The 16th Annual Antigua and Barbuda Hamptons Challenge Regatta returned to Sag Harbor, bringing the excitement of Caribbean sailing to Long Island while celebrating the longstanding relationship between the two maritime communities.

Antigua and Barbuda, widely recognised as the sailing capital of the Caribbean, hosted the event in partnership with i-tri, a nonprofit organisation that empowers young women across the East End of Long Island through triathlon training, mentorship and personal development.

Minister of Tourism, Civil Aviation, Transportation and Investment Charles “Max” Fernandez led the Antigua and Barbuda delegation.

“This regatta is about far more than sailing,” Fernandez said. “It reflects the longstanding maritime and cultural connections between Sag Harbor and Antigua’s historic English Harbour.”

He said both communities share a rich seafaring heritage, while the annual event helps to preserve that history, forge meaningful relationships and support the development of young people through sport.

The activities began with a media luncheon, during which Sag Harbor Mayor Tom Gardella officially welcomed the Antigua and Barbuda delegation.

Later, 23 yachts took to Noyack Bay for an afternoon of spirited competition organised by the Peconic Bay Sailing Association.

Sailors competed under clear skies and favourable conditions for the grand prize: an all-expenses-paid trip to Antigua and Barbuda to participate in Antigua Sailing Week 2027, scheduled for April 21–25.

Glory Days, helmed by Peter Beardsley, captured first place overall. Zorro, helmed by Rich Prieto, placed second, while Mind Goblin, helmed by Vidar Minkovsky, secured third place.

The competition culminated with a “Taste of the Caribbean” awards celebration at The Bell & Anchor. The event attracted sailing enthusiasts, community members, local dignitaries and other special guests, including former Sag Harbor Mayor James Larocca.