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Best swashbuckling places to be a pirate

Published September 19th, 2014

Hey mateys - do you speak fluent buccaneer? If phrases like “Avast me hearties”, “Shiver me timbers” and “Walk the plank” are part of your everyday lingo, you’ll no doubt already be across the fact that today is International Talk Like a Pirate Day. So for landlubbers and scurvy wenches and everyone else in between; grab your galley crew, sing some sea shanties and raise your bottles o’ rum, here’s some of the best swashbuckling places to be a pirate around the world on September 19. Ahoy there!


Yo ho ho and a bottle of rum...



Thar'll be lots of hidden pirate coves ahoy!

Port Royal, Jamaica

Once dubbed the ‘most wicked and sinful city in the world’, Port Royal (mentioned in the Pirates of the Caribbean franchise) attracted pirates from all over to its shores. The Jamaican city was a safe harbour for British and Dutch buccaneers who used the spot to attack and plunder Spanish galleons on the Caribbean trade routes until the late 17th century. However the tide turned with Port Royal passing anti-piracy laws and spots like Gallows Point signalled the end of many a promising pirating career.


Only landlubbers haunt these shores now, me hearties!

Key West, Florida

Plying the same seas, the USA was no stranger to swashbucklers either. The treacherous waters and coral reefs off Key West, not to mention the odd hurricane, claimed many a Spanish galleon and the shipwrecks were duly plundered of their booty. Despite the US Navy protecting Key West from pirates by the early 1800s, wrecking – luring and diverting unsuspecting ships to their demise – was still a thing in the 1830s, making the city the richest in America with a penchant for glitz that lasts to this day.


All the spoils of the Spanish Empire be here.

Cartagena, Colombia

After arriving in 1533, the Spanish were forced to build a walled fortress to protect Cartagena from numerous attacks by British, Dutch and French privateers (sanctioned by their respective countries) and the more lawless pirates throughout the 1600s. Eventually a Spanish officer, Blas de Lezo, who had already lost an arm, a leg and an eye, led a motley crew of 2,500 against 25,000 English soldiers and won. Although he did lose his other leg and died shortly later, he was immortalised in a statue.


The now not-so-ominous Omis coastline.

Omiš, Croatia

Located on the Dalmatia Coast in Croatia, this tiny town was once a dangerous pirates’ lair between the 13th and 15th centuries when Omiš seafaring locals controlled the Adriatic Sea, attacking ships sailing from Venice and Naples and the crusaders as well as charging for passage through these waters. The pirates’ demise eventually came about when the town was defeated by Pope Honorius III and his team of holy crusaders and then eventually sold to Venice.


Guangdong, China

China’s junks in Guangdong were preyed upon by powerful pirate fleets during the early 19th century, and the most notorious was the former Cantonese prostitute and pirate widow Ching Shih (also known as Cheng I Sao) who ruled the South China Sea and commanded over 1,500 vessels and a crew of 100,000. Terrorising from Canton to Macau through extortion, taxes and plundering, Ching Shih eventually retired and got to keep all her loot. And get an upcoming TV show all about her. #winning


Cassandra Laffey

Consumed with unrequited wanderlust, I get my fix in 24/7 cities and hippie retreats. I'm still looking for the ultimate combo of secluded beach and major metropolis, and my happy place is a 5-star hotel room all to myself - sigh.