Vineyard Cup Regatta

Each July, scores of sailboats dot the waters surrounding Martha’s Vineyard. It’s a welcomed sight, rooted in the preservation and continued education of the rich maritime tradition of sailing, and is known as the Vineyard Cup Regatta. Established in 2006, the annual race is a fundraiser for the sailing program known as Sail Martha’s Vineyard (Sail MV).

Founded in 1992, Sail MV offers sailing lessons and programs that focus on the preservation of the history and culture of Martha’s Vineyard. With over 600 children and 500 adults enrolled in its annual program, Sail MV has something for everyone of all ages and levels. To help fund their programming, Sail MV created the Regatta.

Each year, the Regatta kicks off with an annual seafood dinner and auction benefit. Over the three-day event, competitors unfurl their sails and spectators enjoy the races from ashore. At the end of the races, an after party at the Race Village invites attendees to enjoy food and drink, music, and award ceremonies.

Known as a popular summer destination, the island of Martha’s Vineyard holds a rich history with deep ties to the ocean. Summer residences on the island have been documented as early as 1872 and the Island can only be accessed by boat or plane. Throughout the years, celebrities, politicians and well known individuals have spent their vacations at the Vineyard.

The Vineyard Cup Regatta is a way to embrace the island’s sailing traditions and shape the skills of future sailors. Although the Regatta was cancelled in 2020 due to a global health pandemic, Sail MV remains committed to their mission of protecting and preserving the Island’s maritime heritage.