New for 2024! Vineyard Cup has been added to the Classic Yacht Challenge Series!


Kicks off BIG BOAT RACING ON THE VINEYARD and is held on the waters of Nantucket Sound and Vineyard Sound off the Island of Martha’s Vineyard with racing on Saturday and Sunday, July 8th and 9th, 2023. Sail Martha’s Vineyard (SMV, is the Organizing Authority and invites all to come and enjoy a great blend of sailing and fun.

Proceeds from the Vineyard Cup Regatta help to support the year-round maritime programs of Sail Martha’s Vineyard.

…and while you’re in the area

Participating CYOA Yachts: 

(Click a boat to see the profile. Owners: you can update your profile under the Portal).


Thanks to our Diamond and Gold Partners

Interested in becoming a partner of the CYOA? Join as a Partner online or contact us at for details.


The Classic Yacht Owners Association is an exempt organization as described in Section 501(C) (3) of the Internal Revenue Code. Donations and membership fees are charitable contributions and tax-deductible. Employer Identification Number: 81-285925

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