Vineyard Cup Regatta is a full weekend of racing, socializing, and dining to benefit Sail Martha’s Vineyard. Friday & Saturday, July 10 & 11, 2026, with Sunday the 12th as a reserve day. 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.
Race Party at Sail MV Boathouse, Sail Camp Park, 177 Barnes Road, Oak Bluffs, MA 02557. Food and refreshments will be served. A $35 per person donation is suggested and may be paid at the event. Accessible by small, beachable boat via Lagoon Pond.)