It’s hard to believe that Pirates Week is turning 40 this year. When you look back at the media archives from the early days, you see the beginnings of what would become one of the Cayman Islands’ premier annual festivals, bringing wannabe swashbucklers from far and wide to these shores.
Up through 2016, the Grand Cayman celebrations were running over 10 days, starting on a Thursday and finishing two weekends later. However, this year there is a change. The organizers have decided to tighten the schedule and hold many events over one long weekend. Should be a pretty awesome time!
As ever, Cayman Brac has its festival first (Nov. 3-5) followed by Grand Cayman (Nov. 9-13), and then finally Little Cayman has its say (Nov. 17-19).
Now, more than ever, it’s important to know what’s going on when, as the schedules have changed from previous years. Here are some of the highlights you won’t want to miss.
3:30 p.m. – midnight ∙ Watering Place
Pirates and wenches gather for possibly the longest happy hour in history. The event leads into the Pirates Party Kick-Off Dance, going into the wee hours, and christening the official start of Cayman Brac’s celebration.
8 a.m. – 11:45 p.m. ∙ Heritage House
The day begins with Heritage Day events, including demos, craft stalls, live music and a traditional tea party. The much anticipated Float Parade takes to the streets at 3:30 p.m., followed by the Happy Hour and Finale Party from 6-11:45 p.m.
11 a.m. – 2 p.m. ∙ La Esperanza
The Pirates Farewell Lunch is a Cayman Brac tradition. No matter what marauding has gone before, parlay is reached between the pirates and the islanders and all fights are forgotten over some good food and grog.
7 p.m. ∙ Harbour Drive
George Town comes to life with the CUC Pan In De City steel pan competition. Junior and senior steel pan bands showcase their talent in glorious harmony at this huge gathering of musicians.
9 p.m. – 2 a.m. ∙ Royal Palms
The party crowd makes its way up to the Seven Mile Strip and Royal Palms for the Pirates Week Kick-Off Party. Listen to the sounds of the best local rhythms as you dance the night away alongside local and visiting Pirates.
3:30 – 6:30 p.m. ∙ Harbour Drive
Savvy scalawags know that a bit o’ exercise before the big night is a good idea, and what better way to get the muscles moving than by signing up for the Pirates Week 5K Run? Just a quick nip around the George Town area, starting and ending on Harbour Drive, and you’ll be ready for the festivities later on. Register at www.caymanactive.com.
6 p.m. – 2 a.m. ∙ Shedden Road
You can’t have Pirates Week without delicious, homemade dishes to “nyam” upon. The Food Festival is set up in the parking lots of Royal Bank of Canada and Kirk Freeport along Shedden Road for ease of access off Harbour Drive. From traditional turtle and conch stews and other Caribbean favorites to international Asian and Hispanic fare, there is plenty to suit all palates. Grab yourself some platefuls to absorb the beverages from the bar.
7:15 – 8:45 p.m. ∙ Harbour Drive
Who will be crowned Miss Festival Queen? Find out when a bevy of beauties compete for the ultimate prize. The pageant starts at 7:15 p.m., followed by an incredible firework display at 8:30 p.m. Get the whole family together for a good view of the harbor and watch the lights reflect off the water.
10:30 p.m. – 2 a.m. ∙ Harbour Drive
Dance the night away to live music under the stars. What else needs to be said?
11 a.m. – 2 p.m. ∙ Hog Sty Bay
One of the real highlights of Pirates Week is the Caybrew Cardboard Boat Race. This hilarious competition pits teams of rowers against each other in crafts created solely from cardboard and a few other allowed materials (duct tape and glue). It is a riotous event and always draws a huge crowd.
2 – 6 p.m. ∙ Harbour Drive
The pre-landing entertainment begins at 2 p.m. with acrobats, waterfront stunts and dance performances, all followed by the Pirates Invasion where pirates and wenches “take” the islands’ capital with swordfighting and much “arrrrr”-ing. Then comes the float parade – great viewing for all ages.
9 p.m. – midnight ∙ Harbour Drive
It’s dancing time, with the second street dance in a row! Food will be on sale all night, along with bars serving up drinks and live bands and DJs providing the music.
Noon – 4 p.m. ∙ Pedro St James
The Children’s Fun Day will be held, as usual, at Pedro St James in Savannah. This is a terrific day out for the kids and parents. Lots of activities and entertainment to keep young scalawags happy.
Midnight – 4 a.m. ∙ Harbour Drive
Night owls can get ready for Soaked, the wet fete that starts at midnight and continues until the sun nearly rises. Don’t wear clothes you care about – they’ll be getting more than moist.
8 a.m. – 6 p.m. ∙ Albert Panton St/Cardinall Ave
Instead of visiting individual district days, members of the public can visit all of them – east to west – in one spot.
7 p.m. – midnight ∙ Harbour Drive
The Sentencing of the Pirates starts the evening off, followed by the Illumination Night Parade where thousands of colorful lights adorn floats and bands – it’s a bright and vibrant spectacle for all ages.
At 8:15 p.m. the night sky lights up with a grand finale firework display, which leads into the street dance and food festival running until midnight. The perfect end to another fantastic Pirates Week in Grand Cayman.
8 p.m. – 2 a.m. ∙ McCoy’s Lodge
The Kick-Off Dance is a great excuse for a party, starting off the Little Cayman celebrations in fine form.
3 – 5:30 p.m. ∙ Head O’ Bay
It’s smaller than the float parade on Grand Cayman, but no less fierce. Islanders and visitors gather to see what creative floats have been devised by Little Cayman’s buccaneers.
5 p.m. – midnight ∙ Hungry Iguana
The costume competition is one of the favorite events here, as is the Pirate’s Dance which follows immediately afterwards. Wear comfortable boots ‘cos you’ll be bopping ‘til midnight.
11 a.m. – 4 p.m. ∙ McCoy’s Lodge
It’s the last farewell lunch for the Pirates, as Nov. 19 marks the official end of all the celebrations of the three islands for 2017. It should be a doozy!
For more information on Pirates Week, visit www.piratesweekfestival.com.