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 had 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.

For more information on Pirates Week, visit

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Grand Cayman

Nov. 10

Is it a pirate sword or a machete in disguise?

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 on

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 some of 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?

Nov. 11

The dragon leads the pack!

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.

Nov. 12

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.

Nov. 13

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 Street/Cardinall Avenue – 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.

Little Cayman

Nov. 17

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.

Nov. 18

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.

Nov. 19

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.

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