Residents are entertained year round with various events celebrating Caymanian heritage and customs. By participating in these fun and social events you are becoming a greater part of the local community. Numerous sporting events (walks, marathons, triathlons, etc.) and Culinary festivals (discussed under dining) are held throughout the year, which are generally fundraisers for local charities. Below are some additional events and festivals that are annual fixtures on the Cayman cultural calendar.

National Arts & Culture Awards An event to recognise those who attain a level of merit in their artistic discipline and contribute to the arts and heritage of the Cayman Islands.

Agricultural Show A traditional Cayman get-together, a fun family day out where you can meet Cayman farmers and their livestock, watch equestrian drills as well as enjoy live music and local and international fare.

Mardi Gras Kaibo comes alive on Ash Wednesday with thousands of people who drive or boat up for festivities that begin in the daytime and carry on well into the night.

Cayman Islands Orchid Show Held at the Botanic Park each year in early March. A fantastic display of orchids, with many up for sale.

Humane Society Annual Fur Ball Gala The Humane Societies’ biggest fundraising event complete with auctions and live music.

Cayfest This art and cultural festival showcases some of the best local talent in a variety of artistic displays: art and photography exhibitions and competitions, dance, music, poetry, plays and more. Celebrated at various locations and through different media, the festival includes open mic sessions, catboat regattas, play readings and fashion shows put on by local designers.

Cayman Carnival Batabano An explosion of Caribbean culture that brings the streets of George Town to life with steel pan bands, floats and parades with thousands of people dressed in flamboyant and colourful costumes.

Cayman Islands International Fishing Tournament Anglers compete in this much-anticipated annual event.

Rundown A night of entertainment and comedy which takes place all under a familiar Caymanian theme.

Flowers Sea Swim This annual popular event draws both Olympic-level and casual swimmers. Around 800 people take part in the one-mile swim that runs parallel to the Seven Mile Beach. Simply finishing the swim gives participants a one in five chance of winning some great prizes.

Jet Around Cayman Jet skiing is an extremely popular activity at any time of year in Cayman, but in June the real daredevils and thrill-seekers test their mettle in a round-the-island race.

Constitution Day Fireworks Celebrate the public holiday in Camana Bay and watch the fantastic fireworks display set the harbour aglow.

Culture Jam A “cultural happy hour” held every second and fourth Friday in June–August where people are welcome to come out and share their talents.

The Cayman Islands Breast Cancer Foundation Gala An annual fundraiser celebrating survivors and helping to raise funds for local non-profit organizations.

Legends Tennis Championships at The Ritz-Carlton A big event in the Cayman Islands that draws a number of impressive people. It is a star-studded event that is not to be missed!

The National Trust Gala Dinner An event in support of the National Trust that includes a dinner and live and silent auctions.

Pirates Week This national festival is celebrated on Grand Cayman then moves on to Cayman Brac and Little Cayman for a day each. During the festival Cayman’s heritage is celebrated with mock pirate invasions of the capital, float parades, music and dancing in the streets, fireworks and much more.

Annual Christmas Tree Lighting Festive family fun sets the spirit for the season. Watch as Camana Bay transforms into a sparkling wonderland with a giant Christmas tree, festive performances, caroling and a visit from Santa.

Cayman National Cultural Foundation Fundraising Folk Concert An event filled with traditional folk music.

Gimistory The Cayman Islands International Storytelling Festival, which brings people together from around the world. There is plenty of entertainment and admission is free.

Festival of Trees This week of festivities includes a display of stunningly decorated Christmas trees and wreaths and a special dinner auction in support of the Central Caribbean Marine Institute.

Parade of Lights A beautiful display of Christmas lights on the water as boats float along the harbour clad in colourful lights. Held in the harbour in either Camana Bay or George Town.

The National Trust Christmas Lights Tours Fundraiser Start your evening with a traditional meal followed by carols, all while taking in some of Cayman’s most beautiful light displays.


Cayman has an intriguing Caribbean heritage and culture that has derived from the island’s fascinating past. Cayman’s most famous heritage sites include Pedro Castle, St James and Fort George whilst The National Trust, The National Museum and The National Gallery all support Cayman with it's important slice of Caribbean history. Other important landmarks include Barkers National Park, The Botanic park and gardens and Hell with it’s limestone coral formations.