Piracy of the Caribbean III: Now a Trilogy – 2021

Much like our trip to the Caribbean over the next few years, the history of the Caribbean islands are not only heard in the land, but at sea as well. Piracy is not just the theme of our adventure, but it was a way of life for hundreds of years because of the men and women who fought for the law, and other law breakers, to be able to live their lives the way they wanted to, as well as in order to line their pockets with the appropriate amount of coins. Today we are going to take a look at a legendary Pirate of the high seas, and to highlight some of the great stories!

Samuel Bellamy, better known by the moniker of “Black Sam” Bellamy, was an English pirate who roamed the seas in the early 18th century. Bellamy was born in 1689 to parents Stephen and Elizabeth in Devonshire, England. The youngest of six children he took up sailing very early in his life and by the time he was in his teenage years he had joined the Royal Navy and fought in many conflicts.

He had a wild affair with a woman by the name of Maria Hallett, sometimes called the ‘Witch of Wellfleet’ for the belief that she used witchcraft to curse Bellamy when he did not return to her in a prompt fashion. Bellamy turned to a life of piracy and was very effective in the year he was active, even crossing paths with the man who would one day become known as Blackbeard! Bellamy would go on to capture or sink 53 ships in that short span and he became feared throughout the New World for his brilliant tactics and the ruthlessness that he managed to display.

Just two months after acquiring the Whydah, a massive ship which was the largest pirate ship up until that point, it crashed off the coast of Massachusetts and claimed Bellamy’s life. Much of Bellamy’s fame came after his death, as it was calculated by Forbes that Bellamy was actually the richest pirate of all time, being worth over 130 million dollars at the time of his death when accounting for inflation.

Captain William Kidd was a Scottish sailor who sailed in the 17th century. He was tried and executed for piracy after returning from a trip that had sent him to the Indian Ocean. Many historians now believe that Kidd’s piracy charges were actually trumped up and that he was a mere privateer.

What has contributed to the great myth about the man though is the belief that he left buried treasure behind to be found. This belief has penetrated popular culture for a long time, earning mentions in Edgar Allan Poe’s “The Gold-Bug” and perhaps most famously in Robert Louis Stevenson’s Treasure Island.


Have you decided the pirate’s life is for you? Fantastic! We are proud to be hosting the Black Pearl Ball, which is our welcome aboard Masquerade party!We want you looking like a proper, landowning pirate of course! Can’t have you show up in rags, what would the ‘Gentleman Pirate’ think of that!? For some good ideas for pirate outfits as well as accessories, go here. And for all of the details about our Drag Stars at Sea: Pirates of the Caribbean, go here.

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