In 1927, after seven years of Prohibition, Vincent Rizzo had an idea. He would buy a winery. While this may have been an unconventional move, he knew he could get Bernardo Winery at a lower price and keep the business thriving with an unlikely product: olive oil. In a stroke of cunning and arguable genius, the first-generation Rizzo owner made use of the olive trees growing on his property, selling the cold-pressed virgin oil to many of the tuna canneries in downtown San Diego. He also continued production of sacramental wine for the Catholic church and grape juice that was, according to the winery's website, "guaranteed to ferment by the end of the road."

The winery grew to be one of San Diego County's major wine suppliers in the late 1940s, and Vincent turned the family business over to his son, Ross, in 1962. Ross's passion and dedication fueled the winery's success until his passing in 2008. Ross Rizzo, Jr., along with his family now keeps his father and grandfather's legacies alive, adding new varietals and winemaking techniques to the company's repertoire while paying homage to the old ways. Ross still sources his grapes from local vineyards and produces and cellars his wine to develop each variety’s distinct flavor.

Guests can get a behind-the-scenes look at the historic winery during tours and tastings, and the scenic spot also hosts public events and private parties at several outdoor venues and in the Barrel Room, where wooden rafters and huge redwood wine-storage vats create a rustic feel. Once they are done tasting, visitors can wander through a micro village of shops and studios or get a bite to eat at Cafe Merlot. The sprawling property features nods to its storied past with accents such as wagon wheels and an antique thresher machine and events such as grape stompings, otherwise known as do-it-yourself purple pedicures.