The return of Pirates Fest (formerly known as Pirate’s Week) has been updated for residents and tourists, with the events being spread over a few months. Leading up to the long weekend of the 11-14th November, there have already been celebrations that have taken place, including Grand Cayman’s District Days and the Little Cayman Pirates Fest. This weekend is the main event so you need to start planning ahead!

Thursday 10th November

The Pirates Fest Happy Hour & Kick-off Party will mark the beginning of this weekend. Note that admission is free to enter the Royal Watler Terminal with the event taking place at Snappers Bar & Grill. They’ll be selling food and drinks for guests and this is a chance to mingle with local and international pirates from 6-11pm.

Friday 11th November

From 6pm onwards you can stop by Cayman Cabana for their Wenches Party. This the perfect spot for a party as they have a massive bar and deck area for people to enjoy live music, DJs and hang out with other pirates. Get in the mood and wear your best costume because they will be doing a pirates & wenches costume competition on the night.

Saturday 12th November

Prepare for an all day affair spent in the centre of George Town. First up is the Cardboard Boat Regatta in Hog Sty Bay from 1-2:30pm. If you’ve never witnessed this you should because it is hilarious to watch. Participants have been working hard for days /weeks in an attempt to make a functionable boat out of cardboard and tape. They are expected to paddle around a course in the Bay, but as you can imagine many of these will not make it. Half will disintegrate within minutes of being in the water, whilst others surprisingly pull off the task and make it to the end.

You may as well stay where you are, because shortly after this (3pm) is when the Pirate’s Landing starts. You’ll watch the pirate ship make its way into the Bay, and as the pirates unload they fight through the red coats to try and capture the governor. Once this task has been completed they lead the way down the streets and behind them will follow our annual float parade and music.

Feeling hungry? From 2pm you can visit the RBC & Kir Freeport parking lots to try some authentic Caymanian cuisine. You can’t miss the variety of vendors who are covered with tents. This is the best time to try Cayman Style Beef, Conch Stew, Turtle Stew, Jerk Chicken, Cassava Cake and more. I tend to visit the stalls hailing from East End in particular, but when in doubt just know that a long line means that good food is sure to follow!

If you’re still around then watch the firework show from 9pm in the Bay. People tend to linger around town from afternoon into evening as they will drink, eat & socialise preferably while wearing pirate garb.

This weekend may be the most familiar and jam-packed for Pirates Fest, but there are still a few events coming up next week such as the Cassava Cake Competition, Conch Fritter Competition, Pan In De City (the steel pan competition), the Finale Fireworks show and even a beach clean-up by Plastic Free Cayman. Visit to learn more!