Antigua and Barbuda’s Hamptons Challenge Regatta Strengthens 16-Year Maritime Partnership

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.

During the ceremony, the Antigua and Barbuda Tourism Authority presented a US$5,000 donation to i-tri.

An auction featuring a two-night, all-expenses-paid stay at Blue Waters Resort and Spa raised an additional US$3,000 for the organisation. The resort was represented by its general manager, Kevin Phillips, who also promoted Antigua and Barbuda’s luxury accommodation and visitor experiences.

Chief Executive Officer of the Antigua and Barbuda Tourism Authority Colin C. James said the regatta remains an important part of the country’s tourism marketing strategy.

“The Hamptons Challenge not only promotes Antigua and Barbuda as a premier sailing destination, but also enables us to connect directly with travellers who appreciate culture, community and world-class experiences,” James said.

“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, travellers and tastemakers.”

Guests at the celebration were treated to Caribbean-inspired cuisine, rum cocktails and music, transforming the evening into a showcase of Antigua and Barbuda’s culture and hospitality.

The weekend also included a VIP luncheon for Long Island travel advisors hosted by the Tourism Authority.

Antigua and Barbuda’s United States Director of Tourism Dean Fenton recognised the important role travel advisors play in connecting visitors with the destination. He stressed that successful sales relationships are built on trust and meaningful personal connections rather than transactions alone.

Now in its 16th year, the Hamptons Challenge continues to strengthen the bond between Sag Harbor and Antigua and Barbuda’s historic English Harbour.

The event ended with sailors, tourism professionals and guests celebrating 16 years of competition, camaraderie, philanthropy and Caribbean culture.