With the biggest amateur sailing prize on the East Coast up for grabs, the Antigua and Barbuda Hamptons Challenge will again take place on Saturday, August 10. This event was the brainchild of the iconic Rob Roden, founder and publisher of the Captain’s Guide, who passed away in August 2018 just weeks before the inaugural event. Carried on by his wife Theresa, the race is held on beautiful Peconic Bay at the East End of Long Island.


The 2023 Antigua and Barbuda Hamptons Challenge winners, Bill Lenhert from Cutchogue, NY with family and crew, celebrate in Antigua after winning their division in the 2024 Antigua Sailing Week.


Sponsored by the Antigua and Barbuda Tourism Board and sanctioned by the Peconic Bay Sailing Association, the event comprises a single race using PHRF of Eastern Long Island handicap ratings. Proceeds from the Antigua and Barbuda Hamptons Challenge Regatta benefits iTri Girls, a local non-profit that empowers adolescent girls through the sport of triathlon. Prizes, to be awarded at the post-race party (5:30 – 8:00 pm) in Sag Harbor, include:

· 1st Prize: Airfare, charter boat for Antigua Sailing Week 2025 (April 26 – May 2), hotel accommodations in Antigua and registration fees to compete in Antigua Sailing Week for captain and crew of five.

· 2nd Prize: Lunch for four at the American Hotel, Sag Harbor

· 3rd Prize: English Harbour Antigua Rum

· Smaller cup trophies for 1st, 2nd and 3rd place overall

· Glass plaques for 1st, 2nd and 3rd place in each division

Registration is now open and available online via Regatta Network.  ■