Against the tropical backdrop of the British Virgin Islands, the 10th annual Caribbean POSH Weekend culminated in the 2026 ICON Woman Awards, a landmark celebration honoring 15 outstanding women from seven Caribbean territories for their transformative work in leadership, entrepreneurship, and community advancement.
Centered on the theme “The Future of the Caribbean: Connection, Collaboration & Growth,” the multi-day gathering brought together a diverse cross-section of stakeholders: local and diaspora entrepreneurs, senior government officials, tourism industry leaders, creative professionals, and community organizers. Beyond the awards ceremony, the weekend featured a full schedule of intentional engagement, from targeted networking sessions and forward-focused leadership panel discussions to immersive cultural experiences that highlighted the region’s rich heritage, all designed to strengthen ties across Caribbean communities.
This year’s award cohort hails from Trinidad and Tobago, Jamaica, St. Maarten, the U.S. Virgin Islands, St. Kitts and Nevis, The Bahamas, and the British Virgin Islands, with achievements recognized across 15 distinct sectors spanning entrepreneurship, education, public health advocacy, youth leadership, fashion, digital innovation, wellness, film, sports, culture, culinary arts, performing arts, and community development. Trinidad and Tobago emerged as the most represented territory, claiming seven of the 15 available awards.
In a supplementary honor spotlighting longstanding regional impact, six distinguished senior leaders were also recognized for their decades of contribution to Caribbean progress. The honorees included Anguilla Premier Cora Richardson-Hodge; 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 at the BVI Tourist Board. Premier Richardson-Hodge delivered the event’s keynote address, centering her remarks on the urgent need for visionary leadership, cross-regional cooperation, and intentional investment in opportunities for the next generation of Caribbean women leaders.
As the awards program marks its 10th year of operation, organizers emphasize that its core mission extends far beyond a single annual celebration: to elevate women leaders whose contributions have long gone unrecognized across the region, and to nurture emerging female leaders who will shape the Caribbean’s future. “This year’s awards were a powerful reminder of the extraordinary women who continue to shape the future of the Caribbean,” shared Janette Brin, Founder and CEO of Caribbean POSH. “For ten years, Caribbean POSH has been committed to celebrating women whose leadership often goes unrecognized. Every winner represents courage, resilience, innovation, and service, and together they remind us that Caribbean excellence knows no borders.”
Caribbean POSH has evolved dramatically since its origins as a small print publication, growing into a comprehensive regional platform dedicated to amplifying Caribbean women through intentional storytelling, leadership development, formal recognition programs, and professional networking infrastructure. Additional signature events held during the 10th anniversary weekend included the POSHgirl POWER Brunch, the PINK Sunday Sunset Sail, and collaborative working sessions focused on building long-term cross-territory partnerships.
“As we celebrate ten years of Caribbean POSH, we are incredibly proud of the community we have built,” Brin added. “Our mission has always been bigger than an awards programme. It’s about creating a movement that celebrates Caribbean women, amplifies their stories, builds meaningful regional relationships, and ensures their contributions are recognized both throughout the Caribbean and around the world.”
Looking ahead, Caribbean POSH has laid out plans to expand access to collaborative opportunities for women across the region, doubling down on its commitment to fostering a more connected, inclusive, and prosperous Caribbean that centers the leadership of women.