Antigua and Barbuda Hamptons Challenge Regatta Marks 16 Years in Sag Harbor

Sag Harbor event connects two historic sailing communities while raising $8,000 for East End nonprofit i-tri

SAG HARBOR, New York — The 16th Annual Antigua and Barbuda Hamptons Challenge Regatta returned to Sag Harbor, bringing Caribbean sailing culture to Long Island for a weekend of competitive racing, tourism promotion and philanthropy.

The annual event celebrates a 16-year connection between the Hamptons and Antigua and Barbuda, widely recognized for its sailing heritage and home to major international events including Antigua Sailing Week.

This year’s Hamptons Challenge was held in partnership with i-tri, an East End nonprofit that empowers young women through triathlon training, mentorship and personal development.

Leading the Antigua and Barbuda delegation was The Hon. H. Charles “Max” Fernandez, Minister of Tourism, Civil Aviation, Transportation and Investment for Antigua and Barbuda, who highlighted the historic connection between Sag Harbor and Antigua’s English Harbour.

“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. 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 weekend’s activities began with a media luncheon, where Sag Harbor Mayor Tom Gardella officially welcomed the Antigua and Barbuda delegation.

The 2026 Antigua and Barbuda Hamptons Challenge brought 23 yachts to Noyack Bay for an afternoon of racing organized by the Peconic Bay Sailing Association.

Under clear skies and favorable sailing conditions, competitors raced for the event’s signature grand prize: an all-expenses-paid trip to Antigua to compete in Antigua Sailing Week 2027, scheduled for April 21–25, 2027.

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

The winning crew will now have an opportunity to trade the waters of Long Island for the Caribbean and compete at one of Antigua and Barbuda’s best-known international sailing events.

Following the competition, sailors, tourism officials, community members and guests gathered at The Bell & Anchor for the “Taste of the Caribbean” awards celebration.

Among those attending was former Sag Harbor Mayor James Larocca.

During the celebration, the Antigua and Barbuda Tourism Authority presented a $5,000 donation to i-tri, reinforcing the Hamptons Challenge’s longstanding emphasis on giving back to the local community.

An additional $3,000 was raised for i-tri through the auction of a two-night, all-expenses-paid stay provided by Blue Waters Resort & Spa, bringing the event’s fundraising total for the nonprofit to $8,000.

Kevin Phillips, General Manager of Blue Waters Resort & Spa, participated in the event and highlighted Antigua and Barbuda’s luxury hospitality offerings through the resort experience.

Guests also experienced a taste of the twin-island destination through Caribbean-inspired cuisine, rum cocktails and music, turning the awards evening into a celebration of Antigua and Barbuda’s culture and hospitality.

For the Antigua and Barbuda Tourism Authority, the Hamptons Challenge serves both as a sporting tradition and as an opportunity to introduce the destination to sailors and travelers in the important U.S. market.

Colin C. James, CEO of the Antigua and Barbuda Tourism Authority, said the event provides a valuable platform for strengthening those relationships.

“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,” 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, travelers and tastemakers.”

The weekend also included 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 travel advisors play in connecting visitors with the destination. He emphasized the value of building tourism sales through trust, personal relationships and firsthand knowledge rather than treating travel solely as a transaction.

The advisor event complemented the regatta’s broader objective of strengthening Antigua and Barbuda’s relationships with the U.S. travel industry while highlighting the destination’s sailing, luxury hospitality, culture and experiential tourism offerings.

Now in its 16th year, the Antigua and Barbuda Hamptons Challenge has developed into a distinctive bridge between two communities with deep maritime traditions.

From the sailing waters surrounding Sag Harbor to the historic English Harbour in Antigua, the event combines competitive sport with tourism, community engagement and philanthropy.

As the 2026 celebration concluded in Sag Harbor, sailors, tourism professionals and guests marked 16 years of competition, camaraderie and Caribbean culture — while looking ahead to Antigua Sailing Week 2027 and the next chapter of the relationship between Long Island and Antigua and Barbuda.

Antigua and Barbuda is a twin-island Caribbean destination known for its beaches, sailing heritage, historic sites, resorts and maritime culture. Antigua’s English Harbour and Nelson’s Dockyard are among the destination’s best-known attractions, while international sailing events continue to play a central role in the country’s tourism identity.

Antigua Sailing Week 2027: April 21–25, 2027 www.visitantiguabarbuda.com

Reporting originally appeared via eTurboNews. Read the full source for additional context.