The Classic Yacht Challenge Series Sweeps Into the Weekend With the Enthralling Vineyard Cup Regatta

The 2025 sailing season ignites grandly with the second event in the Classic Yacht Challenge Series (CYCS), the Vineyard Cup, starting this Friday, July 11. The event is significantly organized by Sail Martha’s Vineyard (SailMV), an institution dedicated to promoting Maritime culture and history in the area. The weekend regatta has garnered an impressive fleet of over 30 sailing vessels, ready to race around the scenic Martha’s Vineyard.

The Vineyard Cup was warmly welcomed into the CYCS last year, according to the CYCS Chair, Timmy Dittrich. As a premier regatta racing in the Northeast, the Vineyard Cup adds a new layer of excitement to the summer sailing season. The dual objectives of this regatta are to provide a prominent summer boat regatta for Vineyard Haven, and to fundraise for SailMV’s contributions towards the preservation of the island’s maritime history and culture.

Sail MV’s extensive programming includes the Vineyard Cup as part of its efforts to venerate and strengthen Martha’s Vineyard’s rich maritime legacy. The organization strives to promote diversity and inclusivity in the sailing, rowing, and maritime communities, making training, maritime skills, and environmental sustainability knowledge accessible to everyone.

The Vineyard Cup sets sail this Friday, July 11, continuing through Saturday. Sunday, July 13, serves as a reserve day. For information on this spectacular celebration of sailing classics and a unique blend of heritage and competition, one can visit the Sail MV website.