The 16th Annual Antigua and Barbuda Hamptons Challenge Regatta returned to Sag Harbor, bringing the competitive spirit of Caribbean sailing to Long Island and celebrating a remarkable 16-year connection between the Hamptons and Antigua and Barbuda.
Antigua and Barbuda, recognized as the Caribbean’s sailing capital, hosted this celebrated regatta in partnership with i-tri, a local nonprofit dedicated to empowering young women across the East End of Long Island through triathlon training and mentorship and personal development.
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The Hon. H. Charles ‘Max’ Fernandez, Minister of Tourism, Civil Aviation, Transportation, and Investment for Antigua and Barbuda, leading the Antigua delegation, said, “This regatta is about far more than sailing. It reflects the longstanding maritime and cultural connections between Sag Harbor and Antigua’s historic English Harbour. Both communities share a rich seafaring heritage, and this annual event brings that history to life while creating meaningful connections and supporting youth development through sport.”
The activities began with a media luncheon, during which the Mayor of Sag Harbor, Hon. Tom Gardella, officially welcomed the Antigua delegation.
The annual Antigua and Barbuda Hamptons Challenge Regatta brought 23 yachts to Noyack Bay for an afternoon of spirited competition organized by the Peconic Bay Sailing Association. Under clear skies and near-perfect conditions, sailors competed for the coveted grand prize: an all-expenses-paid trip to Antigua to race in Antigua Sailing Week 2027, April 21–25 (www.sailingweek.com), one of the Caribbean’s premier international sailing events. The “Taste of the Caribbean” Awards Celebration at Bell & Anchor, a popular local restaurant with a diverse audience, including sailing enthusiasts, local dignitaries, community members, and special guests, including the former Sag Harbor Mayor James Larocca.
Leading this year’s fleet was Glory Days, helmed by Peter Beardsley, taking 1st Overall, followed by Zorro, helmed by Rich Prieto, in 2nd Overall, and Mind Goblin, helmed by Vidar Minkovsky, taking 3rd Overall. The competition culminated in an elegant awards celebration at The Bell & Anchor, where the winning crew was honored, and the Antigua and Barbuda Tourism Authority presented a $5,000 donation to i-tri.
Colin C. James, CEO of the Antigua and Barbuda Tourism Authority, highlighted the event’s significance to the island’s tourism strategy: “The Hamptons Challenge not only promotes Antigua and Barbuda as a premier sailing destination but also enables us to connect directly with travelers who appreciate culture, community, and world-class experiences. It’s always a privilege to bring a piece of Antigua to the Hamptons. The regatta gives us an extraordinary platform to showcase Antigua and Barbuda to an influential audience of sailors, travelers, and tastemakers.”
Kevin Phillips, General Manager, Blue Waters Resort & Spa, also participated, showcasing the breadth of Antigua and Barbuda’s luxury accommodation and experiential offerings by providing a 2-night, all-expenses-paid trip to the resort for auction. Raising an additional $3,000.00 for i-tri.
Guests at the awards gala experienced a taste of Antigua and Barbuda through Caribbean-inspired cuisine, rum cocktails and music, transforming the evening into an island celebration.
The weekend also featured a VIP luncheon for Long Island travel advisors hosted by the Antigua and Barbuda Tourism Authority. Dean Fenton, U.S. Director of Tourism for Antigua and Barbuda, recognized the important role advisors play in connecting travelers with the destination, emphasizing that the strongest sales relationships are built on trust and personal connections, not simply transactions.
The 16th anniversary of the Hamptons Challenge underscores the enduring connection between two celebrated maritime communities. From Sag Harbor’s sailing waters to English Harbour’s historic harbor, the event continues to build a bridge between Long Island and Antigua and Barbuda – one race, one relationship, and one Caribbean experience at a time.
As the sun set over Sag Harbor, sailors, travel professionals, and guests raised a glass to 16 years of competition, camaraderie, philanthropy, and Caribbean flair, and to a partnership whose influence continues to grow.
