Cayman Islands Pirates Week Festival 2019

Travel Tips |

Buccaneering legends will come to life this November for the Cayman Islands Pirates Week Festival. Across 11 action-packed days, this one-of-a-kind annual event celebrates our maritime heritage and the indelible era of swashbucklers, bringing locals and visitors together in true Cayman fashion.

Cayman Pirates Week 2019 will feature an electrifying program of family-friendly events. Spectators of all ages can enjoy street dances, fireworks displays, a treasure hunt, a mock pirate invasion, parades and Heritage Days, all enhanced by colorful costumes, infectious music and delicious traditional cuisine. This November, there’s no better place to be in the Caribbean!

What to expect during Pirates Week in the Cayman Islands

The Cayman Islands’ National Festival takes place across all three islands, each hosting a lineup of activities, food fairs and entertainment. The celebrations begin on Cayman Brac (November 1-3), move to Grand Cayman (November 7-11) and wrap up on Little Cayman (November 15-17).

Pirates Week on Grand Cayman: November 7-11⁠

Grand Cayman kicks off five days of buccaneer-themed fun on Thursday, November 7, with a party at Royal Palms Beach Club. The merriment continues on Friday with the crowning of the Festival Queen, a kid-friendly street dance, dazzling fireworks along Harbour Drive and the much-anticipated food festival, which showcases some of Cayman’s tastiest dishes.

On Saturday afternoon, join fellow revelers to witness a four-decade-old tradition as George Town Harbour sets the scene for a mock pirate invasion. Two old-time ships sail into the capital city, drop anchor and attempt to capture the governor in a rousing reenactment of mayhem and mischief. After the good-natured raid, spectators line the streets for a grand float parade.

Throughout Grand Cayman’s five-day festival, enjoy sports competitions, a Children’s Fun Day, a pet parade, teen dances, spirited parades and the not-to-be-missed “Sentencing of the Pirates.” Plus, participants can test their pirate know-how during the cardboard regatta and underwater treasure hunt! 

The festivities then move into a celebration of Cayman’s Heritage Days (November 12-16). Each of Grand Cayman’s five districts showcases its unique culture through demonstrations, crafts, music and, of course, plenty of local food vendors.

Kid-friendly Pirates Week events

Pirates Week offers family-focused events that are suitable for all ages. Little ones will love watching fireworks burst above the bay, and the good-natured pirate invasion, lively street dance and animated parades will thrill the whole family. Youth can enter the cardboard regatta in their age division, and our annual Children’s Fun Day features a bouncy castle, waterslide, games, face painting and plenty of pirate-themed activities.

Pirates Week tips

  • For top-notch fireworks viewing, reserve a table at a restaurant by the bay. Lobster Pot, Guy Harvey’s, Casanova and other waterside venues offer prime seating with unimpeded views.
  • Carry plenty of water and sunscreen, and take time to rest and rehydrate in the shade.
  • We encourage costumes! In lieu of bringing your eyepatch, tri-corner hat and ruffled shirt from home, the Pirates Week store in George Town offers a wide selection of attire for all ages.

For the full event schedule, visit

Stay with Luxury Cayman Villas during Pirates Week

Elevate your Pirates Week experience with a stay at one of Luxury Cayman Villas’ beachfront retreats. Enjoy the spectrum of festive events, knowing you have a place of comfort and calm to return to at the end of the day. We hope you join us this November to follow in the footsteps of piratical legends and lore!