Caymen Pirate Festival 1Does your Captain Kid have a passion for pirates?  Aye Matey, it’s  a disorder many lads and lasses suffer from.  Imagine being a real life pirate of the Caribbean on your next family vacation! You can do just that, every November at the annual Cayman Pirates Week Festival.

Although it’s called Pirates Week, it’s actually 10 days filled with parades, fireworks, even a storming of the former city hall, now a museum, by costumed pirates. Two historic tall ships then sail into the harbor and “capture” the Governor, as bystanders cheer.

cayman1Welcome Aboard the Jolly Roger

We weren’t able to visit the Cayman Islands in November, but we still got to enjoy the pirate’s life aboard the Jolly Roger, a two-thirds replica of Christopher Columbus’ ship, the Nina. This is one of the most popular family tourist attractions on the island of Grand Cayman, allowing young and old to live out their pirate fantasies.


Our two hour sail was filled with high seas hijinks and tons of fun for the kids.  Costumed pirates made kids swab the deck, then put one of the dads on mock trial and made him walk the plank.  You can imagine the screams of delight as dad was found guilty of limiting sweets and screen time!  Soon after, we all walked the plank, jumping into the ocean to take a refreshing swim in the most beautiful blue water you can imagine.

cayman2If you’re looking for a grand adventure, grab your eye patch and drop anchor in Grand Cayman. Your family’s likely to find a treasure trove of fun!   This year’s Pirate Festival runs from November 10- 20.

Disclosure:  We were guests aboard the Jolly Roger and the Cayman Islands Department of Tourism sponsored parts of our trip, but as always, the opinions expressed here are my own.