Arrrrhhh me mateys, it's

Shiver me timbers, Cayman’s annual Pirates Week Festival is just around the corner! 

The multi-faceted festival, which spans all three islands, sees a host of swashbuckling pirates descend on Cayman’s shores, offering a week of family-friendly events. 

It actually officially starts on Friday, Nov. 6 on Cayman Brac and ends on Saturday, Nov. 28 on Little Cayman, so perhaps it should be called “Pirates Month”! 

On Grand Cayman, the swashbuckling fun gets under way with a steel pan competition and kick-off party on Thursday, Nov. 12 at The Wharf, followed by the opening Street Dance, Food Festival and fireworks show on Friday, Nov. 13. 

Popular annual events include the Heritage Days, Miss Festival Queen Competition, Food Festival, Pirates Week 5K Run, mock pirate invasion and sentencing of the pirates, Cardboard Boat Race and fireworks display, to name just a few.  

Attended by thousands of visitors and locals alike, this year organizers are adding three new events; the Pirates Week Charity Golf Tournament; the Pirates Pooch Parade; and the Illumination Night Parade.  

“Pirates Week is the most significant event on the Cayman Islands’ social and cultural calendar,” Melanie McField, executive director of the Pirates Week Festival said. “It is one of the few participatory festivals on island where you are more than just a spectator. Not to mention, it is one of the few times a year that people truly indulge in our unique traditional Caymanian cuisine and experience the pride of Cayman.” 


Started by the Executive Council Member for Tourism, Jim Bodden in 1977, Pirates Week was originally created to help bolster tourism in what is traditionally a slow time of year. The festival has grown from a single pirate’s street party into a spectacular range of events. 

Although pirates were long gone when Cayman’s ancestors settled, Pirates Week seeks to capture the excitement and adventure of the islands buccaneering past. 

The only event of its kind in Cayman, Pirates Week has made a firm name for itself as one of the highlights of the Caribbean calendar. In addition it is an ideal time for tourists, residents and locals alike to learn more about this particular aspect of Cayman’s rich culture and historic heritage, thanks to pre-organized heritage days. 

Classic events 

The weekends on either end of Pirates Week mainly concentrate on George Town, bringing pageantry and music to the islands’ capital. If you don’t have time to participate in all the events, make sure you at least manage to fit in some of the most popular ones. 

Friday, Nov. 13 – Fireworks and Street Dance 

Get the family to the waterfront for the incredible fireworks display that lights up the harbour every year. It’s a truly spectacular show guaranteed to impress all ages and always features a huge finale of light, color and sound. 

Once the fireworks are done, head to the food stalls for some delicious local cuisine and dance the night away to live bands. It’s a great way to burn all those calories. 

The fireworks start at 8:30 p.m. 

Saturday, Nov. 14 – Landing Pageant and Float Parade 

If there was any question of whether the pirates were coming or not, all doubts will be put to rest when they land in Hog Sty Bay and “take” the town at 3 p.m. Buccaneers and wenches swarm the streets to the delight of residents and visitors, followed by a float parade featuring some very inventive and creative designs. 

Again, there will be music, food and drink leading into the night so everyone can celebrate another successful invasion. 

Sunday, Nov. 15 – Underwater Treasure Hunt/Children’s Fun Fair Day 

Head to Divetech in West Bay to try your luck finding underwater treasure. There will be a mess o’ coins strewn beneath the waves, and each one is associated with a prize. Gather as many as you can so you can boast about your booty. The hunt begins at 1 p.m. 

Families should make a day of it at Pedro St. James, where the Children’s Fun Fair kicks off at noon. The kids can blow off some steam while the parents relax and enjoy the festivities. 

Saturday, Nov. 21 – Cardboard Boat Race 

This relatively new event has become one of the most popular on the schedule for both participants and onlookers. Crafts of all shapes and sizes, created from a very short list of not terribly waterproof materials, hit the water in a race that often ends in lots of laughter and sinking vessels. 

It’s extraordinary to see the imaginative designs before they succumb to the sea, so get there early for a good vantage point. Boats are on display from 11:30 a.m. 

New events 

Some new items have been added to the roster, so take look to see which ones float your (cardboard) boat. 

Wednesday, Nov. 18 – Golf Tournament 

The golf tournament is an all-inclusive half-day event scheduled for Wednesday, Nov. 18 at the North Sound Golf Club, with tee off at 1 p.m. 

“This unique event is perfect for a corporate outing or just a simple golf get-away,” McField said. “The golf tournament was created with the mission to partner with various charities to raise monies that provide medical services, educational programs, lifesaving equipment, and fundraising opportunities to better the lives in the communities across the Cayman Islands,” McField added. 

“The Golf Tournament with the help of its sponsors, celebrity pirates, and every person that participates in the event, hopes to raise funds with part proceeds will go toward the chosen charity, Alzheimer’s and Dementia Association of the Cayman Islands.” 

Saturday, Nov. 21 – Pirates Pooch Parade 

The first annual Pirate Pooch Parade aims to celebrate Cayman’s four-legged friends, with funds raised going to the Cayman Islands Humane Society.  

The pooch parade will take place on Harbour Drive (next to the main stage) on Saturday, Nov. 21 at 9 a.m. 

Admission is $25, which includes a free T-shirt. Prizes include People’s Choice, Most Photogenic Pooch and King and Queen Pirates Weeks Pooch. There will also be a raffle, grog and grub to hand.  


Saturday, Nov. 21 – Illumination Night Parade 

Dubbed as Cayman’s brightest and most vibrant parade by festival organizers, the Illumination Night Parade is set to feature floats, dance troops, acrobats, bands, pirates and much more! The parade takes place on Saturday, Nov. 21 on Harbour Drive, 7 p.m. 

“This is one event you do not want to miss,” McField said. 

For a full listing of events visit

Some of the pre-landing entertainment has been pretty high flying in the past. – Photo: Chris Court


This young wench keeps her parrot close at all times.


Arrrrhhh the wenches like some beverages with their booty.


Even the glasses seem an authentic part of the costume.


“I spy with my little eye.”


Some buccaneers like the scary makeup.


“Arrrrrrhhhh you lookin’ at me?” – Photo: Chris Court


Every pirate needs his mobile barrel of grog.


The wenches are not afraid to be part of the battle.


A pirate and her parrot are the best of friends.


Would you mess with these marauders?


Our very own Captain Jack Sparrow.


Trust Jack Sparrow to get behind a woman when trouble’s brewing.


Seems that even the red coats had a Go Pro camera.


Will he sneeze or shoot?


A pirate queen makes her way down Harbour Drive.


Watch out for buccaneers after yer booty.


“I sense a change in the wind, says I.”