Shiver me timbers, the pirates are back in town

Pirates Week kicks off Thursday for 15 days of family-friendly, swashbuckling fun.  

The 15-day event is the islands’ longest and most successful festival, which is celebrated across all three islands with a host of events, heritage days, musical concerts, parades and fun-hearted competitions. 

The event was started in 1977 by Jim Bodden, then minister of tourism, to bolster tourism numbers during the islands’ slow season. While the week wasn’t intended to specifically celebrate actual pirate history, buccaneers did use Cayman as a base for restocking supplies during the 18th century. Indeed, famous pirates such as Blackbeard and Henry Morgan are said to have landed in Cayman, and it is believed by many that their treasure may still be buried in one of the islands’ undiscovered caves.  

Now in its 37th year, Pirates Week has grown to encompass more than 30 free events and is now the islands’ biggest festival, attracting thousands of tourists each year, including the Seattle Seafair Pirates, an established pirate troupe who are always guaranteed to entertain the crowds.  

Weekender rounds up some of the must attend events that are always a favorite with visitors and residents alike: 

Cayman Brac Pirates Landing 

The pirates descend on Cayman Brac with the Jolly Roger pirate evasion and float parade at Scott’s Dock, 4-6 p.m. followed by the Pirates Fest Party, from 9 p.m. – midnight.  

Pirates Week Kick-Off Party, The Wharf 

The Pirates Week festivities officially kick off on Grand Cayman with live music, food and drink. Be sure to don your best pirate garb. 9 p.m. 

Food festival, costume competition, fireworks and street dance, George Town Harbour 

Enjoy a food festival from 5 p.m., featuring a host of vendors selling local specialities. Children’s pirate costume competition from 7 p.m., Miss Festival Queen competition from 7:45 p.m., fireworks at 8:30 p.m., and a street dance from 9 p.m. to 2 a.m. with Kes the Band from Trinidad.  

Landing pageant and float parade, food festival, street dance and ‘Teen Up’ in George Town Harbour 

One of the main events and highlights of Pirates Week, you don’t want to miss it. Starting at 3 p.m., boats decked out in full pirate regalia, descend on George Town Harbor and unload their motley crew of pirates and buccaneers who “take” George Town. The float parade follows with thousands of spectators lining the streets to take in the show. The food festival is next, with local vendors offering delicious Caymanian dishes – from stew turtle to curried goat. The street dance kicks off at 7 p.m. featuring Mighty Gabby from Barbados and Jamaican band Fab 5. Teenagers can head to the Teen Up street dance on Goring Avenue from 8 p.m.-midnight.  

Children’s Fun Fair, Pedro Castle 

Little ones and pirates in training will enjoy this kid-friendly event from noon to 4 p.m. with plenty to keep everyone entertained. 

Heritage Days 

Heritage Days are a great way to soak up some of Cayman’s unique culture. Each district hosts their own event throughout the week highlighting various aspects of each area’s distinct culture and traditions. Visitors can enjoy local arts, crafts and traditional foods, with many recipes having been handed down throughout the generations. 

Cardboard Boat Race 

The Cardboard Boat Race has grown to become a firm favorite in Cayman. The action-packed water event sees teams competing to see who can stay afloat long enough to complete a circuit around Hog Sty Bay in a boat made entirely of cardboard, duct tape and glue. Over the years there have been some fantastic creations – whether they can stay afloat is quite another matter. The race starts at 4:15 p.m. Be sure to get there early to ensure a good vantage spot to enjoy the race.  

Sentencing of the pirates, fireworks and street dance 

Pirates Week wraps up in a blaze of glory with the sentencing of the pirates, a spectacular fireworks show and the festival’s final street dance. The fun kick soff at 7:40 p.m. with the sentencing of the pirates.  

Little Cayman Pirates Celebrations 

Little Cayman hosts its own Pirates Week celebrations, with a kick-off dance at McCoy’s Lodge from 9 p.m. until late on the 21st. The following day festivities continue with the float parade starting at Head O Bay from 3 p.m. Then, starting at 5 p.m. enjoy a costume competition, pirate’s dance and fireworks show at the Hungry Iguana.  

For a full listing of events, visit All events are free


A young pirate in training enjoys last year’s Family Fun Day during Pirates Week. – Photos: Chris Court


Aarrrrr, could it be Jack Sparrow?


Pirates will entertain the crowds this Pirates Week


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