A Guide to Pirates Week

Pirates Week is a personal favourite for many of the locals in Cayman. It’s become a lovely tradition for families, teenagers and adults alike. It’s been going on for over 40 years and is still wildly popular. 

The traditional activities begin with the ‘invasion’ of the pirates, capturing the Governor and taking him/her on-board their pirates ship. Everyone lines the streets in town to watch this light-hearted, pirate-filled showcase. Following this, the festivities are kicked off with a bang! Quite literally, as wonderful fireworks light up the night.


Another tradition that’s a Pirates week crowd-pleaser is the costume competition and parade. Thousands of people stretch from the town centre down Seven Mile Beach to watch this spectacle take place. All floats, created and inspired by local people and businesses, display pirate or sea-related costumes, which is absolutely mesmerizing for the crowd. The costume competition of some of the most realistic-looking pirates flows through amongst the floats, engaging with the crowd. If you want to survive the parade, whether you’re in the crowd or on a float, make sure to drink bottles (and bottles) of water! Even though it’s November, the heat takes no prisoners. It’s not only about surviving the parade; it’s about making it to the evening street dance, which often includes enthusiastic steel pan players, festival flare and a lively Caribbean atmosphere. 

Pro tip: don’t try to drive into town; you’ll waste your time circling in figure 8’s. If you’re coming to the Island specifically for Pirates Week and looking for somewhere to stay you should consider Margaritaville for the central location, ie. you can get to the essential places such as town centre, Hurley’s supermarket, the beach and various restaurants by foot. There are also a variety of great hotels on Seven Mile Beach as well as apartment rentals that could be the perfect location for you depending on your individual needs – but get on it fast as accommodations book up quickly around this time. 


There’s a great cultural aspect to Pirates Week, which often revolves around the great local cuisine. This is often made by chefs, and even families with a passion for creating traditional dishes, at the Food Festival on the waterfront. A visit to the Food Festival is a must, as there are tones of tasty Caymanian dishes to choose from, all for around $10-15. 

If you’re looking to do Pirates Week from start to finish and would also like to see our sister Islands, you’re in luck. A nice way to tie it all together is to go to Cayman Brac for the first week - partake in all of their festivities, then head to Grand Cayman for the second week, finishing off in Little Cayman for the third weekend. What could be better?