Tobago Stories

Tobago possesses a fascination that has drawn people to it for close upon five hundred years. In myth and in recorded history, in stories told and in very old books, one finds all sorts of curious references.

Historian Jack Archibald said to me that old Mr. Bullbrook, past curator of the Royal Victoria Institute, told him that one such myth had to do with Caribs and how they maintained the notion that Tobago was the ‘earthly paradise’ of their people. In their belief system, the island contained a ‘porthole’ to heaven. When approaching the end of their lives, Caribs would leave other islands to the north and even as far away as ‘down the main’. They would turn the bows of their long canoes to beach them on some shingled shore in Tobago, journey into the mountains of the island’s central ridge and find the ’porthole to paradise’.

The island is about 26 miles long and 7.5 miles wide, with an approximate area of 116 square miles. It is situated about eleven degrees fifteen minutes north of the equator and sixty degrees forty minutes west longitude, being approximately twenty miles to the north east of the island of Kairi, now known as Trinidad.

In the late 15th century, the 1490s, it has been suggested that Tobago possessed a population of tribal people that may have numbered about 1,500. Their villages were situated mainly in the western and low lying areas.

Centuries before a great migration process had commenced, a warlike people - today referred to as Caribs - came from that vast and ancient wilderness on the mainland of South America. They came from the Amazon basin, followed the mighty Humboldt current, and drove their corials towards the long blue mountains on the furthest horizon. They settled on some of the Caribbean islands in great strength. Their descendants were essentially Carib, though their genes became mixed with that of the women of other Amerindian tribes who had been captured and taken as wives during the years of migration.

During those years in faraway Europe men were nurturing dreams of ‘islands in the furthest west’ for generations. One of them was Sir Thomas More (1478 - 1535), the great English statesman and scholar, who in his steadfast refusal to recognise any other head of the church than the pope, was beheaded by King Henry VIII. More expressed these dreams of another world in his Latin book ‘Utopia’ (written in 1516, translated into English in 1556). Other tales that made the rounds in Europe in those years were the ones of the St. Brendens islands, and of islands that were sometimes found by chance and then lost again. Europeans dreamed of warm places where spices could be had, spices and hot peppers to relieve the boredom of their food. Tabaco - the name given by the Caribs to their long-stemmed pipes - ‘cohiba’, the leafy plant, was soon known as ‘tobacco’ and also lent its name to the island of Tobago.

Tobago was presented to Jacobus, Duke of Courland, by his godfather James Stewart, King of Scotland and England. A dubious gift, however. It happened perhaps in 1651 that Duke Jacobus had come to an amicable arrangement with the Earl of Warwick, whereby he had purchased the letters patent that included Tobago in their grant in the belief that possession of such would strengthen his right to settle the island.

The Dutch, wresting the Low Countries from their Spanish overlords, also made for this magical island, and had in fact stumbled upon it long before the Courlanders. A Dutch man called Jan de Moor came to Tobago, after whom ‘Jan de Moor Bay’ was named, which was eventually corrupted into ‘Man of War Bay’.

Jan de Moor was a merchant and a member of the State Council of Holland. A rich man, he financed some of the earlier Dutch attempts at settlement in the Amazon and on the Guyanese coast in the years 1613 - 1614. He did business with the Courteen family, and Anglo-Dutch trading firm who maintained a settlement at Kykoveral on the Essequibo and who had settled Barbados on their own account.

Jan de Moor had this too in mind for Tobago and made two attempts. Both failed, the last in 1633, when he sent his people under an English man named Gayner. They set up themselves at Toco, Trinidad, and then in Tobago. This came to nought as the energetic Captain Diego Lopez de Escobar, the governor, routed the would-be colonists.

Almost too numerous to mention are the battles for Tobago. For over 150 years, the Courlanders transported Africans to Tobago to grow spices and tobacco. Spain, who reserved first claim to the island, challenged them. There was cotton in quantity, and eventually sugar cane was introduced. The Courlanders, however, were eventually driven off by the Dutch, who faced a new foe, the French, who in turn were challenged by the English. Tobago was a major arena in the European wars!

Sea rovers or privateers, sometimes sailing from the North American colonies, who were making a dash for freedom from British rule, sometimes struck Tobago as well. In March 1777, at Queen’s Bay, a “private schooner came up to the bay under the cover of darkness and sent armed boats to seize whatever they could find. In this case, the raid was successful, and the surprise complete. Without meeting any resistance, they cut out a sloop belonging to a Tobago planter named Hackett, loaded with goods and having on board several sailor negroes. They captured another belonging to the Campbells, loaded with 30 hogsheads of sugar from the Betsy’s Hope Estate, various other goods with six prime sailor negroes of great value.” (K.S. Wise)

In a compromise, Tobago was declared a desert island. Eveyone was meant to leave it. But a remnant population lingered on, made up of ex-slaves, intermingled with the black Caribs who had come from St. Vincent, and Europeans who had somehow missed their returning boats. There is the story of a catholic priest who was sighted by a ship that had dropped anchor in Great Courland Bay. He refused to be ‘rescued’ and the ship sailed away. That was perhaps in the early 18th century; noone seems to know for sure.

Pirates on Tobago

Men dressed themselves in skins and lived in carat-roofed lean-tos. There was no paper and no woven materials for clothes. The gunpowder had become solid in the barrelds; the old muskets were now used for structural purposes. English writer Daniel Defoe (1660 - 1731) used this scenario for an adventurer’s tale, ‘Robinson Crusoe’, which was first published in 1719.

Pirates discovered Tobago, giving the name to ‘Pirates’ Bay’. Many pirate stories are told concerning their depredations on or in the waters off Tobago.

One of them, Captain Anstis, came to the rescue of another equally infamous one by the name of Fenn, whose ship had run aground. Anstis took his ship to Tobago, successfully escaping His Majesty’s ships of war, the ‘Hector’ and the ‘Adventure’. In April 1723, Anstis and Fenn found a quiet spot in Man-o-War Bay, in which there was a sandy cove now called ‘Pirates’ Bay’. Just when all the guns and stores had been landed and the ship, the ‘Good Fortune’, had been put ashore and careened (that is layed over on its side), ill luck would have it that H.M.S. ‘Winchelsea’ was sighted far out at sea. Now began the race for life between the pirates and the navy, and with great effort the former were just able to get their ship afloat and escape under the cover of night before the gunship could block the bay.

The pirates had, however, to abandon their guns, cannons and stores. They also left Captains Anstis and Fenn and nine others on Tobago, who fled into the woods. When the ‘Winchelsea’s Captain, Mr. Orme, realised that he had lost the main prize, he determined to search Tobago from end to end and at least secure those who had been left. Dragging themselves through the woords, living on nuts and lizards, afraid to remain in one place, afraid to light a fire or shoot game, the pirates lost courage. Blaming Captain Anstis for their misfortune, they chopped him to death as he lay asleep.

Shortly after, they were captured by the British sailors. No doubt the Caribs had betrayed them. One of the pirates, Will Ingram, was hanged right there in the forest. He was described as a “very hard and resolute man”, while Captain Fenn was taken to Antigua and hung in irons on Rat Island. Five of his fellows were hung at high water mark and the sixth was granted a reprieve.