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All You Need to Know About Pirates Week in Cayman Islands

November 01 2017
Pirates Week in the Cayman Islands

Old-School pirates aren’t extinct! They are there, and invade the Cayman Islands once a year

Pirates are a dangerous lot – notorious for their brash mannerisms, filthy habits and bloodlust. Movies like the ‘Pirates of the Caribbean’ didn’t do much to portray them in a good way; except for the affable Captain Jack Sparrow, there is not much to like about them.

However, readers familiar with the Pirates Week Festival would beg to differ. Every year, during the month of November, the pirates take a break from terrorising the seas, and instead, prefer to make merriment in the Cayman Islands for a full 5 days. Not only that, they also choose to make everyone on these isles walk the plank to fun and entertainment (tourists included).

This year will mark 40 years of the Island’s longest running and most popular national event. This year there is a major change as the festival has been restructured into a 5-day affair from the earlier 10. Though this doesn’t mean that the fun will be any lesser. Expect delicious local cuisines, Caribbean music, competition, street dances, shimmering fireworks, vibrant parades and even a pirate invasion!


Proceedings normally begin with a steel pan competition and a kick-off party. The evening brings more cheer with a brilliant fireworks display amid the cool ocean breeze, and will surely bring delight to people of all age groups. The next day, even more activities are planned that are guaranteed to lift your mood.

The second day is when the Festival Queen is crowned. A title that is hotly contested by women over 16 years of age. This is followed by the opening Street Dance (the first of many), that are attended by thousands of people; making the streets come alive.

After exhausting their energy on the dance floor, that are the streets of George Town, the crowds can head to the Food Festival. There’s no better place to be in the Caribbean, with local delicacies such as stewed conch, stewed whelks, turtle stew and even dessert like trash corn to dig in to.

The Invasion

A mock pirate invasion is carried out from the sea. Two ships, made to look the part, and loaded with pirates, come in from the sea and drop anchor at George Town Harbour. The pirates jump off the ship, fight off some guards and capture the Governor of the Cayman Islands (Earlier, the real Governor used to take part but now an actor carries out this role).

Also known as the “landing”, this act presents a great opportunity for everyone to dress up as pirates. The pirates then “invade” the island and a parade ensues along Harbour Drive, with themed floats, walking groups with colourful costumes, live music and much more. It is quite a spectacle to watch them on the streets; families just love this part.

Heritage Day

This year marks the 40th edition of the festival and for the first time, the Heritage Days won’t be spread over a few days all over the island, but will happen in a span of one day in George Town itself. This move is made to provide equal opportunities to all districts to showcase their unique identity, and celebrate their diversity as one.

For the festival goers, it is a day to sample how life in the island was during old times. It is also the best place to sample authentic Cayman cuisine and buy original souvenirs. For those who are looking for traditional Cayman culture and art, these Heritage Days are the place to be.

All said and done, the Pirates Week festival is the best time to visit the beautiful Cayman Islands in the pursuit of unbridled fun. All the attractions and eager participation from the locals make this an event truly worth waiting for. So, don’t forget to tick this off your travel list soon, and when you do, set off do so with a travel insurance policy that ensures you have the maximum fun possible without any worries.

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