Food & Drink

Live (and Drink) Like a Pirate During the Cayman Islands’ Pirates Week

If a pirate’s life really is for you, then get yourself down to the Cayman Islands ASAP. Pirates Week (which is actually more of a Pirates Month) is already underway, and the swashbuckling waits for no one.  

The festival, which is celebrating its 40th anniversary this year, island hops every November from Cayman Brac to Grand Cayman and finishes up in Little Cayman. There’s a fake pirate invasion (during which the pirates capture the governor), parades filled with pirate ship floats, fireworks, costume contests, cardboard boat races and, of course, lots of rum—essentially all the fun parts about piracy without any of that nasty violence.

This celebration isn’t just tapping into Pirates of the Caribbean fandom, it’s based in some serious history. During the mid-1600s through the early 1700s, the islands acted as a home base for some of the world’s most notorious pirates, including Edward Teach (better known as Blackbeard) and Henry Morgan (you’ll recognize him from the label on your favorite spiced rum). Pirates Week recognizes and commemorates that important (if bloody) era of peg legs and treasure maps with parties, dancing and lighthearted faux pillaging.  

Costumes are encouraged, and you’ll see folks wearing everything from their finest, most historically accurate tri-corner hats, to those doing their best Johnny Depp impression, to others who are satisfied to slap on an eyepatch and call it a day. And then there’s the booze. Bars across each island host happy hours and feature drink specials, and there are even bar crawls for the truly dedicated. It’s legal to drink on the beaches in the Cayman Islands, so you can really live that pirate life with your bottle of rum. Yo ho ho.