Top Cayman Islands Events and Festivals

The Cayman Islands is the rare Caribbean destination with two legitimate Carnival-like celebrations -- the traditional Batabano held in May and the anything-but-ordinary Pirate Week, which swaggers its way into Grand Cayman in November.

  • 01 of 07
    ••• A pirate ship launches a volley during the annual Cayman Pirate Week festival in the Cayman Islands. © Don McDougall

     One of our favorite Caribbean events begins each year with a invasion by sea as a pair of pirate ships sail into the George Town harbor to take the local governor captive. You'll be captivated by 10 days worth of swashbuckling fun including fireworks, concerts, road and swim races, the naming of a festival king and queen, parades, and even an ill-fated cardboard boat race.

  • 02 of 07

    Batabano Carnival

    ••• Batabano Carnival Parade in the Cayman Islands. © Cayman Islands Department of Tourism

     Batabano may be named after the sea turtles of the Cayman Islands, but there's no staying in your shell at this lively annual Carnival celebration celebrated everywhere in the Caymans but especially on Grand Cayman, which hosts the biggest jouvert celebration and masquerade parades. As in Trinidad -- home of the biggest Carnival of all -- visitors can take part in the parades (for a fee) and also join in the fun with pre- and post-Carnival parties, winding down on a beautiful local beach to sleep off all of the fun.

  • 03 of 07
    ••• © Horian Varlan via Flickr

     Storytellers from the Cayman Islands, the wider Caribbean, and around the world take part in this free annual cultural event, held in late November/early December as part of the islands' pre-Christmas tradition. The family friendly readings take part at local beaches, schools and community centers, and the events typically are accompanied by local food and drink.

  • 04 of 07
    ••• Chef Eric Ripert. via Facebook

     Celebrity chefs like Eric Ripert -- who helms the Blue restaurant at the Ritz-Carlton, Grand Cayman -- and Anthony Bourdain host this annual celebration of Caymanian and international food and wine at the Ritz-Carlton resort on Seven Mile Beach. The weekend-long even in January features cooking demonstrations, beach barbecues, a champagne brunch, dinner parties, and artisian marketplaces held at some of the islands' finest beaches and resorts.

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  • 05 of 07
    ••• © Cayman Islands Angling Club

     Anglers flock to the Caymans in late May and early June to compete in this annual tournament, held in the waters off Grand Cayman and Cayman Brac, with prizes for the top catches of marlin, tuna, and other game fish.

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    ••• © fiskfish via Flickr

     The name of this annual speedboat race is a little quaint -- rest assured, there's far more than $1 million worth of watercraft in the water when the flag gets raised for captains to start their engines off Grand Cayman's Seven Mile Beach each July. Races of both moderate- and high-performance boats are held, along with a jet-ski race, bracketed by several days of pre- and post-competition partying.

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     The Cayman Arts Festival is all about the classics, from orchestra to ballet to choir performances, each intermixed with educational programs designed to enhance the performing arts in the local community. Your tickets to the February shows include admission to some of the Cayman Islands' most important community gathering places, including the First Baptist Church, the Harquail Theater, and the historic Pedro St. James plantation.