1. Port Royal

During the “Golden Age of Piracy” in the late 17th and early 18th centuries, Port Royal, Jamaica stood as one of the most popular ports of call for thieves, prostitutes and pirates of every stripe. The small harbor’s association with marauding began in the mid-1600s, when Jamaica’s governors offered it up as a safe haven for pirates in exchange for protection from the Spanish. The buccaneers accepted the deal, and the town soon became a major staging ground for British and French privateers—ship captains commissioned by the Crown to disrupt Spanish shipping in the Caribbean and Atlantic. One of the most famous of these state-sanctioned pirates was Sir Henry Morgan, a Welsh captain who used Port Royal as a base of operations for raids on the Spanish strongholds at Portobello, Cartagena and Panama City.

Port Royal prospered on the back of its pirate economy, and by the 1660s its streets were lined with taverns and brothels eager to cater to the whims of young buccaneers flush with Spanish loot. Contemporary accounts describe a seamy harbor overrun with gambling, prostitution and drink, where hard-living mariners often squandered thousands of Spanish reals in a single night. Even after the age of privateering had ended, the so-called “wickedest city on Earth” continued to serve as a retreat for a new brand of lawless, freelance pirates. But when these raiders began indiscriminately plundering shipping traffic in the Caribbean, Port Royal’s colonial authorities were finally stirred into action. By 1720, the town had begun to clean up its act and its “Gallows Point” became a notorious site for pirate hangings. Among countless others, buccaneers like the ruthless Charles Vane and the flamboyant “Calico” Jack Rackham would eventually meet their end in Port Royal.

2. St. Mary’s Island

Peg-legged pirates and swashbuckling sea captains are usually associated with the Caribbean, but many of the most successful buccaneers plied their trade in the Indian Ocean. Beginning in the late 17th century, well-armed bands of freebooters used the African island of Madagascar as a base of operations for raids on European and Asian shipping. According to pirate legend, some of these pioneering thieves even set up a utopian colony called Libertalia, where they mingled with native women and organized a democratic government. Libertalia is most likely a seafaring myth, but Madagascar was home to several other pirate strongholds, most famously St. Mary’s Island on the northeast coast.

In the 1690s, St. Mary’s boasted a population of around 1,500 and served as a vital supply base for pirates like Captain Kidd, Thomas Tew and Henry Every. As part of an underground shipping arrangement, many St. Mary’s-based buccaneers would attack ships carrying exotic goods from India, and local traders would then sell the booty to crooked merchants in cities like New York and Boston. Some of these raids were among the most lucrative crimes in history. For example, in 1695, Henry Every used a six-ship fleet to attack a treasure ship owned by the Great Mogul of India. Following a bloody fight, he made off with the equivalent of some $200 million in loot.

3. Tortuga

In the early 1600s, the rocky island of Tortuga served as the chief stronghold of a motley group of adventurers, thieves and escaped slaves who preyed on Spanish treasure ships in the Caribbean. These raiders started out as a band of French hunters on nearby Hispaniola (now Haiti), and it was the French word for their method of curing meat, “boucaner,” that inspired their feared nickname: buccaneers. The buccaneers fled Hispaniola for Tortuga around 1630 after the arrival of Spanish settlers, and they soon turned to the lucrative business of piracy. To support their operations, they made Tortuga into a fortified stronghold. Jean le Vasseur, a buccaneer leader who had once worked as a military engineer, even built a 24-gun castle called Fort de Rocher to help guard the island’s harbor.

Tortuga became a prime destination for pirates, attracting men of rough character from as far as England, Holland and Portugal. As more would-be marauders arrived on the island, they organized themselves into a loose fraternity of thieves called the “Brethren of the Coast” and developed their own code of conduct. Many of the Brethren received privateer commissions from England and France, and they proved a thorn in the side of the Spanish, who responded with repeated attacks on Tortuga. The buccaneers later served under Sir Henry Morgan during his famous raids along the Spanish Main, but their influence waned with the end of privateering. While a few continued to prowl the Caribbean for several decades, Tortuga’s buccaneers had all but disappeared by the beginning of the 18th century.

