Cayman is fortunate to have lots of events throughout the year, but they depend on local support to survive and thrive.
Events take a huge amount of planning, investment and manpower to stage, with many people giving countless hours and weeks of their time to ensure they succeed.
So, get behind these wide-ranging festivals, gigs and cultural showstoppers to make them a success and safeguard the enjoyment and entertainment for years to come.
Here is a line-up of the larger events to support in the year ahead:
CAYMAN RESTAURANT MONTH
October celebrates Cayman’s local dining scene, with the month-long event featuring a diverse array of culinary offerings. Organised by the Cayman Islands Tourism Association, participating restaurants feature fixed price lunch and dinner menus.
CAYMAN COCKTAIL WEEK
The last seven days of Cayman Restaurant Month incorporate Cocktail Week. The event celebrates Cayman’s cocktail culture with an array of cocktail parties, tastings, demonstrations and culinary events.
PIRATES WEEK
Held in November, this national festival takes over the whole of Grand Cayman with a parade, heritage days, music, street dances, local food, fireworks and other swashbuckling fun. Popular events include a mock pirate invasion, cardboard boat regatta and float parade. The Sister Islands also host events.
CAYMAN ISLANDS TRIATHLON
Athletes can choose from a sprint triathlon, or Olympic distance triathlon which has individual, two- or three-person relay options. Organised by the Cayman Islands Triathlon Association, and taking place on beautiful Seven Mile Beach, this event attracts a strong field of local and overseas participants. Held annually in November.
CAYMAN ISLANDS MARATHON
The Walkers Cayman Islands Marathon takes place on the first Sunday in December every year. One of the biggest sporting events on-island, it features a full marathon, half marathon, four-person relay and a kids fun run. The event is popular with both local and visiting runners, alike.
CAYMAN COOKOUT
Eric Ripert and an impressive roster of some of the world’s most renowned chefs attract the crowds to Cayman Cookout, annually, in January. The weekend at The Ritz-Carlton, Grand Cayman, is filled with tastings, demonstrations, tours and dinners, featuring chefs, wine and spirits experts. Well-known names include Andrew Zimmern, Kwame Onwuachi, Angie Mar, José Andrés and Emeril Lagasse.
CAYMAN ARTS FESTIVAL
Cayman’s largest performing arts festival attracts world-class artists for a week of stellar performances including jazz, classical and chamber music, as well as dance and visual arts events. Held annually in February.
COCO FEST
Coco Fest celebrates the Cayman coconut, preserving its ties to the islands’ culture and heritage. Held in February at Pedro St. James, the festival features food, products, demonstrations, and crafts made from the coconut. Presented by the Cayman Islands National Attractions Authority.
AGRICULTURE SHOW
Held annually on Ash Wednesday, the Agriculture Show on Grand Cayman is a favourite family event, where farmers showcase livestock and sell produce. Enjoy music and entertainment, food booths, horse riding and a petting zoo, as well as arts and crafts stalls. The agriculture shows on Cayman Brac and Little Cayman usually take place in the weeks following Grand Cayman’s event.
CAYFEST
The Cayman Islands National Festival of Arts, Cayfest, is an annual celebration hosted in March by Cayman National Cultural Foundation. It showcases the islands’ cultural diversity and artistic talent. Red Sky at Night has been Cayfest’s anchor event, featuring music, dance and storytelling, as well as a market showcasing works by local artists.
LIVE SEAFOOD FESTIVAL
Held in the third week of March, this event showcases a variety of ocean-inspired flavours, with a focus on sustainability. Some of Cayman’s best chefs cook up a storm on Seven Mile Beach, with the vibes ramped up by live music.
CAPELLA
This one-day music festival features well-known international artists alongside talented local performers. In 2025, headline acts featured the likes Ashanti, Clean Bandit, Gramps Morgan, Ky-Mani Marley, Alaine, Naliah Blackman, and DJ Puffy. The event takes place in March at Festival Green, Camana Bay, with the 2026 edition expected to be just as thrilling as previous years.
TASTE OF CAYMAN FOOD & DRINK FESTIVAL
The one-day event, usually held in April, features live cooking demonstrations, food and wine-tasting booths, local entertainment and family activities. It takes place on The Green at Camana Bay.
CAYMAN ART WEEK
A week-long curated programme of art gallery events, Cayman Art Week is held in May and is highly anticipated each year. Look forward to gallery and studio visits, pop-up exhibitions and more, all accessible by free Cayman Art Week bus tours.
CAYMAN CARNIVAL BATABANO
Cayman’s national carnival features music, dance and colourful costumes in true Caribbean fashion. Thousands of spectators line the streets to watch the parade, where participants showcase creative costumes, choreography and floats. Held annually in May, the name Batabano is a nod to Cayman’s turtling heritage as the word refers to the tracks left in the sand by sea turtles.
CAYMAS CARNIVAL
Revellers take to the streets to showcase spectacular costumes, music and dance, embracing island culture and heritage. The street parade is a carnival of mas (short for masquerade) bands, each with its own colours and theme. Held in July, CayMAS includes soca and steel pan competitions, parties and fetes.
OUT OF THIS WORLD MUSIC FEST
Since launching in 2023, the huge success of this music event has secured its spot as a highly anticipated annual occurrence in May. Along with an impressive roster of local talent, past international guest artists have included Ludacris, Sean Paul, Busta Rhymes and Elephant Man.
FLOWERS SEA SWIM
Attracting both novices and Olympians from Cayman and around the world, the Flowers Sea Swim is one of Grand Cayman’s flagship sporting and charity events. It is hailed as one of the world’s richest open water swimming events due to its vast array of prizes. The charity swim takes place in June, with all registration proceeds going to Cayman’s Swim Free programme to teach children how to swim.
*Visit the event websites for dates and event information.
This article originally appeared in the 2025 Love Local newspaper supplement.
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