More than 85 sailboats registered for the 15th annual event, which carries cruisers and racers alike from Norfolk to Cape Charles and back during the two-day race.
Festivities begin Friday before the race with a skippers’ meeting complete with a barbecue dinner, beer and live music at Bay Point Marina, in Norfolk. On Saturday, rolling starts launch from Norfolk’s Little Creek and crews race to Cape Charles, on Virginia’s Eastern Shore.
Saturday night, hundreds gather on Cape Charles’ docks for an awards ceremony and afterparty before racing back to mainland Virginia the next day.
With the regatta’s growing popularity, sponsorship dollars surpassed costs of hosting the event.
Each year, the cup helps fund the nonprofit program, which helps underserved youth in Hampton Roads get on the water to learn about science and develop skills from swimming and first aid to teamwork, leadership and communication through sailing.
Cape Charles resident Brooke Ambrose, who participated in the race, provided the following photo set: