Vineyard Cup Regatta is a full weekend of racing, socializing, and dining to benefit Sail Martha’s Vineyard. Buoy racing for all classes is held on the waters of Nantucket Sound and Vineyard Sound. Public welcome to watch from the shore, or to get a taste of the sailing atmosphere by getting a Vineyard Cup Bracelet. At the end of each race, sailors and spectators come together to celebrate in the Race Village (hosted by the Martha’s Vineyard Shipyard) for an awards party, local food, drinks and live music. Adult passes (for those 21 and older) run $45 a day or $100 for the full three days.