Events in the Cayman Islands

The guide to family friendly events in Cayman including activities, movies, sporting events, seasonal happenings, parenting classes and more.

Featured Events

Wed 01 Oct

Cayman Restaurant Month 2025

By: Cayman Islands Tourism Association (CITA)

Celebrating the culinary capital of the Caribbean!

Participating restaurants across Grand Cayman

Sun 19 Oct

Spotlight on Memories

By: Jasmine

Memorable hits, local talent!

Harquail Theatre

Sat 25 Oct

Halloween Moonlight and Movies at Camana Bay

By: Camana Bay

7:15pm - 9:00pm

Join us at Camana Bay’s Crescent for a special screening of Disney Pixar’s Coco (PG).

The Crescent, Camana Bay

Fri 31 Oct

Twilight and Silhouettes

By: Cayman National Choir & Orchestra

From 7:30

Halloween concert: Twilight and Silhouettes with Cayman Choir and Orchestra

Located at the F. J. Harquail Cultural Centre

Sat 01 Nov

Tea & Tequila: An Afternoon Tea Fundraiser

By: Autism Cayman

2:00pm - 5:00pm

An afternoon fundraiser blending tradition, flavour, and support for Autism Cayman

Event is located at The Brasserie.

Tue 18 Nov

Bedi Walker Boarding School Fair

By: Bedi Walker

6:00pm - 8:00pm

Join the International Boarding School Fair and speak with over 40 representatives from various Junior College Prep Boarding Schools and College Prep Boarding Schools.

Marriott Resort, Seven Mile Beach

Sat 22 Nov

CI National Museum - Christmas Market & Anniversary Celebrations

By: Cayman Islands National Museum

5:00pm - 8:00pm

Shop local this Christmas with unique artisan gifts and delicious Caymanian food.

Cayman Islands National Museum, George Town

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Wed 01 Oct

Cayman Restaurant Month 2025

By: Cayman Islands Tourism Association (CITA)

Celebrating the culinary capital of the Caribbean!

Participating restaurants across Grand Cayman

Sun 19 Oct

Spotlight on Memories

By: Jasmine

Memorable hits, local talent!

Harquail Theatre

Tue 21 Oct

Community Chess, Sunset House

By: Cayman Chess Club

From 5.30pm

Join the Cayman Chess Club for a complimentary chess class and open challenges weekly. Anyone can learn, play and enjoy chess; even complete beginners.

Sunset House

Wed 22 Oct

Wednesday Night Hartley Club Sailing/Racing, CISC

By: Cayman Islands Sailing Club

4:30pm - 6:30pm

CISC would like to welcome sailors to join us for Wednesday night club sailing/racing.

Cayman Islands Sailing Club, Spinnaker Road, Red Bay

Sat 25 Oct

Wha Happening?

By: Cayman National Cultural Foundation (CNCF)

All New Cayman Comedy at its finest!

Harquail Theatre

Sat 25 Oct

Halloween Moonlight and Movies at Camana Bay

By: Camana Bay

7:15pm - 9:00pm

Join us at Camana Bay’s Crescent for a special screening of Disney Pixar’s Coco (PG).

The Crescent, Camana Bay

Sat 25 Oct

Island Spirits SEND Halloween Family Fun Day

By: Island Spirit Cayman

8:30am - 11:30am

Inclusive Halloween event with sensory-friendly activities for children with SEND

Event will be held at Dart Park

Sat 25 Oct

Kids Drop-In Glazing Session!

By: 3 Girls and a Kiln

11:00am - 2:00pm

Get your glaze on at 3GK! From 11am-2pm drop in for our glazing session!

47 South Church Street, George Town.

Sat 25 Oct

Kids Club at the Cinema, Grand Cayman

By: Culture at the Cinema

10:00am - 11:30am

Family friendly movies are shown weekly at the cinema.

Camana Bay Cinema

Sat 25 Oct

Free Admission for Residents, Cayman Islands National Museum

By: Cayman Islands National Museum

Residents can enjoy free entry to the National Museum every Saturday.

Cayman Islands National Museum, 3 Harbour Drive at Shedden Road, George Town

Tue 28 Oct

Community Chess, Sunset House

By: Cayman Chess Club

From 5.30pm

Join the Cayman Chess Club for a complimentary chess class and open challenges weekly. Anyone can learn, play and enjoy chess; even complete beginners.

Sunset House

Wed 29 Oct

Wednesday Night Hartley Club Sailing/Racing, CISC

By: Cayman Islands Sailing Club

4:30pm - 6:30pm

CISC would like to welcome sailors to join us for Wednesday night club sailing/racing.

Cayman Islands Sailing Club, Spinnaker Road, Red Bay

Fri 31 Oct

Twilight and Silhouettes

By: Cayman National Choir & Orchestra

From 7:30

Halloween concert: Twilight and Silhouettes with Cayman Choir and Orchestra

Located at the F. J. Harquail Cultural Centre

Sat 01 Nov

Festival of Seas Enchanted Masquerade of the Deep

By: Central Caribbean Marine Institute

6:30pm - 11:30pm

Celebrate the wonder and beauty of the sea while raising critical funds to protect it with CCMI!

Hotel Indigo

Sat 01 Nov

Tea & Tequila: An Afternoon Tea Fundraiser

By: Autism Cayman

2:00pm - 5:00pm

An afternoon fundraiser blending tradition, flavour, and support for Autism Cayman

Event is located at The Brasserie.

Sat 01 Nov

Kids Club at the Cinema, Grand Cayman

By: Culture at the Cinema

10:00am - 11:30am

Family friendly movies are shown weekly at the cinema.

Camana Bay Cinema

Sat 01 Nov

Free Admission for Residents, Cayman Islands National Museum

By: Cayman Islands National Museum

Residents can enjoy free entry to the National Museum every Saturday.

Cayman Islands National Museum, 3 Harbour Drive at Shedden Road, George Town

Tue 04 Nov

Community Chess, Sunset House

By: Cayman Chess Club

From 5.30pm

Join the Cayman Chess Club for a complimentary chess class and open challenges weekly. Anyone can learn, play and enjoy chess; even complete beginners.

Sunset House

Wed 05 Nov