15th Annual Antigua & Barbuda Hamptons Challenge Celebrates Record-Breaking Weekend In Sag Harbor

The sails may have come down, but the spirit of Antigua & Barbuda remains after the 15th Annual Antigua & Barbuda Hamptons Challenge Regatta and Taste of the Caribbean Awards Party brought a record number of boats to the water of Sag Harbor and a sold-out gathering ashore for what organizers are celebrating as the event’s best year yet.

Part sailing competition, part Caribbean celebration, this year’s event marked fifteen years of bringing together the sailing communities of Sag Harbor, the East End, and Antigua & Barbuda — all in support of i-tri, the local nonprofit helping middle-school girls discover their strength, confidence, and courage through the sport of triathlon.

The day began on the water, where boats filled the bay for a spirited afternoon of racing. Sailors from throughout the region came together not only for a place on the podium, but for the opportunity to carry their journey from the waters of Sag Harbor to Antigua, with the winning team earning the opportunity to compete during Antigua Sailing Week.

Leading this year’s fleet was Glory Days, helmed by Peter Beardsley, taking 1st Overall, followed by Zorro, helmed by Rich Prieto, in 2nd Overall, and Mind Goblin, helmed by Vidar Minkovsky, taking 3rd Overall.

As the boats returned and the afternoon softened over the harbor, the celebration moved ashore for the Taste of the Caribbean Awards Party, where a sold-out crowd gathered to continue the celebration well into the evening.

The spirit of Antigua & Barbuda could be felt throughout the night, from Caribbean-inspired cuisine and the sounds of steel drums to guests filling the dance floor and dancing the night away. Sailors, residents, visitors, community supporters, and friends from Antigua & Barbuda came together beneath the energy of a Hamptons summer evening — turning the awards celebration into a true gathering of culture, joy, and community.

Between the presentation of the regatta awards, the chance auction, music, and dancing, the evening carried the warmth and rhythm of the Caribbean into Sag Harbor. For one night, two communities connected by the sea celebrated side by side a fitting close to the 15th anniversary of a tradition that continues to grow in both spirit and support.

Theresa Roden, Founder & Chief Visionary Officer of i-tri, shared, “We are thrilled by the incredible support from our sailing community here in Sag Harbor and throughout the East End. To welcome the Antigua & Barbuda community and celebrate 15 years of this annual tradition together was incredibly special. With 24 boats on the water and a sold-out celebration, this was truly our best year yet. We are so grateful to everyone who continues to show up for this event, for our community, and most importantly, for the girls of i-tri.”

For i-tri, the impact of the weekend continues long after the final sail comes down. Each registration, party ticket, chance auction entry, and contribution helps provide girls with the coaching, equipment, transportation, mentorship, and emotional support needed throughout their journey toward completing a youth-distance triathlon.