Pirates Week 2014 Flags be a-flyin’, maties!

It’s hard to believe that it’s already that time again, but the wind indeed be shiftin’, and on the horizon we see the skull and crossbones flappin’ in the salty air, indicating that ‘tis Pirates Week upon us. Wenches and buccaneers will be descending on the Cayman Islands for 10 days of grog, grub and lots of entertainment.

It all begins on Thursday, Nov. 6, going through to Sunday, Nov. 16, with so much merriment in-between, it’ll be hard for a pirate to keep up with it all. Luckily you can keep the full schedule close at hand, so you don’t miss a moment of the festivities.
Here are some of the highlighted events that are always top favorites with visitors and residents alike.  

Thursday, Nov. 6
CUC Pan In De City (Harbour Drive)
Pirates Week Kick-Off Party (The Wharf)

If you’re a fan of steel pan music, you won’t want to miss Pan In De City along Harbour Drive in George Town. There is nothing like a steel pan group to get you into the spirit of the Caribbean. Those unique sounds, mixing together to create beautiful music, are the perfect choice for a festival of this kind.
Come along, tap your toes, and join in the sights and notes of the islands.
You can then head to The Wharf, known for its annual Kick-Off Party, complete with live music, food and drinks on the waterfront. The Wharf is a legendary establishment, and a big enough venue to comfortably accommodate hundreds of revelers. It’s the only way to start off Pirates Week with a bang!


Friday, Nov. 7
Pirates Week 5K Run (Bayshore Mall)
Fireworks/Street Dance (Harbour Drive)

Healthy and sporty pirates and wenches will no doubt sign up for the annual Pirates Week 5K Run that starts at the Bayshore Mall in George Town. It’s a fun event, and is open to competitors of all abilities. Probably not a bad idea to start off the festival with a bit of exercise, considering the food and drink to come, but then there will lots of dancing to enjoy, so not a difficult way to burn calories.
Once runners have recovered from that bit of exertion, they can stick around for an absolutely spectacular fireworks display that lights up the night sky every year. The wonderful thing about fireworks of this size and glorious design is that no matter where you’re positioned downtown, or even along the coast, you’ll get to enjoy their color and majesty.
Stick around for the explosive performance of Kes the Band direct from Trinidad, live on stage. This amazing group will get the party going like you’ve never seen before!

Saturday, Nov. 8
Landing Pageant and Float Parade
(Hog Sty Bay)
Street Dance and Food Festival
(Harbour Drive/Shedden Road)

The landing pageant and float parade really need no introduction. They are the highlight of the festival, as ships and boats of all sizes and shapes, including the Jolly Roger, descend on the harbor, packed with buccaneers and marauders ready to do battle. As the scalawags “take” George Town, children and adults can enjoy the entertainment and pose with pirates for pictures.
Turns out that they’re not all bad in the end, and disputes are forgiven over a pint or three so the float parade can officially begin. Floats from different districts and groups, complete with music and costumes, make their way along the streets of the town at a slow pace, so everyone can see them in detail. It’s a terrific family event, so get a good spot along the route.
Once the sun goes down, it’s time for the street dance and food festival. This is arguably the biggest street dance of the 10 days, not to mention all the amazing local food you buy from lots of stalls. Bring your appetite – you’re gonna need it.

Sunday, Nov. 9
Children’s Fun Fair Day (Pedro Castle)
Underwater Treasure Hunt (Divetech)

Baby buccaneers and pirates-in-training can head to Pedro Castle for the Children’s Fun Fair Day, with lots of entertainment for the younger generation. Why should the adults have all the fun? Pedro Castle is a great backdrop for the day; the historic building and its surroundings really set the stage for a cultural celebration.
Scuba divers can head in the other direction to Divetech in West Bay, where “X” marks the spot for the Underwater Treasure Hunt. There are loads of valuable prizes to be won at this always-popular event, when divers scan the sea for clues to booty aplenty.
Sign up and with any luck you’ll be a winner!



Monday, Nov. 10 – Friday, Nov. 14
Heritage Days (East End, West Bay, North Side, Bodden Town, George Town)

Each district has its own unique flavor and vibe, and you can experience it all by visiting them through the week. Don’t miss out on the amazing food on offer! The local cuisine is one of the main draws for the district days. Yum!

Tuesday, Nov. 11 – Thursday, Nov. 13
Local Food and Crafts Market
(Cardinall Ave)

Tourists and residents will get a great chance to visit food stalls and shop for crafts in the convenient location of central George Town for three days in the middle of Pirates Week. Cardinall Avenue will be closed off to allow pedestrians to browse at their leisure.
Stop by for some lunch, or maybe even get some early Christmas shopping done. You’ll be amazed at the variety of lovely art and crafts you’ll find, and all made in the Cayman Islands.

Saturday, Nov. 15
Caybrew Cardboard Boat Race
(Hog Sty Bay)
Sentencing of the Pirates/Fireworks/Street Dance (Harbour Drive)

You haven’t seen hilarity ensue until you’ve witnessed the Cardboard Boat Race in Hog Sty Bay. Some dubiously seaworthy vessels take to the harbor to see if they can make the course without sinking.
There have been some pretty fantastical creations over the years, not to mention the costumes donned by the crew, but water is the great equalizer, and no matter how pretty your craft may be, whether she’ll be able to handle the relentless surge of the waves as you paddle furiously to the finish line is quite another story.
After the race you might as well stay in town for the always entertaining Sentencing of the Pirates, followed by a fireworks display, and the last street dance of Pirates Week. Go out in a blaze of glory!

Sunday, Nov. 16
Jerry Harper 10K Run (Seven Mile area)
Mickey Mouse Darts Tournament
(Mango Tree)

After all the drinking, eating and cavorting, maybe the best way to get back into a healthy lifestyle is to enter the brisk Jerry Harper 10K Run. Coach Harper is always happy to be in evidence, spurring runners on at that early hour of 7 a.m., as they take to their marked route.
You don’t have to be a sprinter to participate. Run, jog, walk…just come along and join in.
Then again, if you simply aren’t the kind of athlete to enter such a run, AND you enjoy your beauty sleep, the Mickey Mouse Darts Tournament might be more your speed at the Mango Tree. Bullseye!

Friday, Nov. 21 – Saturday, Nov. 22
Little Cayman Pirates Celebration

If you haven’t had your craving for all things buccaneering sated by the Grand Cayman Pirates Week, why not hop over to Little Cayman for a bit of a dance, float parade and costume competition? This sister island celebrates near the end of November, and if you haven’t been before, you’re missing out. Book a flight on Cayman Airways today, and see what all the fuss is about.