Events

T-shirt Competition

Pirates Week 2025 T-shirt Design Competition Artists of all ages are encouraged to submit an original design that captures the spirit of Pirates Week 2025.

The winning design will be featured on all official Pirates Week 2025 T-shirts, which will be available for purchase by the public during the festival.


District Heritage Costume Competition

Young Caymanians aged 17–25 are invited to vie for the honour of being the face of Caymanian pride. Contestants must demonstrate knowledge of Caymanian culture and heritage, strong communication skills, and community spirit while competing in an interview, cultural dress segment, and onstage question-and-answer segment.

Upcoming Activities

Nov
10

George Town District Day

Grand Cayman
10 November 2026
11:00 AM - 11:00 PM

11:00 a.m. Local artifacts, heritage exhibits and traditional Caymanian music, Scranton Park

11:30a.m. | Official Opening Ceremony

12:00p.m. | Heritage Judging Competition

12:30p.m. | Dream Chasers Cayman

1:00p.m. | Cultural Dance Performance

2:00p.m. | UCCI Dancers

3:00p.m. | Hula Hoop Contest

4:00p.m. | Comedy Performance

4:30p.m. | DJ & Dance Competition

5:00p.m. | Watermelon & Banana Eating Contest

5:45p.m. | Best Dressed Pirate Awards

6:00p.m. Cultural Fashion Showcase

6:30p.m. | Heritage Prize Giving

7:00p.m. | Live Entertainment

8:00p.m. | Fireworks

9:30p.m. | Yung Bredda

People, Communities & Living
Pirates Week
Nov
11

Bodden Town District Day

Grand Cayman
11 November 2026
11:00 AM - 11:00 PM

7:45p.m. | DJ Fross

8:00p.m. | Fireworks

9:30p.m. | Kerwin Du Bois

10:30p.m. | DJ Fross

People, Communities & Living
Pirates Week
Nov
12

West Bay District Day

Grand Cayman
12 November 2026
11:00 AM - 11:00 PM

11:00a.m. | Official Opening

West Bay Heritage Site, next to Ed Bush Stadium.

Welcome, prayer, "Beloved Isle Cayman" and the blowing of the conch shell

All day | Arts, Crafts & Local Food

Silver Thatch Ladies, rope making, conch shells and gigs, plus seafood, local dishes, roasted fish and sweet treats

All day | Heritage Activities

Artifact display, educational tours, domino games and DJ music

All day | Kids' Activities

Baby show, games and contests

People, Communities & Living
Pirates Week
Nov
13

East End District Day

Grand Cayman
13 November 2026
11:00 AM - 11:00 PM

11:00a.m.| Gates Open at Heritage Site, with welcome music and displays

11:30a.m. | Official Opening Ceremony, Food service begins

12:30p.m. Cultural Performance School children from East End Primary School

2:00p.m. | Heritage Trivia

3:00p.m. - 4:00p.m. | Pirates Landing

8:00p.m. | Fireworks

9:30p.m. | Lyrikal & Nadia Batson

Join the district celebrations

All day: roasting corn, fry fish, rope making and thatch plaiting demos, antiques on display, and live music from local and international artists!

People, Communities & Living
Pirates Week
Nov
14

5k Sea Swim

Grand Cayman
14 November 2026
7:00 AM - 10:00 AM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Closing Fireworks

Grand Cayman
14 November 2026
8:00 AM - 8:20 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Food Festival

Grand Cayman
14 November 2026
3:00 PM - 3:00 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Children’s Play Area

Grand Cayman
14 November 2026
3:30 PM - 7:00 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Jr. Snapper Cook-Off Contest

Grand Cayman
14 November 2026
3:30 PM - 5:30 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Dance Demo

Grand Cayman
14 November 2026
4:00 PM - 4:30 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Water Mermaids Showcase

Grand Cayman
14 November 2026

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Trial of the Pirates

Grand Cayman
14 November 2026
5:00 PM - 5:00 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
14

Grand Finale Street Dance

Grand Cayman
14 November 2026
7:00 PM - 11:30 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
20

Pirates Landing

Little Cayman
20 November 2026
5:00 PM - 5:00 PM

Details to be announced.

People, Communities & Living
Pirates Week
Nov
20

Live Band

Little Cayman
20 November 2026
6:00 PM - 10:00 PM
TBC

Details to be announced.

People, Communities & Living
Pirates Week
Nov
20

Fireworks

Little Cayman
20 November 2026
8:00 PM - 8:00 PM
TBC

Details to be announced.

People, Communities & Living
Pirates Week
Nov
21

Pirates Pub Crawl and after-party

Little Cayman
21 November 2026
6:00 PM - 12:00 AM

Details to be announced.

People, Communities & Living
Pirates Week
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