4. Clew Bay

The west coast of Ireland might not seem like prime pirate territory, but in the 16th century the rugged shores of Clew Bay served as the stronghold for of one of history’s most formidable lady corsairs. During a time when Ireland was ruled by dozens of local chieftains, Grace O’Malley defied convention and emerged as the leader of a seafaring clan who controlled the coastlines through intimidation and plunder. From her base of operations at Rockfleet Castle, O’Malley—also known as Granuaile—commanded hundreds of men and some 20 ships in raids on rival clans and merchant ships. She also ran afoul of government officials, who made repeated attempts to curb her activity. When a fleet from Galway besieged her castle in 1574, O’Malley led her pirates in a counterattack and forced the ships into a retreat.

O’Malley was captured in 1577 and spent several months behind bars, but by the 1580s she was once again stalking the seas surrounding Clew Bay. Her hands-on style of leadership earned her a reputation as a ruthless fighter—a popular legend states that she once gunned down a Turkish buccaneer only a day after giving birth—but she also showed a keen understanding of politics. When English colonial authorities eventually captured her son and impounded her ships, O’Malley petitioned the Crown for redress and then set sail for England. During a historic 1593 meeting with Queen Elizabeth I, she personally negotiated her son’s release and even secured the return of her fleet.

5. New Providence

Long before it became a popular stopover for cruise ships and vacationers, the Bahamian island of New Providence was known as a lawless “nest” of pirates—and for good reason. The island sat in the center of the well-traveled trade lanes between Europe and the West Indies, and its capital of Nassau offered a safe harbor for marauders to repair and resupply before setting sail in search of plunder. By the 1710s, New Providence had become a popular gathering place for some of the Caribbean’s roughest customers. Among others, raiders like Blackbeard, Stede Bonnet and Charles Vane were known to haunt its seaside taverns and bars.

Pirate activity in the Bahamas eventually became so rampant that the British government feared for the long-term survival of its colony. In 1718, the Crown dispatched three warships to New Providence along with a new governor—the privateer-turned politician Woodes Rogers. Governor Rogers offered a pardon to any pirates who surrendered—some, like Benjamin Hornigold, even became pirate hunters—but he showed little mercy to those who resisted. In December 1718, he sent a chilling message to unrepentant buccaneers when he executed a band of convicted pirates in Nassau. From then on, New Providence was slowly transformed from a playground for thieves into one of the main headquarters for anti-piracy operations in the Caribbean.

6. Barataria Bay

The swampy islands surrounding Barataria Bay, Louisiana, once served as a sanctuary and safe harbor for the famed pirate-turned-patriot Jean Laffite. In the early 19th century, Laffite and his brother Pierre led a syndicate of thieves who terrorized shipping in the Gulf of Mexico. Working as privateers for the upstart Republic of Cartagena, Laffite’s buccaneers plundered Spanish merchant vessels and then smuggled stolen goods and slaves into New Orleans. By the 1810s, their illegal colony at Barataria Bay had grown into one of the busiest black market ports in all of North America. Between 500 and 1,000 marauders frequented the area, and more than a dozen pirate ships regularly occupied its harbor.

In 1814, Laffite famously interrupted his pirate activity to play an unlikely role in the War of 1812. After receiving an offer from the British—who hoped to use Barataria as a point of access to New Orleans—Laffite instead offered his services to the United States in exchange for clemency for his past misdeeds. Laffite and his followers went on to serve with distinction in the Battle of New Orleans under future President Andrew Jackson, and he was rewarded with a full pardon. But despite winning a clean slate, Laffite would not stay away from a life of crime for long. He later led his men to Texas and formed yet another pirate haven on Galveston Island.

HISTORY Vault: True Caribbean Pirates

Blackbeard. Anne Bonny. Henry Jennings. Calico Jack. Henry Morgan. Black Bart Roberts. Examine the Golden Age of Piracy and the true stories of these infamous pirates, how they operated, and their successes and failures in this dark and deadly profession.