Cayman’s gala season is in full swing, offering a mix of elegance and philanthropy to support various charitable causes while enjoying glamorous evenings out. From black-tie events to themed soirĂ©es, the social calendar includes Champagne receptions, dinner, dancing, live and silent auctions, entertainment, and celebrity speakers.

The gala season commenced with two black-tie events: the Heart of the Jungle Masked Ball and the Cayman Islands Institute of Professional Accountants Awards Gala. Upcoming events include:

1. Breast Cancer Gala Dinner

Mathew Knowles
  • Date: Saturday, 7 Oct.
  • Venue: The Ritz-Carlton, Grand Cayman
  • Highlights: This black-tie event is the main fundraiser for the Breast Cancer Foundation, featuring a celebrity guest speaker, Mathew Knowles, a three-course dinner, entertainment, and auctions.
  • Purpose: Funds raised support breast cancer patients and their families in Cayman.





2. CCMI’s Festival of Seas

  • Date: Saturday, 4 Nov.
  • Venue: Kimpton Seafire Resort + Spa
  • Highlights: The event celebrates the Central Caribbean Marine Institute’s 25th anniversary with a Champagne reception, three-course dinner, auctions, a keynote address by free diver Tanya Streeter, and live music.
  • Purpose: Funds raised support marine research, education, and coral reef programs.




3. Open Your Hearts to the Children

  • Date: Saturday, 18 Nov.
  • Venue: Kimpton Seafire Resort + Spa
  • Highlights: The gala features a cocktail reception, three-course dinner, live and silent auctions, and live entertainment. The theme for this year is “Intergalactic Black Tie.”
  • Purpose: The event supports Help for Children Cayman in its efforts to prevent, treat, and end child abuse in the Cayman Islands.

4. National Gallery Costume Gala

  • Date: Saturday, 24 Nov.
  • Venue: National Gallery of the Cayman Islands
  • Highlights: The gala is known for its imaginative themes and costumes, offering a fun-filled evening. Proceeds benefit the National Gallery’s education programs and free admission to exhibitions.
  • Purpose: Funds raised support the National Gallery’s artistic initiatives.

Gala season is followed by Cayman’s festive Christmas season, which includes tree-lighting ceremonies, holiday concerts, Santa sightings, Christmas fairs, markets, and New Year’s celebrations.


For more details on holiday events, visit Compass Media’s events calendar at