Cultural Celebrations

There’s a special time of year for everyone in Cayman, whether you’re looking for a party or a parade, an artsy fling or an athletic challenge. The beautiful beaches, natural adventures and exquisite accommodations of the Cayman Islands lure travellers year-round. The Cayman calendar has annual events that add even more fun and culture to the mix.


CAYFEST, or the Cayman Islands’ National Festival of the Arts, kicks things off in the last weekend of February each year. This celebration of all things creative covers just about every type and style of art: visual, music, theatre, film, fashion design and more. The festival focuses on local talent and on honoring Cayman’s diverse culture with events like the annual National Arts & Culture Awards, which recognizes artists, cultural animators and those preserving and promoting Cayman’s cultural heritage; the Cayman Islands Folk Singers in Concert, which highlights Caymanian and regional folk songs passed down from cultural icons such as ‘Aunt’ Julia Hydes; and the Red Sky at Night Festival, which features musicians, actors, dancers, and storytellers performing live for audiences, as well as regional films at George Town’s FJ Harquail Cultural Centre. The name Red Sky at Night comes from the old maritime rhyme “Red sky at night, sailors’ delight.”


Agriculture and farming is an often-overlooked yet integral part of the Caymanian way of life. The Cayman Islands Agricultural Society provides residents with information on anything from which vegetables to plant in a particular season to landscaping with tropical storms in mind. The 50th Annual Agricultural Show takes place at the Stacy Watler Pavilion on March 1, 2017. The Agricultural Society plans a wonderful show to highlight our early pioneers, pioneers and emerging pioneers in farming with several interactive displays, and much more. The Sister Islands also have their annual Agricultural Shows, held in March in Cayman Brac and Little Cayman, where the community comes together to show off produce, livestock, crafts and more. From food vendors to local artisans to fun attractions for kids, these events are truly an authentic local experience not to be missed.


Carnival celebrations are some of the Caribbean’s most colourful and exciting events, and Batabano in the Cayman Islands is no different. The main event, an adult street parade, features acrobats, stilt walkers and limbo dancers maneuvering amongst floats and throngs of revelers in fantastically flamboyant costumes. Visitors can watch from the sidelines, or take the leap and join the party people in the parade — all it takes is a little advance planning with one of the five “bands” who organize the festivities’ costumes, music and more. Many welcome visiting masqueraders with open arms. The adult parade is just that rowdy, perhaps a bit risqué and intended for adults. But that’s just one part of the Batabano fun. Annual festivities also include a children’s parade; a food festival; live concerts by soca stars; and Art In The Heart, an arts and crafts market. The event takes place on May 6, 2017.



October is Restaurant Month in the Cayman Islands. Restaurants all across Cayman create special menus that let foodies dig into some of the islands’ best meals, all for fixed prices during both lunch and dinner. Whether it’s a casual lunch break at Guy Harvey’s Restaurant & Bar, or an elegant three-course feast of short ribs and lionfish at Grand Old House, Restaurant Month in Cayman makes exploring the flavours of the islands easy and affordable.


Perhaps no other Caribbean nation celebrates its pirate legends and cultural heritage quite like the Cayman Islands, which erupts into a festival of spectacle and pageantry during its annual Pirates Week in November. The events include mock “invasions” of pirates, along with Heritage Days in each district, a series of parades, parties, costume contests, happy hours and more, stretching across all three islands. The festivities that take place in Grand Cayman this year will include a landing pageant, two parades, food festival, street dance, a cardboard boat race, a children’s fair, an underwater treasure hunt and more. But it all comes to an end a week later, when the locals reclaim the islands and the marauding pirates are “sentenced” during a pageant that is followed by fireworks, a night parade and a street celebration of food and dance. Whether you are visiting Little Cayman, Cayman Brac or Grand Cayman for their individual Pirates Week celebrations, you are sure to have fun.


Years ago, before text messaging and Tumblr and Twitter, people expressed themselves the old-fashioned way: by telling stories to each other, face to face. And in the Cayman Islands, storytelling soon became elevated to an art form. On front porches or by the beach, in churches and in schools and just about everywhere else, storytellers were the people who brought the community together. Today, in an annual celebration at the end of each year, the Cayman Islands International Storytelling Festival, better known as GIMISTORY, honors and continues that tradition. Recognized as one of the world’s top storytelling festivals, the event gathers storytellers from Cayman, the Caribbean and beyond. These talented performers captivate audiences across the three islands, with events under the stars in parks, on beaches and even invading private gardens. It’s a throwback to a time when Caymanians had to make their own entertainment, perfectly complementing Cayman’s historical attractions. But it’s also a way for adults and children alike to fire up their own imaginations in ways they likely haven’t done since they laid hands on their first iPhone. What better way for locals to revisit the cultural happenings of the previous year — and what better way for visitors to engage and experience the culture of Cayman? Delicious local food, such as fish and frittas and swanky, is also served up at each venue.


No, the pilgrims didn’t famously break bread with native people here in the Cayman Islands, but that doesn’t mean locals don’t have plenty to be thankful for as they get together with family and friends to count their blessings. The Cayman Islands’ version of Thanksgiving, which takes place during the weekend of the first Sunday in December, celebrates the unique culture and heritage of these islands. Local markets sell homegrown produce; musicians fill the air with traditional Caymanian rhythms; storytellers enthrall listeners with classic Cayman tales. And it all culminates in a massive dinner of traditional Caymanian delights, with participating restaurants serving special menus on that Sunday.