San Francisco to Calistoga via the Silverado Trail: about 105 miles
Why go: California's—and the country's—very best wines come out of Napa, thanks to a perfect climate-and-soil combination for growing Cabernet Sauvignon. Among Napa's stellar wineries: Jarvis Winery, Joseph Phelps Vineyards, and Kuleto Estate (all require reservations). Those who want to make their own wines can attend a blending session at CrushPad.
Where to stay: Solage Calistoga features stand-alone studios with private patios (Double from $325 to $395).
What to eat along the way: Gott's Roadside in St. Helena is beloved for its Niman Ranch burgers and crispy ahi poke tacos; Thomas Keller serves an unparalleled family-style menu at Ad Hoc in Yountville.