Classic Yachts Challenge Series

The organizing authority (OA) for the Classic Yachts Challenge Series (CYCS) is the Classic Yacht Owners Association (CYOA) in cooperation with the Organizing Authorities of the participating Series Events.

Vineyard Cup

Vineyard Haven, MA

In 2024, the Vineyard Cup was 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, www.sailmv.org) is […]

Camden Classics Cup

Camden, ME

The must-not-miss event of the season with two days of racing around Penobscot Bay and amazing social events onshore hosted by Lyman Morse.

Castine Classic Yacht Race

Castine Yacht Club

The first of the three distance races in a row sends the fleet from Castine to Camden.

Camden to Brooklin Race

Castine Yacht Club

The second of the three distance races held in a weekend sends the fleet from Camden to Brooklin ahead of ERR.

Eggemoggin Reach Regatta

Brooklin, ME

The infamous wooden boat race is the largest of the season and sends the fleet west to Castine from Brooklin.

Corinthian Classic Yacht Regatta

Marblehead, MA

Kicking off the Massachusetts regattas, Corinthian Yacht Club hosts pursuit races over 2 days.

Nantucket Regatta

Nantucket, MA

Leading into the Opera House Cup, this Friday/Saturday event features buoy and distance racing.

Opera House Cup

Nantucket, MA

This event in its 53rd year the season highlight for this region. The pursuit race is followed by a parade and biggest social of the year.

Herreshoff Classic Yacht Regatta

Marblehead, MA

Featuring feeder races to and from Newport, the regatta takes place on Saturday followed by awards at the Herreshoff Marine Museum.

Thanks to our Diamond and Gold Partners

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

SPERRY SAILS

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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