The 2026 ICON Woman honorees include the Honourable Cora Richardson-Hodge, Premier of Anguilla; Dr. Legena Henry, Founder and CEO of Rum & Sargassum; Dona Regis-Prosper, Secretary-General and CEO of the Caribbean Tourism Organization; Jennifer Matarangas-King, Commissioner of the U.S. Virgin Islands Department of Tourism; Hilma Roebuck, Owner and Operating Manager of 101.3 ROEFM WEVI; and Lynette Harrigan, MBE, Niche Marketing and Tourism Liaison Manager with the BVI Tourist Board. Photo: Facebook

Six other outstanding women were recognized during the 10th Edition of Caribbean POSH Weekend, The Awardees were Jemmeni Dionné Moore of the U.S. Virgin Islands, who received the Entrepreneurial Excellence Award, and Dr. Karen M. Carty, also from the U.S. Virgin Islands, who was presented with the Sports Excellence Award for her significant contributions. Representing St. Maarten, Clara Reyes received the Community & Culture Award, while Shanda Webster-Glasgow, originally from St. Maarten and now residing in the British Virgin Islands, earned the Culinary Excellence Award for her remarkable achievements in the culinary arts. The Empowerment Award was presented to Saelese Haynes of Trinidad and Tobago, recognizing her commitment to inspiring and uplifting others throughout the Caribbean. Photo: Facebook

Despite the glamour and celebration that define the 10th Anniversary Caribbean POSH Weekend Awards aboard Ocean 7 at Peter Island, founder Janet R. Brin revealed that organizing this year's milestone event was the organization's greatest challenge to date. Photo: Facebook

These awards celebrate visionary women whose leadership, innovation, and service continue to shape the future of the Caribbean.

2026 ICON Women Honorees 

The 2026 ICON Woman honorees include the Honourable Cora Richardson-Hodge, Premier of Anguilla; Dr Legena Henry, Founder and CEO of Rum & Sargassum; Dona Regis-Prosper, Secretary-General and CEO of the Caribbean Tourism Organisation; Jennifer Matarangas-King, Commissioner of the U.S. Virgin Islands Department of Tourism; Hilma Roebuck, Owner and Operating Manager of 101.3 ROEFM WEVI; and Lynette Harrigan, MBE, Niche Marketing and Tourism Liaison Manager with the BVI Tourist Board.

According to JTV Channel 55, “Each woman was recognised for her outstanding contributions in public service, tourism, sustainability, entrepreneurship, media and community development, reflecting the diversity and strength of female leadership across the region.”

The ICON Woman Awards continue to honour Caribbean women who are breaking barriers, creating opportunities, and inspiring the next generation of leaders while leaving a lasting legacy throughout the region.

Other awards presented @ Caribbean POSH Weekend

Additionally, six other outstanding women were recognised during the 10th Edition of Caribbean POSH Weekend, where winners were selected through a combination of public voting and expert judging.

The milestone event celebrated women whose leadership, talent, and service continue to make a lasting impact across the region. Awardees include Jemmeni Dionné Moore of the U.S. Virgin Islands, who received the Entrepreneurial Excellence Award, and Dr Karen M. Carty, also from the U.S. Virgin Islands, who was presented with the Sports Excellence Award for her significant contributions.

Representing St. Maarten, Clara Reyes received the Community & Culture Award, while Shanda Webster-Glasgow, originally from St. Maarten and now residing in the British Virgin Islands, earned the Culinary Excellence Award for her remarkable achievements in the culinary arts.

The Empowerment Award was presented to Saelese Haynes of Trinidad and Tobago, recognising her commitment to inspiring and uplifting others throughout the Caribbean.

This year's organisation was challenged 

Despite the glamour and celebration that defined the 10th Anniversary Caribbean POSH Weekend Awards aboard Ocean 7 at Peter Island, founder Janet R. Brin revealed that organising this year's milestone event was the organisation's greatest challenge to date.

"The 10th anniversary was the most challenging to pull off. We faced obstacles at almost every turn. Venues said no, financial support was limited, and there were moments when it seemed much easier to postpone than to press forward," she said.

Despite these setbacks, Brin noted that perseverance, faith, and the unwavering support of partners, volunteers, and the Caribbean POSH community made the celebration possible, adding even more meaning to the milestone.