The annual Pirates Week festival, held in Cayman since 1977, is getting a face-lift as it marks its 40th iteration this year.

Major changes were announced to the schedule Tuesday, which will condense the festival, formerly spanning two weekends, into five days.

According to a tentative schedule released by the Pirates Week Festival, the entire event will take place on Grand Cayman between Thursday, Nov. 9, and Monday, Nov. 13, this year. Pirates Week festivities will be held in Cayman Brac between Nov. 3 and 5 and in Little Cayman between Nov. 17 and 19.

The Heritage Day events, which had been held in each of Grand Cayman’s five districts, will be winnowed down into one all-day event in George Town on Nov. 13, the last day of the festival.

“Spectators will have the opportunity to wander from West Bay to East End in just a few steps, while stopping off in George Town, Bodden Town and North Side along the way,” according to a statement from Pirates Week Executive Director Melanie McField.

- Advertisement -

Meanwhile, all of the major Pirates Week events will be held during one long weekend, with Nov. 13 being a holiday Monday. For instance, the popular cardboard boat races are set to be held starting at 11 a.m. in Hog Sty Bay. They will end around 2 p.m., about an hour before the pirates landing and float parade at 3 p.m.

The “Trial of the Pirates” – the traditional end of the festival – will take place around 7 p.m. Monday, following the end of the George Town Heritage Day event.

Events on Friday, Saturday and Monday nights feature various street dances.

A number of other events, including a swim meet, a 5K sea swim, the Pirate Pooch Parade, two Harbour Drive fireworks displays and the children’s fun day on Sunday, will be packed into a tight Friday-Monday schedule.

The start of the festival on Thursday, Nov. 9, will feature a Pirates Week happy hour, the steel pan competition and a kick-off party downtown from 9 p.m. that night until 2 a.m. Friday.

Festival organizers this week said they were not content to “stand still and regurgitate the same winning formula” from previous years.

One issue in past years was that the previous 10-day festival, which started on one weekend in October or November and ended during the next, made it difficult for tourists from overseas to attend both weekends.

Also, some of the daily district day/heritage day events were poorly attended and were not known to visitors to the islands.

Festival organizers are banking on support from the local community, asking at least 40 individuals and private sector businesses to contribute at least $1,000 sponsorship each to finance the event.

- Advertisement -

Support local journalism. Subscribe to the all-access pass for the Cayman Compass.

Subscribe now


  1. I think the comment about the length of the ‘festival’ sums the problem up nicely. In 2015 hotels and booking sites were still offering room rate specials a few days before Pirates Week kicked off. That rather gives the impression that it’s not exactly pulling the tourists in any more. In fact it might well be that the disruption caused by Pirates Week is becoming counter-productive.

    I’m not even sure that cutting it down to five days is enough. You could easily cover the main events over a long weekend and that in turn would fit in perfectly with the kind of short breaks the majority of tourists seem to favour at that time of year. This might actually be case where less really could mean more.

  2. My memories of the Pirates Invasion include deafening explosives thrown into the harbor water as the ship arrives.

    I have to wonder what effect the shock waves and pollution have on the fish. Can’t do them any good. Not to mention the ears of the crowds gathered.