The Sideways Wine Country GPS-Guided Driving Tour

The Sideways wine country is positioned as more than scenery in a GPS-guided self-drive tour that ties California’s Santa Ynez Valley to the 2004 film Sideways. The route begins near the Santa Ynez River by the River Course at Alisal, referencing the golf ball battle location from the movie, and then continues through towns and scenic roads past Mission Santa Ynez and the Chumash Reservation. Along the way, visitors can explore Los Olivos and visit vineyards including Fess Parker, identified as “Frass Canyon” in the film, with the tour also citing Miles’ spit-bucket moment. The drive finishes at Ostrich Land and culminates at the Sideways Inn (formerly Days Inn) and the Hitching Post II restaurant, where Maya is a key element in the story. The 90-minute TourFreely experience is smartphone/GPS guided and available 24/7.