In 1988, after several years searching either for a suitable vineyard, or for land upon which to plant vines, Tony and Susie Parkinson acquired a 32ha (80 acre) piece of land on the foothills east of McLaren Vale. The property was named Penny's Hill Vineyard, after the hill at the foot of which it sits. The establishment of infrastructure such as bores for irrigation, and the building of sheds and an all-new house, occurred hand in hand with sheep gently grazing, until vines were first planted in 1991.

An initial layout of 2ha (5 acres) with narrower than usual row widths set in place the Penny's Hill viticultural model which between 1991 and 1996 was expanded to 18.4ha (45.5 acres). An additional vineyard of 15ha (37 acres) named Malpas Road Vineyard near Willunga, was purchased in 1993. In 1996, on land adjacent Malpas Road, the Goss Corner Vineyard was established on 10.5ha (26 acres) bringing the total vineyard area to 44ha (108.5 acres).

As quality Shiraz fruit emerged from the new vineyard, Tony Parkinson set about establishing the brand with distinctive 'red dot' packaging and the slogan, 'Proudly Australian. More so McLaren Vale'. During 1997, Penny's Hill 1995 Vintage Shiraz first appeared in the market. Derived from the strong visual presence of 'sold' stickers applied to works in commercial galleries, the 'red dot' is now very much established, not only as the brand's trademark but as a means of visually linking all aspects of the business.

Since the outset, Penny's Hill Vineyards have been tended by viticulturists, David Paxton and Toby Bekkers, with all wines the work of Ben Riggs, a prominent and passionate McLaren Vale winemaker.