Classic Beauty Returns: Vineyard Cup Set to Sail Around Martha’s Vineyard
VINEYARD HAVEN, Mass. — The 2025 Vineyard Cup sets sail this weekend, July 11–13, bringing a fleet of more than 30 classic sailing yachts to the waters surrounding Martha’s Vineyard. Organized by Sail Martha’s Vineyard (SailMV), the event marks the second stop of the summer-long Classic Yacht Challenge Series (CYCS), following the Tiedemann Regatta in Newport.
“The Vineyard Cup has become a valued addition to our summer lineup of gorgeous sailing in the Northeast,” said Timmy Dittrich, Chair of the Classic Yacht Owners Association (CYOA). Now in its second year as part of the CYCS circuit, the Vineyard Cup combines elegant racing with a community-driven cause.
Started as a way to bring large-boat racing back to Vineyard Haven and to raise funds for local maritime education, the Vineyard Cup is deeply rooted in the mission of SailMV: to perpetuate the island’s seafaring heritage while building a more inclusive and accessible future on the water.
“The aim was always to host a great regatta and to support SailMV’s efforts,” said race organizer Andrew Nutton. “It’s about fostering the Vineyard’s maritime culture while making sailing and seamanship available to all.”
Racing will take place Friday and Saturday, July 11–12, with Sunday designated as a reserve day if needed. The event will see four CRF divisions on the line, with current CYCS leaders including Gesture, Abigail, Lively Lady, and Ponyo, based on opening results from Newport.
The Vineyard Cup is more than just a regatta; it’s a celebration of tradition, education, and the enduring beauty of classic wooden and restored yachts under sail. Proceeds support SailMV’s year-round maritime programs, which include sailing instruction, boatbuilding, rowing, and marine science education for island youth.
Full regatta details and race tracking are available via the SailMV website, and CYCS results can be found at the CYOA website.
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