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A Guide To The Best Annual Events In The Cayman Islands

A Guide to the Best Annual Events in the Cayman Islands

A Guide to the Best Annual Events in the Cayman Islands

MAY 09 2025
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If you are looking for a vacation destination that could be defined as paradise on earth, you would probably find it in the Cayman Islands. During a Cayman Islands vacation, you can create memories of a lifetime.

To get the best out of your vacation, you would do well to visit the islands during some major annual events. Here, we look closely at 12 annual events in the Cayman Islands spread across the year to make your vacation most enjoyable whenever you visit.

#1 Cayman Cookout (January)

The Annual Cayman Cookout has been around for over 15 years. It is one of the most renowned culinary festivals in the world and one of the Grand Cayman events that all food lovers must attend. Held at the Ritz-Carlton, the Cayman Cookout features cooking demonstrations and wine pairings by renowned chefs and sommeliers.

#2 Agricultural Show (February-March)

If you love fresh produce and farm products, this fun-filled event held on Ash Wednesday every year is worth attending. It features various family activities, arts and crafts, and live music, along with displays of farm animals and top-quality farm produce from the island. Children and adults can engage in horse riding and animal petting activities with farm animals.

#3 Easter (April)

Easter is a favorite time for celebration during April across the Cayman Islands. On Easter Sunday there are lots of Grand Cayman events happening with church services, Easter brunches, and camping on the beach. There are even Easter Egg hunts.

#4 Batabano Carnival (May)

Batabano in May is one of the biggest annual carnivals in Caymans. It is the national carnival of the Cayman Islands featuring colorful costumes, dance, music, good food, and much gaiety.

Thousands throng to watch the parade, where participants show their creativity through elaborate costumes and floats. The word "Batabano" alludes to the turtling heritage of the Cayman Islands and the tracks that sea turtles leave behind in the sand.

#5 Flowers Sea Swim (June)

The Flowers Sea Swim, held in June, is a swimming extravaganza open to all. Whether you are an amateur or a professional swimmer, if you are on a visit to the Cayman Islands in June, do not miss this event.

There are loads of prizes to be won among the over 1,000 participants taking part in this swimming competition across the Seven-Mile Beach. Proceeds from this event are donated to local charities.

#6 Cayman Islands International Underwater Film Festival (CIUFF) and 4th of July (July)

Come July, you can attend the Cayman Islands International Underwater Film Festival (CIUFF). It is one of the most unique events in the Cayman Islands because it combines underwater films with environmental awareness.

You can see some stunning shots of aquatic life through the powerful medium of cinematography and photography. If you are in the Cayman Islands on the 4th of July, you can enjoy the fireworks and all the revelry associated with American Independence Day.    

#7 Summer Camps & Cultural Workshops (August)

During August, other than Emancipation Day, which is a day of remembrance of the enslaved people in British colonies, there are no major Grand Cayman events.

However, there are several summer camps and workshops in which kids and adults can participate to acquaint themselves with the art and culture of Caymans. You get to hear traditional Caymanian music and see local arts and crafts. Don't forget to sample the local cuisine as you go about these activities.

#8 International Scuba Diving Hall of Fame Induction Ceremony (September)

The International Scuba Diving Hall of Fame Induction Ceremony, held in September, would be delightful if you are a scuba diving enthusiast on a visit to Cayman Islands. Significant contributors to the field of scuba diving are honored on this day. The event is marked with exhibitions, dive tours, and people receive scuba diving certificates.

#9 Halloween (October)

As is the case in many parts of the world, Halloween on the last day of October is celebrated in the Cayman Islands with great pomp and gaiety. Although this is not one of the official events in the Cayman Islands, there are high levels of participation with children trick-or-treating. There are several spooky events organized where folks of all ages can participate. As the sun goes down on this day, adults join lively costume parties at nightclubs and bars with attractive prizes awarded for the best costumes.

#10 Pirates Week (November)

If you are visiting Cayman Islands during November, then Pirates Week is something you don't want to miss! Packed with pirate parades, street dancing, music, competitions, sports events, and more, you will enjoy yourself thoroughly.

And, don't miss a mock pirate invasion of the island culminating in the capturing of the Governor with pirates taking over the island! Pirates Week is generally considered the kick-off of the winter tourist season in the Cayman Islands.

#11 Cayman Islands Marathon (December)

The Cayman Islands Marathon is an event that will add excitement to your Cayman Islands vacation. You can participate in the 26.2-mile marathon individually or in a relay team. It is one of the most scenic marathon routes in the world, and the support provided is excellent. This event is usually held on the first Sunday of December.

#12 Christmas (December)

Although you won’t see any snow during December in the Cayman Islands, the magic of Christmas descends everywhere. There is much Christmas cheer going around amid balmy ocean breezes. You will see Christmas trees and decorations everywhere. You can enjoy sumptuous Christmas lunches at the various restaurants across the islands. And, don’t forget the magic of exchanging gifts over the festival!

Celebrate the Best of Cayman Islands All Year Round

From vibrant cultural festivals to world-class sporting events, the Cayman Islands offer something for everyone year-round. These 12 annual events showcase the islands’ rich heritage, lively spirit, and natural beauty.

Whether you're a foodie, music lover, or adventure seeker, there's always a reason to return and celebrate in Cayman.

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