Caribbean Spirit Sets Sail at 15th Antigua and Barbuda Hamptons Challenge

Sag Harbor’s waters came alive on Saturday as the 15th Annual Antigua and Barbuda Hamptons Challenge Regatta brought together competitive sailing, Caribbean hospitality, and a dash of philanthropy.

Under flawless summer skies, crews from across the region battled for the grand prize, an all-expenses-paid trip to Antigua to race in the 2026 Antigua Sailing Week. After years of trying, skipper Lee Oldak finally claimed the title aboard Purple Haze, marking his first victory in the event’s history.

“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 Tourism Minister Charles Fernandez, noting the shared maritime heritage between the two ports.

The Antigua and Barbuda Tourism Authority (ABTA) used the occasion to support the host community, donating $5,000 to i-tri, a local nonprofit that mentors middle school girls through triathlon training. The gesture underscored the event’s growing reputation for blending sport with community impact.

An evening awards gala at The Bell and Anchor transformed the harbor into a slice of the Caribbean, with island-inspired cuisine, rum cocktails, and music setting the tone. ABTA CEO Colin C. James described the Challenge as “a platform to connect with travelers who value culture, community, and world-class experiences.”

The weekend also served as a networking opportunity for the islands’ tourism sector. At a VIP luncheon for travel advisors, ABTA’s U.S. Director Dean Fenton highlighted the power of personal relationships in the travel industry. Representatives from The Hut on Little Jumby Island and Blue Waters Resort & Spa shared stories of Antigua’s luxury offerings with invited guests and media.

As the sun set over Sag Harbor, sailors, dignitaries, and guests toasted not just the day’s winners, but a tradition that has grown into one of the Northeast’s most distinctive regattas, one where competition meets culture, and every finish line leads back to the warm shores of Antigua and Barbuda.