In 1977, after a very long absence, pirates once again landed on the shores of Grand Cayman, zealously disembarking their ships and trawling the streets of George Town, swords raised.

Far removed from an actual invasion, the landing was all part of a carefully planned national festival, aimed at attracting visitors to Cayman during the slower tourist season.

While Cayman’s real history with pirates may be vague and probably minimal, that does not stop us adopting the intrigue and allure of pirate legends that is enjoyed by our wider region. As such, the popularity of the Pirates Week festival has kept it going for 41 years to date.

2018 festivities

This year’s festival will follow a similar schedule to previous ones, with it all starting in Cayman Brac for three days of events, including a bonfire and Kick-Off Party, heritage displays, a parade and fireworks, from Nov. 2-4.

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Cayman Brac

Even if you are flying over from Grand Cayman and cannot manage to get to Cayman Brac before Saturday, do not worry – there will still be plenty of festivities for you to enjoy.

It’s all happening at Watering Place this Friday night, with Happy Hour and the Kick-Off Dance. The latter is scheduled to run from 5:30 p.m. to 2 a.m. so pace yourself, buccaneers.

Assuming you do not feel like cannons are exploding in your head the next day, you can attend the Heritage Day events, which features craft stalls and live music, followed by the Float Parade starting at 5 p.m.

Look to the skies around 8 p.m. Saturday for the impressive fireworks display as part of the bonfire night. Next day, you can head to the Pirates Farewell Lunch, from noon to 3p p.m., before driving (or flying) home.

Grand Cayman

It’s Grand Cayman’s turn next, with a jam-packed schedule from Nov. 8-12. The Pirates Week Kick-Off Party starts proceedings on Thursday at Royal Palms until 2 a.m., Then, walkers and runners hit the streets of George Town the next day for a 5K run/walk along Harbour Drive. Probably a very good way to wipe away the grog cobwebs from the night before.

If you are hankering for a good meal after all that activity, Shedden Road in the heart of George Town plays host to the Food Festival on Nov. 9, which showcases local and international dishes. Feast upon traditional turtle and conch stew and a variety of Asian and Hispanic fare from 6 p.m. to 2 a.m.

The Festival Queen Contest, a fantastic firework display on the harborfront, and the Pirate Star singing competition round off the day’s events, all topped off with the popular street dance which sees the capital’s roads flooded with revelers around the main stage.

Jump aboard the Big Island Schooner and watch the fireworks from the sea! A free welcome drink will be provided and booze coolers are also welcome on board. Departure will be from the South Terminal in George Town at 7 p.m. (meet at 6:45 p.m.). Fireworks go off at 8 p.m. Adults are $40 and children aged 3-12 years old are $20. Email [email protected] or call 949-5078 to sign up.

Tickets for the Waterfront Sound Invasion, starring Beenie Man and Bunji Garlin, as well as local DJs and bands, start at $30 and can be bought at The concert begins at 7 p.m. and ends at 3 a.m.

The swashbuckling fun continues on Nov. 10 as early birds hit the water for the 5K Sea Swim at 7 a.m., and four-legged friends strut their stuff in the Pirate Pooch Parade on Harbour Drive at 9 a.m.

The popular Cardboard Regatta at noon sees impressively homemade cardboard boats attempt to parade the waters in George Town harbor to win cash prizes. If you have never seen this race before, you do not know what you are missing. It is a hilarious event with many crafts not making it to the finish line before they disappear in cloud of waterlogged cardboard.

You will then want to secure your vantage point in anticipation of the pinnacle event of the day – the Pirates Landing at 3 p.m. This spectacle sees Cayman invaded by boat loads of pirates who capture the “governor” and begin their weekend takeover. Of course, all become friends in the end, just in time for the Float Parade along Harbour Drive.

The National Song Competition and round two of the street dance finish off the day.

If you still have energy left, Nov. 11 sees more events take place islandwide. A 10K run – ‘To Hell and Back’ – takes place in West Bay; the Children’s Fun Day entertains youngsters at Pedro St. James from noon to 4 p.m.; and an underwater treasure hunt could score one or two scuba pirates some serious booty. Entrance fee is only $25 for the treasure hunt at Sunset House and includes tanks, weights and snorkel gear. The hunt begins at noon.

Nov. 12 is a public holiday, so no need for weary marauders to head into the office. Good news for night owls, as the Soaked Pirates Week Wet Fete is happening on Harbour Drive from midnight to 4 a.m.

The Culture Shop and Food Festival will be on Cardinall Avenue from 9 a.m. to noon, followed by the Culture Jam Contest showing the best of Cayman’s talent on stage.

You can relax in town or head home for a nap, but whatever you do, do not miss the Sentencing of the Pirates at 6:30 p.m. when the dastardly pirates are finally called to answer for their crimes. This court case is naturally followed by the Illumination Night Parade on Harbour Drive, starting at 7:15 p.m., and then more fireworks before the final street dance of Grand Cayman’s celebrations.

Little Cayman

Little Cayman gets its piece of the pirate pie once Grand Cayman’s festivities are over. From Nov. 16-18, the smaller Sister Island comes alive with entertainment.

On Nov. 16, there is the Kick-Off Dance and Fireworks.

Next, on Nov. 17, is the Float Parade. Always a lot of fun, it’s great to see what the islanders and visitors come up with.

From 5:30 p.m., there is the Costume Competition and Pirates Dance at the Hungry Iguana bar and restaurant. The party goes until midnight.

Finally, tuck in to the Pirates Farewell Lunch at McCoy’s Lodge. The poolside barbecue is the perfect way to end Pirates Week 2018.

For a full schedule of events and links to tickets for the Waterfront Sound Invasion Street Dance in Grand Cayman, visit

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  1. 11 November is Remembrance Sunday and 12 November is Remembrance Day (Observed). This is the centenary of the Armistice, a sombre occasion to pause and remember those who died to protect our freedoms. Remembrance Sunday and Remembrance Day deserve to stand on their own merits and used as a backdrop for the end of “Pirates” Week. Every Remembrance Sunday wreaths are laid at our cenotaph “lest we forget”. It is an important part of the Cayman Islands’ history and culture, a real and tangible part unlike the made up myth of “Pirates” Week. Nothing could be more antithetical to the centenary of the Armistice than glorifying violence, terror and misogyny. It is a shame that the organizers chose not to remember that.