The Sideways GPS Wine Trail Driving Tour

California’s Santa Ynez Valley has long been known for scenery, but the 2004 film Sideways turned it into a destination for wine fans. This self-guided driving tour follows the region’s microclimates and distinctive wine trails while stopping at recognizable movie locations. It begins near the Santa Ynez River by the bridge at River Course at Alisal, tied to the film’s golf ball battle. Along the route, travelers pass Mission Santa Ynez and the Chumash Reservation, explore Los Olivos, and visit vineyards including Fess Parker, shown in the movie as “Frass Canyon,” where Miles is seen downing the spit bucket. The tour continues to the Sideways Inn (formerly Days Inn) and Hitching Post II, before ending at Ostrich Land. The 90-minute plan also highlights the “Sideways Effect,” multiple wine trails, and mentions sustainable and biodynamic practices.