I Was The Last Pirate in Montego Bay

  I was the last pirate to visit Montego Bay, Jamaica. My kindred seafarers roamed the coast centuries ago. I was there in 2009. You could say that some things have changed since then. Instead of drinking at some colonial Spanish tavern, I was downing rum at Jimmy Buffet’s Margaritaville. Hundreds of natives were trying to sell me pot instead of hog lard. Audio speakers blared Sean Paul rather than the sea shanties of old.


I didn’t do anything remarkable in Jamaica (other than win a bottle of Appleton rum at a resort contest!). Jamaica is a very remarkable place, however. The beaches are pristine, the culture has a very unique aesthetic, and the history is rich.

Calico Jack

In 1655, William Penn, under the brutal rule of Oliver Cromwell, violently seized Jamaica from Spanish settlers. This set off a war and resulted in British dominance over the island for over 300 years. This British conquest also led into the Golden Age of Pirates. One of the most famous duos: Calico Jack Packham and Anne Bonny.

Calico Jack brought this flag into popularity:


It is a symbol of cruelty, fun, corruption, fantasy, thievery, adventure, and barbarity. Calico Jack Rackham enjoyed all of these things. A General History of the Pyrates (Dover Maritime) details the beginning of his career:

“The 24th of November 1718, was the first Day of his Command, and his first Cruize was among the Caribbee Islands, where he took and plunder’d several Vessels..”

Do you remember the scene in the first Pirates of the Caribbean where they raid a ship looking for Jack Sparrow, he sneaks onto the English boat, and sails away with complete ease? This was partially based on a real Calico Jack encounter in Cuba (scroll to: “Rackham Steals A Sloop”). The story goes that Jack Rackham and his crew snuck onto a prized sloop that the Spaniards seized from the English. While doing this, Rackham cleverly used his own ship as a decoy. The English raided the decoy, and Rackham sailed off.

Calico Jack sailed the waters of Cuba, the Bahamas, and Kingston, Jamaica. He is notorious for seizing the Kingston merchant ship out of Port Royal, Jamaica. The Brits eventually caught up with him and took back the Kingston, however. As countless numbers of pirates came in and out of Port Royal, I’m sure the English were often on their guard. Calico Jack wasn’t the only badass to frequent this legendary town.

The “Wickedest City on Earth”


Port Royal, right outside of Kingston, earned the aforementioned nickname with the help of dirty, depraved pirates. One in every four buildings was reportedly a brothel. When I visited Jamaica, the brothel came to you, but that’s another story.

Contrary to the misconception that rum was the pirate drink of choice (it wasn’t until later in the 1600’s they began to imbibe), they were often winos. Passersby in the street were expected to drink from wine set outside. My experience, on the other hand, consisted more of a mandatory Red Stripe every time I passed this beautiful pool:


The pirates loved their wine, however, and their treasured stashes were mostly plunder from Spanish cargo.

I imagine old Port Royal to be like scenes from the TV series Black Sails. Orgies, gold, gratuitous violence. But it’s hard to say, because a chunk of the city is now under sea. Being the buccaneer version of Gomorrah, Port Royal came to its tragic end with a massive tsunami and earthquake in 1692.

Montego Bay

Like the rest of Jamaica, Montego Bay has its history of English dominance, piracy, rum-drinking, and Patois slang. As I sprawled out on the beach, puffing a cigar and admiring the indescribable beauty, I asked one of the locals a question I had for a long time.

“What does bumbaclot translate to?”

The answer is vulgar, and if you really want to know, Google it. I finished my cigar, waded through the ocean, and dreamed of what miraculous destiny would come upon me later in life. Eight years later, as I write this, I’m still a pirate.

Here’s proof:


I shared many conversations with the Jamaicans about Usain Bolt, Rastafarianism, their independence, the land they know and love. Jamaicans are extremely prideful. They not only sell you handmade products, but will talk at length about the meanings and relevance behind their art. Sure, crime and corruption is high, but the people keep to one simple mantra: no problem. Easily one of the top 10 Caribbean destinations, Montego Bay is the place for a laid back pirate-wannabe.

Note: You may click the Calico Jack flag above to be linked to a pretty sweet pirate shirt.

A special shout out to Neville Spence’s Facebook group for the support.

3 thoughts on “I Was The Last Pirate in Montego Bay

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