Making its debut in 2004, the cult-classic film Sideways made a star out of Santa Barbara wine country and drummed up demand for pinot noir around the world. And if you’ve ever tasted the elegant, “quaffable” pinot noir of Santa Barbara wine country, you already understand why.
Directed by Alexander Payne, the Oscar® winning film for best adapted screenplay, based on the novel by Rex Pickett, tells the story of a celebratory road trip saluting Jack’s (Thomas Haden Church) final days as a bachelor. A sojourn in Santa Barbara County’s verdant wine country quickly turns sideways as he and Miles (Paul Giamatti) hit the gas en route to mid-life crises. The unlikely pair share a heady blend of failed potential, fading youth and a nose for drowning in wine and women (played by Sandra Oh and Virginia Madsen).
While we don’t recommend having the same experience as our friends Miles & Jack, you too can taste your way through Santa Barbara wine country on the same path forged by the unlikely duo. To make sure your day doesn’t go sideways, we’ve crafted an itinerary including iconic film locations from the movie.
If you’d prefer to route your own path, click here to download the Sideways Map.
Morning

Start your Sideways tour with breakfast at Solvang Restaurant. As they sit down for breakfast, Jack grumpily insists that Miles’ gloominess not thwart his attempts to get lucky before the wedding. Once your bellies are filled with Aebleskiver (a waffle-like breakfast ball filled with apple slices), wine tasting awaits at Sanford Winery, where Miles teaches Jack the basics of wine tasting. Chris Burroughs starts them off with the Vin Gris in which Miles smells citrus, strawberry, the faintest soupcon of asparagus and just a flutter of a nutty edam cheese.
Following Sanford Winery, continue tasting at the next location, Kalyra Winery, where Australia meets Santa Barbara County. Here, Miles and Jack meet Stephanie, a flirtatious wine pourer who becomes the object of Jack’s affection.
Mid-day
You are truly in for a once-in-a-lifetime experience with a stop at Ostrich Land. If you have never been up close to an ostrich or have not had the opportunity to feed one, this is a “must-do” along The Sideways Trail. Rare and unique for this part of the world, visitors can’t help but smile and leave amazed. Ostriches seen while Miles, Jack, Maya and Stephanie drive to the picnic. Later, Jack gets acquainted with them on his “run” from Buellton to Solvang. After feeding ostrich, continue in the footsteps of Sideways to Los Olivos Café & Wine Merchant. Los Olivos Café is where Miles, Jack, Maya and Stephanie enjoy dinner and several exquisite bottles of wine. If you have the patience to wait for dinner, there’s even a Sideways menu to order from. Just note, it’s for dinner only.