Abecassis enrolled Yankee under the burgee of the Corinthian Yacht Club, founded in 1886 to champion amateur, hands-on seamanship. He was shrewd enough to secure the ablest skipper available: Carl Westerfeld, a past flag officer of the Corinthian and one of the most respected racing helmsmen on the Bay.

Yankee made her competitive debut in the Admission Day Regatta of September 1906 — and won. A contemporary account noted the excitement surrounding the new yacht’s first appearance under racing canvas, reporting that Westerfeld sailed a splendid race and that Yankee posted the fastest time on the course, besting the sloop Presto by two minutes and forty-seven seconds. The victory earned her the first of two McDonough Cups, donated by J. M. McDonough, a remarkable act of sporting patronage given that McDonough himself had suffered heavy losses in the fires following the earthquake. The sterling silver trophies from 1906 and 1907 were produced by the San Francisco jeweler Shreve & Company and weighed 44 and 27 ounces respectively. In a remarkable episode a century later, these trophies were recovered from a grandson of Abecassis living in Toulon, France, who had found them in his grandfather’s basement and located the Yankee crew through the internet.

The crowning achievement of the Abecassis ownership came in September 1907, when Yankee won the inaugural San Francisco–to–Farallon Islands ocean race, the first offshore race ever sailed from San Francisco Bay, contested for a trophy donated by San Francisco Yacht Club Commodore Francis G. Phillips. The course ran from the Bay out through the Golden Gate, twenty-seven miles to the barren granite outcrops of the Farallon Islands, and back. With Westerfeld again at the helm, Yankee prevailed over larger and reputedly faster competitors, including her own Stone-yard sistership Martha, some fifteen feet longer and brand new. The Farallones Race would go on to become one of the defining events of Bay sailing, running for over a century. Yankee, at one time, was said to hold the record for the return leg from the islands — having caught a perfect following swell and surfed most of the way back to the Golden Gate.

But Yankee’s first chapter was brief. Mrs. Abecassis, deeply shaken by the 1906 earthquake, became increasingly determined that her family should leave San Francisco. Some accounts suggest she prepared to depart with the children if necessary. David Abecassis eventually yielded, and in 1907 he put Yankee up for sale and moved the family east.