12 awarded @10th Caribbean POSH Weekend Awards
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.
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7 Responses to “12 awarded @10th Caribbean POSH Weekend Awards”
The Porsh is nonesense.
Now, while I truly appreciate the purpose behind this event, I do think there's room for improvement. Speaking from personal experience, I've attended the event and I honestly didn't feel comfortable. The women at my table and the event came across as distant and somewhat unapproachable. Of course, I understand that everyone has different personalities and one experience doesn't define everyone. Still, there was an undeniable sense of stuffiness that made it difficult to relax and connect. The atmosphere felt more exclusive than inclusive. My biggest concern is that the event can unintentionally come across as being geared toward a more upper-class crowd, which may discourage women from different backgrounds from attending or feeling like they belong. The good news is that I believe a few thoughtful changes could make a significant difference.
For example, having table hosts and simple icebreaker activities could help guests introduce themselves and feel more at ease, especially if they're attending alone or sitting with strangers. It's a small touch that could spark genuine conversations and new friendships. I'd also love to see more speakers share authentic stories not just their successes but also their struggles, setbacks and lessons learned along the way. People often connect more with authencity than perfection. Hearing how someone overcame challenges can be just as inspiring as hearing about their achievements.
I also think it would be refreshing to celebrate more diversity by highlighting women from different family situations, income levels and life experiences. Success looks different for everyone and recognizing a wider range of journeys would allow more women to see themselves reflected in the event and feel that they truly belong.
Another idea would be to encourage conversation over networking. Too often, networking can feel like a room full of people sizing each other up. Instead, creating opportunities for meaningful dialogue shifts the focus from status to connection. That's where real community begins.
At the end of the day, an event can still be elegant, well-organised and beautifully executed without feeling “stuffy”. The events people remember most aren't necessarily the ones with the fanciest decor or the most impressive guest list. They're the ones where they felt welcomed, included and comfortable enough to be themselves.
When people truly feel like they belong, the event naturally becomes more inviting to women from every walk of life. After all, the strongest communities are built on connection, inclusion and belonging.