It’s that time of year when fun and philanthropy combine for a whirlwind of glamorous galas and social soirées in Cayman.

From black-tie affairs to stylish evenings dressed around a theme, the islands’ charitable social calendar is an opportunity to support community causes while enjoying a sensational evening out.

It’s a heady mix of Champagne receptions, dinner and dancing, live and silent auctions, entertainment and celebrity speakers.

Gala season launches at the end of September with two black-tie events – the Heart of the Jungle Masked Ball in support of the Cayman Heart Fund at the Kimpton Seafire Resort + Spa on 29 Sept. and the Cayman Islands Institute of Professional Accountants Awards Gala, also at the Kimpton, on 30 Sept. The season then swings into high gear with the following events:

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BREAST CANCER GALA DINNER

The Breast Cancer Gala Dinner in October is a highlight of Cayman’s gala season.

Held in the ballroom of The Ritz-Carlton, Grand Cayman, it is a black-tie -evening – make that pink tie – which is the main fundraising event for the Breast Cancer Foundation.

It is a highly anticipated event – this year’s gala fully sold out by July, with a 100-plus-person waiting list. Keep this in mind for the 2024 edition and book tickets early.

Funds raised help the foundation to offer physical, emotional, social, and spiritual support to breast cancer patients and their families in Cayman.

A big buzz of the event is who will be the celebrity guest speaker – with the likes of Sarah, Duchess of York, and actresses Shannen Doherty and Cynthia Nixon taking the podium in past years.

This year’s speaker is Mathew Knowles, male breast cancer survivor and father of Grammy award-winning artist Beyoncé. He will be talking about breast cancer diagnosis and early detection as well as speaking to men about the importance of early detection and testing.

The gala features a bubbly reception, three-course dinner, entertainment, dancing, and live and silent auctions.

Date: Saturday, 7 Oct.
Time: 7 p.m.
Venue: The Ritz-Carlton, Grand Cayman
Tickets: [email protected]

CCMI’S FESTIVAL OF SEAS

This year’s gala marks the Central Caribbean Marine Institute’s silver anniversary.

This milestone gala will be an elegant soiree celebrating 25 years of CCMI’s marine research. It takes place on 4 Nov. in the ballroom of the Kimpton Seafire Resort + Spa.

Guests are greeted with a Champagne reception, followed by a three-course dinner, live and online auctions, keynote address by free diver Tanya Streeter, and live music by Lionfish.

To mark the anniversary, the dress code is black-tie and ‘silver sparkle’.

Festival of Seas is CCMI’s largest fundraising event of the year, with money raised helping to support its operations, education and coral reef research programmes.

Date: Saturday, 4 Nov.
Time: 6:30 p.m.
Venue: Kimpton Seafire Resort + Spa
Tickets: [email protected]

OPEN YOUR HEARTS TO THE CHILDREN

Help for Children Cayman (formerly Hedge Funds Care Cayman) will hold its annual Open Your Hearts to the Children gala at the Kimpton Seafire Resort + Spa on 18 Nov.

The evening includes a cocktail reception, three-course dinner, live and silent auctions and live entertainment. This year’s theme: Intergalactic Black Tie.

The flagship event raised an impressive US$300,000 last year – which was dressed around a Woodstock theme – with funds supporting the non-profit organisation’s commitment to prevent, treat and end child abuse in the Cayman Islands.

Help for Children is an international charity supported largely by the financial services industry. Since its inception in 2005, the Cayman Islands chapter has raised more than US$4.5 million to help prevent and treat child abuse. Money raised stays in Cayman and benefits a variety of local initiatives.

Date: Saturday, 18 Nov.
Time: 6 p.m.
Venue: Kimpton Seafire Resort + Spa
Tickets: [email protected]

NATIONAL GALLERY COSTUME GALA

The National Gallery’s gala fundraiser is another highly anticipated event, featuring elaborate themes and costumes.

This year’s gala is set for 24 Nov. at the gallery’s outdoor gardens. Each year, guests are invited to use their imagination to engage with the annual theme. Over the years, themes have included everything from ‘Extreme Fashion’ and ‘The Night Circus’ to the ‘Surrealist Ball’ and ‘Night at the Museum’.

The imaginative décor and performances make for a memorable, fun-filled evening. Proceeds benefit the National Gallery’s education programmes and free admission to exhibitions and programming throughout the year.

Date: Saturday, 24 Nov.
Time: 6:30 p.m.
Venue: National Gallery of the Cayman Islands
Tickets: [email protected]

A SPARKLING CHRISTMAS SEASON

Gala season takes a breather once Cayman’s beloved Christmas season begins, which also features a whirlwind of events.

A gala tree lighting ceremony at Camana Bay in November kicks off the holiday season in grand style.

Other holiday highlights include the annual Rotary tree lighting ceremony in downtown George Town; Christmas at the Castle, a special evening at Pedro St. James that includes a tree lighting, carol singing and craft market; and the Mistletoe All White Christmas Party, a gala event at Abacus in Camana Bay, where revellers put on their best winter whites and dance the night away.

Cayman’s festive season is also filled with fun runs, Santa sightings, Christmas fairs, markets and bazaars, holiday concerts and parties to ring in the New Year.

Visit Compass Media’s events calendar for details of holiday happenings: compassmedia.ky/event-calendar.

This article originally appeared in What’s Hot, Autumn 2023 issue.