Avast Ye Mateys! Why November is a Fun Time in the Cayman Islands

Cayman Islands Pirate Festival
Cayman Islands Dept. of Tourism

Whether you're a swashbuckler or a scallywag, consider charting a course in November for the Cayman Islands, which host 10 days of treasure-hunting and buccaneering during the annual Pirates Week National Festival.

The one-of-a-kind festival offers plenty of opportunity for families to engage in traditional Caymanian culture and speak, dress, eat and have fun like a pirate. The celebration kicks off with a steel pan party and ends with a “To Hell and Back” 10K Run and international swim meet. (The event references Hell, a bleak natural limestone formation with a small post office that lets you send home a postcard from Hell.) Best of all, every event during the festival is free for visitors.

In George Town, Grand Cayman’s capital, you can witness a just-for-fun pirate invasion, complete with two pirate ship vessels filled with “pirates” who invade the harbor and capture the island's governor. The week also includes heritage days with fireworks extravaganzas, costume contests, live music, street performances, games, food festivals, and a children's fun fair.

Highlights include a charity golf classic tournament, “Pirate Pooch Parade” for pirate dogs of all shapes and sizes, and an Illumination Night Parade featuring boats and yachts festooned in twinkling lights as they sail through the harbor.

Additional events will occur in Cayman Brac and Little Cayman before and after the official festival week. 

Note that the festival takes place at the tail end of hurricane season in the Caribbean, though the odds of a hurricane happening during your stay is statistically very small. Here are some tips on taking a vacation during hurricane season.