At Red Sail Sports, we know Grand Cayman as a paradise for adventures at sea. But throughout the year, the island is bursting with cultural festivities, community spirit, and delicious flavors. With this lively calendar, you can celebrate everything from food and culture to history and art.
We’ve created this guide to festivals and events in Cayman, from Batabano to Cayman Cookout, allowing you to discover the island beyond the beach. Of course, in between each event, our Grand Cayman Boat Tours are always available. If you have any questions about our activities, don’t hesitate to contact us. For now, let’s unpack the Cayman events calendar!
Cayman Cookout: Mid-January
For epicureans, nothing beats the Cayman Cookout. Hosted at The Ritz Carlton on Seven Mile Beach each January, this world-renowned culinary festival attracts some of the biggest names in food and wine. Guests can experience intimate cooking demonstrations, beachfront barbecues, rum tastings, and unforgettable dinners crafted by world-class chefs. The atmosphere is both luxurious and relaxed, with the Grand Cayman waters providing the perfect backdrop for a week of indulgence.
To help guide your culinary journey to the island, have a look at our blog covering the Best Food to Try When Visiting the Cayman Islands.
Red Sky at Night: Spring
As part of the Cayman National Festival of the Arts, Red Sky at Night is a cultural evening that brings together artists, performers, storytellers, and musicians in one event. Attendees can sample traditional Caymanian cuisine, browse handmade crafts, and enjoy live music, dance, and storytelling. The date of Red Sky at Night changes each year, but you can expect it during the spring between the months of February and April.
Coco Fest: February
Coco Fest is an annual celebration of all things coconut, one of Cayman’s most iconic natural treasures. Hosted on the grounds of Pedro St. James in February, this festival brings together local artisans who showcase the many ways to elevate the coconut. From sweet treats and savory dishes to handcrafted products and refreshing drinks, it’s a festival that celebrates the coconut’s role in Caymanian life while supporting local talent and traditions.
Cayman Carnival Batabano: First Weekend of May
One of the most anticipated events of the year is Cayman Carnival Batabano, the national carnival of the Cayman Islands. The name “Batabano” refers to the tracks left in the sand by turtles marking the beginning of nesting season — a cause for celebration!
Traditionally held on the first week of May, Seven Mile Beach and George Town come alive with elaborate costumes, pulsating rhythms, and a joyous road parade that draws both locals and visitors. If you want to see Cayman in full swing, make sure to plan your trip here around Batabano. You can also read our blog about What Time of Year is it Best to Visit Grand Cayman for more tips!
Cayman Art Week: May
Cayman Art Week shines a spotlight on the islands’ creative scene every May. Over several days, galleries, studios, and pop-up exhibitions open their doors to showcase the work of local and international artists. Visitors can wander from contemporary installations to workshops, meeting artists and collectors, and perhaps finding a piece to take home.
CayMAS Carnival: July
CayMAS Carnival offers another chance to embrace the energy of carnival season. Held over the Constitution Day weekend, CayMAS brings together masqueraders in glittering costumes, live bands, and road parades. The atmosphere is electrifying, with revelers dancing in the streets and celebrations continuing long into the night. For those who miss out on Cayman Carnival Batabano, the CayMAS Carnival offers an opportunity to still experience the festivities!
Flowers Sea Swim: June
Known as Grand Cayman’s flagship sporting event, the Flowers Sea Swim takes place along the famous Seven Mile Beach each June. Participants of all ages and abilities, from Olympic athletes to amateurs, join the one-mile swim in the crystal-clear Caribbean waters, cheered on by spectators from the shore. Beyond the athletic challenge, the event has a strong community spirit, always raising funds for charitable causes.
Pirates Week: Early to Mid-November
One of the most unique and iconic events in the Cayman Islands, Pirates Week is a celebration of the territory’s maritime heritage. Taking place every November, the event transforms the islands into a stage for swashbuckling adventures, with mock pirate invasions, parades, street dances, fireworks, and cultural displays. Each district also takes part in District Days that highlight traditional music, food, and crafts, giving visitors an authentic taste of local culture. Get your pirate hat on, as this is a festival you won’t want to miss!
Cayman Restaurant Month: October
Each October, Cayman Islands Restaurant Month invites both visitors and locals to indulge in the island’s world-class dining scene at unbeatable value. For an entire month, participating restaurants across Grand Cayman offer special prix fixe menus, giving diners the chance to sample signature dishes and explore new flavors at reduced prices. From upscale fine dining on Seven Mile Beach to casual seaside eateries, the event showcases why the Cayman Islands are known as the Culinary Capital of the Caribbean.
For tips on how to make the most of your time on the island, read our guide to What to Do and Eat on Grand Cayman for 5 Days.
Cayman Islands Marathon: Early December
Every December, runners from around the globe come to Grand Cayman for the Cayman Islands Marathon. The event includes a full marathon, half marathon, four-person relay, and a kids’ fun run, with a flat and scenic course that winds through George Town and along the coastline. With its festive atmosphere, live entertainment, and enthusiastic local support, the marathon is as much a cultural celebration as it is a sporting event.
Cayman Events Calendar
For a quick summary of everything on offer throughout the year, here is a Cayman events calendar:
- January: Cayman Cookout
- February: Coco Fest
- May: Cayman Carnival Batabano, Cayman Art Week
- June: Flowers Sea Swim
- July: CayMAS Carnival
- November: Pirates Week
- October: Cayman Restaurant Month
- December: Cayman Islands Marathon
Experience the Best of Grand Cayman with Red Sail Sports
Whether you’re dancing through the streets at Batabano, sipping fine wine at Cayman Cookout, or savoring coconut-inspired dishes at Coco Fest, Grand Cayman’s festivals offer an unparalleled way to experience the island and its culture. And at Red Sail Sports, we believe the best way to round out your festival experience is by pairing it with a day on the water!
Whichever festival or event in Grand Cayman you wish to join in, we’ll be here to help you make the most of your experience with our range of Grand Cayman Boat Tours. If you have any questions about our excursions, don’t hesitate to contact us to learn more.
