Swashbuckling in the Sister Islands

A siege of pirates and wenches will pillage and plunder the Cayman Islands during the annual Pirates Week National Festival, 7 to 28 November 2015. Now in its 38th year, the near month-long jubilee is considered quintessential among the nation’s cultural events, and showcases and celebrates our history, traditions, food, artisans and musicians.

pirates week (1)

Most events are planned on the largest of the three islands, Grand Cayman, including a mock pirate invasion complete with pirate-like vessels, the capturing of the Governor, a grand fireworks display, a cardboard boat race, dancing in the streets and Heritage Days in each of the Island’s five districts. However, the quieter disposition of Cayman Brac and Little Cayman truly symbolise this year’s event theme: Preserving our past; protecting our future.

Cayman Brac

Legend has it that piracy in the Cayman Islands dates as far back as 1620. The most notorious pirate to invade the Cayman Islands was Edward “Blackbeard” Teach, but the Islands also saw the likes of Neal Walker, otherwise known as “Needle,” both of whom used the Islands as a place to rest, repair their ships and hide their treasures.

pirates week

The deep and often well-hidden caves of Cayman Brac were of particular interest to the pirates and — according to local hearsay — gold, silver and precious jewels are still said to be buried throughout the limestone formations. This makes Cayman Brac the ideal location to kick off the slew of Pirates Week events.

The Cayman Brac Heritage Day is especially known for its commemoration of the “olden days.” Ladies adorned in traditional Caymanian dresses, similar to a plain quadrille frock, serve native dishes like stewed turtle and conch while men walk about in whompas (shoes fashioned from worn car tires and dried silver thatch). Farmers proudly display their season’s best fruits and vegetables and the local crafters show off their works of art. Late in the afternoon, a band of costumed swashbucklers take over the island during the pirates’ “attack,” followed by a colourful and creative float parade.


While you’re in the Brac, trade in your boots for fins and dive the 330-foot-long MV Captain Keith Tibbetts shipwreck near the Buccaneer reef on the Island’s north shore; it is the only Russian Koni class frigate easily dived in the Western Hemisphere. Before heading off to Grand Cayman the following day, pirates and visitors are challenged to a game of dominoes, where the competition is fun but fierce.

Little Cayman

It’s not uncommon to drive the length of this little island without passing a single car, but between the 27th and 28th of November, the 200 residents who inhabit Little Cayman come out for an exciting weekend. Sailing ships and buccaneers dressed in full regalia that would give Jack Sparrow of Pirates of the Caribbean a run for his loot fill the streets and the island’s shores.

Credit: Cayman Compass


On the final Friday of Pirates Week, all feet — and pegs — walk over to McCoy’s Lodge to kick off the festivities. The events climax the following day with a fun and inventive float parade during Little Cayman Heritage Day. It’s a true demonstration of island camaraderie. Local delicacies like fish or salt beef rundown, fried fish with fritters and stewed whelks are often on the menu in Little Cayman as well; grab a to-go container and settle in to watch the fireworks near the Hungry Iguana Restaurant & Bar before working up a sweat at the final fete of Pirates Week.

Watch a video from the 2011 Pirates Week parade in Little Cayman.


Pirates Week Event Highlights

Cayman Brac

November 7     Heritage Day, Float Parade, Pirate Fest Party and Fireworks
November 8     Domino Tournament and Pirates Farewell

Little Cayman

November 27    Kick-Off Dance
November 28    Float Parade, Costume Competition, Pirate’s Dance and Fireworks


Before You Go…

  • Pick up the official Pirates Week T-shirt and your pirate garb — full costumes, beads, eye patches, swords, hooks and hoop earrings — from the Pirates Week Office on Grand Cayman.
  • Book your inter-island flights, accommodations and transportation in advance as availability is limited. Take a little cash with you. Most of the events are free before nightfall, but vendors only accept cash.
  • Sample some of the pirate-inspired Blackbeard’s Spiced Gold Rum and Blackbeard’s Rum Cake.
  • Take a selfie with a friendly buccaneer, so you can remember how much fun you had!

. . .

Published: Skies Magazine, November 2015
Featured Photo: Deep Blue Images

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