raiders, or “Jawasmi,” were often seen as fanatics who took pleasure in murder.

The British launched a massive expedition to eradicate piracy from the Pirate Coast, as their ships were constantly plundered, disrupting British trade, which was vital for their empire’s expansion into India and other Asian countries. The British sought to stabilize the tribes in the Gulf, as there was no unified political leadership. However, their noble-sounding intervention was, in reality, an effort to further their imperial ambitions. A peace treaty was signed between the Al Qasimi tribe chiefs and the British, but the treaty's stability was questionable, as the British remained determined to assert control over the Gulf.

During the 18th century, the most notorious pirate in the Persian Gulf, known for his ruthlessness, was Rahmah ibn Jabir al-Jalahimah. An English author once deemed him to be tolerant, likely because the pirate assisted the British in waging war against the Al-Qasimi of Ras al Khaimah. Rahmah ibn Jabir al-Jalahimah went on to rule Qatar for a brief period, thanks to his strategic alliances—first with the Saudis, and later, after abandoning them, with the rulers of Muscat.

Both islands share one common figure—the Haitian-born pirate, privateer, slaver, and smuggler Jean Lafitte (c. 1780–c. 1826). In the early 19th century, Barataria Bay served as the base for pirates, privateers, and smugglers led by Jean Lafitte and his brother Pierre. They ran an underworld gang that provided about one-tenth of the employment in New Orleans around 1807. The Lafittes’ pirate attacks primarily targeted Spanish vessels in the Gulf of Mexico. Lafitte later earned a pardon from the government for his role in defending the city against the British during the War of 1812.

Once again, the outlaw Lafitte developed Galveston Island, Texas, as another smuggling base. Lafitte claimed that these raids were legitimate privateering and that he held letters of marque to prove it, but a few years later, he admitted that he did not have a valid commission. Despite a law prohibiting the importation of slaves into any port in the United States, Lafitte secretly continued the slave trade through his stronghold. In 1821, authorities decided to shut down the highly profitable operations on Galveston Island. Lafitte knew the game was up and agreed to dismantle his organization. Naval officers watched as Lafitte set fire to his headquarters, and the next day, his ship was gone. He then began operating out of Cuba until Cuba banned all forms of sea raiding in 1822.

Ladrones Islands—meaning 'thieves' in Spanish—and the present-day Wanshan Archipelago, which includes Hong Kong and the Leizhou Peninsula, became pirate hotbeds in the South China Sea.

During the period of the imperial Chinese Ming dynasty (1368–1644), foreign trade was prohibited, which led to widespread smuggling and encouraged piracy. Nations such as China, Japan, and Vietnam resorted to black markets, and as each side attempted to suppress its own smugglers, they often overlooked, or even tacitly encouraged, smuggling from the other side.

The Chinese imperial dynasty of the Manchus was initially successful in suppressing piracy, but it resurfaced in the 1760s, particularly around the islands at the mouth of the Canton River, including what would later become Hong Kong. These islands were known as the Ladrones, meaning 'robbers' or 'highwaymen,' a name accurately given by the Portuguese.

There was also a strong measure of cruelty among Chinese pirates, along with a penchant for beheading. A Western captive, John Turner, who was captured and held by Ching Yih, reported inhumane crimes and tortures inflicted on prisoners. After a defeat in Vietnam, Chinese pirates retreated back to China. Rather than competing with each other, seven pirate chiefs formed a confederation in July 1805 by signing an agreement to cooperate. The pirates were divided into six fleets, each with its own colored flag—Red, Black, White, Green, Blue, and Yellow.

A succession of capable pirate leaders commanded the pirates along the southern China coast, the first being Cheng I, the leader of the confederation, who operated from the Leizhou Peninsula in Guangdong and throughout the South China Sea in the late 1700s.

Cheng I commanded the Red Flag fleet, which consisted of 200 junks and 20,000 to 40,000 men, growing to 600 junks by 1807. After his death, his wife, Ching Shi, inherited the fleet and ultimately doubled its size, along with the number of pirates in her command.

When Europeans established empires in the 16th and 17th centuries, the situation worsened. The seas and waterways of China and Southeast Asia were well-established by the local powers. The Europeans, seeking to counter these powerful pirates, eventually formed a coalition with the Chinese navy and succeeded in stamping them out by the 1860s.

Anjediva (modern Anjadip) Island is an Indian island in the Arabian Sea that served as a base for Timoji, a pirate and privateer of the Vijayanagara Empire, who later became an aide to the Portuguese Empire in their conquest of Goa. He capitalized on the ongoing conflict between the warring kingdoms of the Vijayanagara Empire and the Muslim Bahmani Sultanate, which created a constant demand for supplies. Timoji raided Persian horse shipments for the King of Honavar and attacked Kerala merchant fleets for their pepper cargo. By the height of his power, he had amassed over two thousand mercenaries and commanded a fleet of fourteen ships. 

In 1505, Timoji gained the trust of Viceroy Dom Francisco de Almeida by providing key intelligence on the upcoming siege by Calicut forces. In 1510, Timoji persuaded the new governor, Afonso de Albuquerque, to delay his planned conquest of the Red Sea and instead encourage an attack on Goa, expecting the region would be handed over to him after the conquest. The plan to invade Goa was partly driven by Timoji's desire to gain support from Hindu chiefs, who urged him to overthrow the Muslim rule of Adil Shah, as Hindus were being exploited by his subjects. Albuquerque appointed Timoji as Aguazil of Goa, but due to Timoji's lack of compliance, he was stripped of his power. Timoji returned to his pirate activities and was eventually captured after one of his raids. He later died from opium poisoning.

Places to visit

NORTH CAROLIN A MARI TIME MUSEUM, Beaufort, North Carolina

See artefacts from Blackbeard's flagship, Queen Anne's Revenge, which exhibits the history of life at sea and a display of wooden boats.

PIRATES OF NASSAU MUSEUM, Nassau, Bahamas

A museum designed to clear up myths about pirates with tours of nearby pirate sites.