With the 1990s came another generation of Kingstons and new possibilities for The Farm. While in graduate school at Stanford University, Courtney Kingston wrote a business plan that had little to do with cattle and traditional farming: She wanted to plant a vineyard in the far western hills of Casablanca.

Planting their first grapevines in 1998, the Kingstons bet on pinot noir and syrah in a valley known exclusively for white wines. Inspired by California vineyard leaders like David Hirsch and Gary Pisoni, they planted a vineyard up in the hills and gambled on the future of cool climate reds. In 2003, they made 400 cases of pinot noir and syrah under their own Kingston Family label to showcase the potential of coastal Chile for world-class wines.