Real Pirates of the Caribbean

Adventures in Trinidad and Tobago tourism...

The real pirates of the Caribbean found Trinidad and nearby Tobago excellent harbors from which to attack heavily laden, and often defenseless, merchant ships leaving the Spanish Main.

 City of Gold 

For almost 300 years after Columbus, Trinidad was little more than a launching point for expeditions to fabled El Dorado, which at the time was thought to lie somewhere between the great Orinoco and Amazon rivers, and where it was believed the precious metal was so abundant that the king painted his body each morning in gold dust.

 Backwater Colony 

With such a rich prize pulling Conquistadors ever deeper into the South America continent there was little incentive for the Spanish Crown to support a colony in Trinidad, whose only commodity was a seemingly inexhaustible supply of Carib Indian slaves to feed the pearl diving industry on the island of Margarita.

As a result Trinidad was a backwater during much of Spanish rule, and Port-of-Spain a wide-open port to ships and seaman of every nation. The Spanish Governors lacking a strongly fortified harbor, and possessing only a laughably small and under-funded garrison of Spanish troops, could do little more than accept lucrative bribes from English, French and Dutch smugglers and privateers.

 The Boca Islands 

Trinidad's Boca Islands, with their numerous small natural harbors provided excellent cover from behind which the real pirates of the Caribbean could pounce upon unsuspecting merchant vessels entering and exiting the Dragon's Mouth and the Gulf of Paria.

Winn's Bay on the south coast of Gaspar Grande (Gasparee) was originally known as Corsair's Bay. This hidden bay must have made the perfect hiding place from which to ambush shipping entering and exiting Port-of-Spain. There is also a persistent legend that real pirates of the Caribbean treasure lays buried, within the Gasparee Caves.

Tobago's most northerly beach, Pirates Bay near Charlotteville, is another of the many ideal natural harbors that the real pirates of the Caribbean are believed to have used as home bases form which to attack Spanish and Portuguese shipping lanes.

 Real Pirates of the Caribbean 

What to one country were real pirates of the Caribbean were to another heroes, heroines and great warriors.

For example, while Sir Walter Raleigh is to English history an adventurer, to the Spanish he was the "Grande Pirate".

Pirates like Walter Raleigh often started their trade as agents of European Royalty; others had private financial arrangements with the governors of maritime North American states or Caribbean islands, who offered refuge, and a safe place to maintain their ships, for a price.

One of the reasons given for Sir Ralph Abercromby's attack and subsequent capture of Trinidad and Port-of-Spain from the Spanish was that, "it was the source of great mischief to the British Islands, being a shelter for privateers who annoy trade and afford asylum to bad people of every description."

 Edward Teach, Blackbeard 

The most infamous Corsair of all time, Captain Edward Teach (Blackbeard), is known to have harassed shipping in the Gulf of Paria during 1716, and will have very likely used many Boca island bays as convenient anchorage during his adventures in Trinidad and Tobago.

Blackbeard was one of the most interesting pirates and would have made a great PR man. He purposely cultivated his reputation, doing everything possible to enhance his image, even going so far as to place slow matches under his hat when he went into battle to terrify his opponents.

However, while Blackbeard was one of the most fared Caribbean Pirates, whose crew at one time numbered over 300, and who is believed to have captured some 45 ships, there is no evidence that he every killed anyone who was not trying to kill him. In 1717 Blackbeard rejected a Queen’s pardon, only to be killed 1 year later in a bloody fight to the death with the Royal Navy.

 Distant Blood Relative 

Another real Caribbean pirate who likely sailed Trinidad and Tobago waters looking for plunder was Captain "Red Legs" Greaves. Distantly related to one of my husband’s ancestors, Red Legs was the Robin Hood of Pirates, who distinguished himself for his humanity and morality, by rewriting the pirate code to ensure that women were treated properly, prisoners were not tortured, and the poor were not robbed.

Captain "Red Legs" Greaves greatest prize was the island of Margarita, just west of Trinidad along the South American coast, where he captured a huge booty of pearls and gold. True to form his men did not plunder the town.

He was later captured, but was one of the few people to escape alive from "goal" (jail) during the earthquake that submerged Port Royal in Jamaica. Reputedly he ended his days quietly as a planter in the Lesser Antilles, where he became known as a philanthropist.

 Famous Women Pirates 

While there is no conclusive evidence, it's highly probable that the most famous women pirates of the Caribbean also plied the seas around Trinidad and Tobago seeking rich prizes.

Anne Bonny and Mary Read, female adventurers with stories worthy of a major Hollywood blockbuster, secretly lived as men during an age when most women were confined to the home.

But these women were the equals of any man with the sword, and when captured they were the most courageous of their crew. Later Anne Bonny would proclaiming to Calico Jack, her lover and the captain of the crew, "if you had fought like a man, you would not now be hanged like dog." Both Anne Bonny and Mary Read were spared the noose when it was discovered that they were pregnant.

 Signs of a Pirate Past 

Signs of the real Pirates of the Caribbean and the days of sail linger even 250 years later, if you know where to look...

As a child my husband often found pipe heads on the beaches around Scotland Bay and Chacachacare, the fine white clay pipes, which were used from the 1500s to the late 1800s, broken pipes heads discarded by sailors when sailing ships moored in these protected bays down the islands.