Antigua and Barbuda Hamptons Challenge Marks 15th Year With Racing, Philanthropy, and Caribbean Flair

The 15th Annual Antigua and Barbuda Hamptons Challenge Regatta set sail last week, bringing the vibrant spirit of the Caribbean to Long Island’s shores. Held in Sag Harbor, the race drew a competitive fleet of sailors vying for the grand prize: an all-expenses-paid trip to Antigua to compete in Antigua Sailing Week 2026.

Under clear skies and near-perfect summer conditions, the event culminated in an elegant awards gala at The Bell and Anchor. In addition to celebrating the winning crew, the Antigua and Barbuda Tourism Authority presented a $5,000 donation to i-tri, a local nonprofit that empowers middle school girls through triathlon training and mentorship.

“This regatta is more than just a race — it’s a celebration of the deep historical and cultural ties between Sag Harbor and English Harbour in Antigua,” said Charles Fernandez, Antigua and Barbuda’s Minister of Tourism, Civil Aviation, Transportation and Investment. “Both harbours are rich in maritime heritage, and this annual event beautifully showcases that connection while also building bridges between our communities.”

The Hamptons Challenge has become one of the most anticipated regattas in the Northeast, blending top-tier sailing with philanthropy and Antiguan hospitality

“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,” said Colin C. James, CEO of the Antigua and Barbuda Tourism Authority.

Guests at the gala enjoyed Caribbean-inspired cuisine, rum cocktails and music, evoking the warmth and vibrancy of Antigua and Barbuda.

The winning skipper, Lee Oldak, who has raced every year since the regatta’s inception, finally claimed victory aboard “Purple Haze” on his 15th attempt. He and his crew will now head to Antigua for one of the world’s most prestigious sailing events.

The weekend also included a VIP lunch for Long Island travel advisors, hosted by the Antigua and Barbuda Tourism Authority. U.S. Director Dean Fenton praised advisors for their role in promoting the destination, emphasizing that “the strongest sales are built on relationships, not just transactions.”

Representatives from The Hut on Little Jumby Island and Blue Waters Resort & Spa were also on hand to share stories of Antigua and Barbuda’s luxury offerings.

As the sun set over Sag Harbor, sailors and guests toasted another successful year of competition, camaraderie and cultural exchange — further solidifying the Antigua and Barbuda Hamptons Challenge as a tradition with growing influence