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Welcome to the Cayman Islands – an island paradise like no other! With its turquoise waters and white sandy beaches, the Cayman Islands offer a variety of activities and attractions to make your stay unforgettable.

We invite you to join us for the top 20 annual events in the Cayman Islands. From the Cayman Islands Sea Swim to Pirates Week and Mardi Gras, there’s something for everyone. These dates and even the events will definitely change year to year, please confirm ahead of booking a unit that the event you plan to attend is scheduled.

1. Cayman Islands Sea Swim – June: Take part in the most popular open water swim in the Caribbean. The course takes you along Seven Mile Beach, with a finish (or start, depending on weather) line at the famous Ritz-Carlton. 

2. Pirates Week – November: Celebrate the legacy of the Caribbean’s most notorious characters with a full week of activities, including a parade, street festival, music, and more. 

3. Mardi Gras – February: Party your way through Grand Cayman’s streets, with a parade and festivities including masks, costumes, and live music.

4. Cayman Cookout – January: Join world-renowned chefs and mixologists for four days of cooking demonstrations, wine tastings, and more. 

5. Cayman Islands Marathon – December: Take on the 26.2-mile challenge and run through the islands’ stunning scenery. 

6. Cayman Islands International Film Festival – February: Enjoy a week of screenings and events, featuring some of the best independent films from around the world.

7. Cayman Islands Music & Heritage Festival – April: Celebrate the islands’ culture and history with live performances, exhibitions, and more.

8. Cayman Islands National Arts & Crafts Festival – May: Get a chance to meet local artisans and experience the islands’ unique art and culture.

9. Cayman Islands Triathlon – April: Test your endurance with a course that takes you through the islands’ beautiful landscapes. 

10. Cayman Islands International Literary Festival – October: Listen to renowned authors, publishers, and writers from around the world, as they share their stories and experiences.

11. Cayman Islands Jazz Festival – November: Enjoy a weekend of jazz music from some of the top jazz artists.

12. Cayman Islands Food & Wine Festival – November: Sample the islands’ best cuisine, accompanied by a selection of fine wines.

13. Cayman Islands International Boat Show – January: Get a chance to explore the islands’ nautical lifestyle, with a variety of vessels on display.

14. Cayman Islands Water Sports Festival – April: Experience the fun and excitement of watersports, with a range of activities and competitions.

15. Cayman Islands Gourmet Food Festival – June: Enjoy the best culinary experiences from the islands’ top chefs and restaurants.

16. Cayman Islands International Film Festival – May: Experience the best of Caribbean cinema, with screenings, workshops, and special events.

17. Cayman Islands International Music Festival – August: Enjoy a two-day celebration of music from around the world.

18. Cayman Islands International Scuba Diving Festival – December: Take part in a variety of diving activities, and explore the depths of the Caribbean Sea.

19. Cayman Islands International Air Show – October: Witness some of the world’s most impressive aerobatic displays, with a range of aircraft on show. 

20. Cayman Islands International Reggae Festival – December: Dance to the beats of the Caribbean, with a celebration of reggae music and culture.

So come and join us in the Cayman Islands for a truly unique and unforgettable experience.

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