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Ultimate Road trips: The Pirate Route, Jamaica

From Blackbeard to Calico Jack, find out where to follow in the footsteps of history's most famous pirates.

Jamaica was once the perfect base for pirates. 300 years before it became known for all inclusive, perfect white sandy beaches and crystal clear waters, it was the top choice for a pirate hideaway. The scurvy dogs travelled throughout the Caribbean plundering the new world’s treasure ships and stowing their bounty away.

Thanks to National Geographic (who went to town on road trips all over the world) we’ve been inspired by the Jamaican one to celebrate International Talk Like a Pirate Day (we’ll take any excuse really!) on September 19 every year.

Port Royal As you enter Port Royal you’re greeted with an old sign that says: ‘Where the Buccaneers Drank their Beer.’ That’s the kind of place we want to visit. Port Royal has a trusty Pirate legacy; it was invaded by the undead forces of the infamous Jolly Roger and used as a base by Henry Morgan a Welshman who became known as one of the most successful and ruthless pirates around. It’s also said to have been frequented by the famous swashbuckler Jack Sparrow and Jamaica has made claims as the birthplace of Blackbeard, (but so has Bristol in the UK and Carolina in the US.)

Kingston Head back towards Kingston on your road trip and take a trip to Bob Marley’s former home. Not pirate related, but a must see when you’re in the Jamaica. Further along, about 18 miles on the highway, you’ll find the old capital Spanish Town.  The English pirate, Calico Jack who operated throughout the Caribbean in the ‘golden age of piracy’ was hanged here after his capture in Negril Bay, alongside his two female crew, Mary Read and Anne Bonny. These ladies made the crew by disguising themselves as men. This worked until Read started to develop feelings for Jack himself.

Negril Bay Follow the road around and you’ll find the scene of a great pirate raid. This is where Calico Jack was enjoying a rum fuelled party when Captain Barnet was dispatched to capture him. No doubt his senses were a little dulled and he was caught. Calico Jack was executed and his body was displayed in an iron frame as a warning to other pirates.

Montego Bay The second city of Jamaica is a good place to get the kids involved in a little pirate fun. From there you can hop on a replica galleon, where you’ll be treated to hearty dinner to set you up for an enemy raid. Pirates armed with swords and pistols will jump on deck and a fiery battle will take place!

Ocho Rios A perfect place to finish your pirate road trip. Apart from a simply stunning drive, Ocho Rios is where you’ll find the legendary pirate Henry Morgan’s hideaway. It is said Morgan directed his attacks from behind thick walls. It’s also where the location of British playwright Noel Coward’s estate Firefly. It’s said the room where Coward wrote his compositions – “the room with a view” overlooks a gun slit, “pirate cabin” that hid Morgan from view. Today, Coward’s gravesite stands near a secret tunnel that Morgan used to escape to sea.

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