Grand Cayman, North America, The Cayman Islands, Trip Reviews

Pirate’s Week in Grand Cayman

17/12/2013 by .
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Late afternoon in George Town and I’m wearing an eye patch and sweating buckets. Not surprising really considering I’m halfway through a 5K run. That’s what happens during Pirate’s week in Grand Cayman. I say a 5K run, it’s more like a 5K stroll to be honest, considering the humidity is 95%. But this run is the curtain raiser to the annual Pirate’s Week festival on Grand Cayman, a time for much swashbuckling merriment complete with treasure hunts, carnivals and plenty of late night music, fireworks and of course colourful pirate costumes, mayhem and merrimentCayman Islands 091

Pirate’s Week was the brain child of Jim Bodden in 1977 when the then Tourist Minister happened upon the genius idea of sprucing up the month of November, a traditional slow season on the island. Locals are quick to point out of course this is not in any way celebrating actual piracy, (even though let’s face it, we are in the Caribbean ) more a celebration of the cultural side of Cayman life, albeit mixed up with authentic looking Captain Jack Sparrows and ample mugs of rum.

From humble beginnings, Pirate’s Week has evolved into an eleven day festival that does indeed combine much of Cayman culture with Pirate fun. Who can resist a subterranean treasure hunt for example? Divers and snorkelers romping around the coral laden waters of the North Sound hunting for silver pieces of eight, each one earning the finder a local prize. Or the Landing Pageant, where a band of motley pirates land their galleon in the harbour and “kidnap” the Governor – a mock battle full of loud cannon fire and cutlass rattling. And my particular favourite, the cardboard boat regatta at Hog Sty Bay where all manner of homemade cardboard boats compete to see who can stay afloat and get to the finish line.Cayman Islands 094

Once night falls a different vibe ensues. Outdoor stages come alive with music, street parties swing into action, more rum flows  and restaurants and bars are buzzing.

I check out The Wharf, reputed to be the place to party during Pirate’s Week and find it all very sensible; well dressed diners enjoying some fine food and a reggae band filling in some background standards. A quiet Thursday night out. Then, with firecrackers and banshee howls the pirates descend on us from the water’s edge, all bandanas, boots, buckle and swash. That kicks it off. The Wharf transforms from jolly dinner to Johnny Depp and all’s well with the world.Cayman Islands 233

It seems Pirate’s Week does as much for the locals as it does for tourists. A chance to let hair down on both sides, and I must admit a growing fondness on my part for thigh high leather boots, but that’s another story. For now I’ll just stick with the eye patch.

Pirate’s Week takes place each November on Grand Cayman and Little Cayman.

Getting there:

Caribtours (020 7751 0660: offers 7 nights from £1,978 per person, based on 2 adults sharing an Island View Room on Room Only. Includes return scheduled flights and private transfers.

British Airways operates a service from Heathrow to Grand Cayman four times a week. Why not upgrade to World Traveller Plus and get additional legroom, wider seats, priority boarding and extra baggage allowance.The lead-in fare is from £779.75 including taxes/fees/carrier charges.

To book or for more information visit or call 0844 4930787.

Main image: Pirates Week parade on Grand Cayman (c) Andy Mossack





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