Sideways in Santa Barbara

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.

Sideways-winecountry-roadtripDirected 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 and 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.


Miles & Jack wine tasting at Sanford Winery.
Miles & Jack at Sanford Winery. Photo Credit: Twentieth Century Fox Film Corporation

Start your “Sideways” tour with breakfast at Solvang RestaurantAs 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.


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.


sideways_picnic-600Wine tasting awaits as your “Sideways Tour continues into the afternoon at Fess Parker Winery & Vineyard. See where Miles phones his agent and finds out his book will not be published.  After the pourer refuses to serve him a full glass, Miles guzzles the spit bucket. Instead of the spit bucket, we’d opt for a glass of Fess Parker Pinot Noir.

Set your glass aside for a winery tour at Firestone Winery. Tours are offered three times a day and guide visitors through the history of the winery and the production process from vine to glass. This winery made its mark in “Sideways where Miles, Jack, Maya and Stephanie sneak out of a wine lecture to share a romantic walk through the Barrel Room.

After a day of tasting, finish up your “Sideways Tour with a traditional “Santa Maria Style BBQ” dinner at the Hitching Post IIMiles and Jack share a bottle of Highliner at the bar. While having dinner, they talk to Maya who waits tables. Later, Miles returns on his own.

For those looking to extend their time in wine-country, we’ve listed more Santa Barbara County locations highlighted in the movie:

 AJ Spurs: Miles and Jack meet a waitress named Cami who Jack gets tangled up with later that night.

Andrew Murray Vineyards: Miles and Jack drive through the wine country.

Foxen Winery: During the split screen portion of the film, Miles and Jack each help themselves to a full glass when the pourer turns her back.

Lompoc Farmers’ Market (Friday’s, 2-6 p.m.): Miles and Maya walk through the market.

River Course at the Alisal Guest Ranch: While golfing, Miles and Jack frighten the impatient foursome chipping into them.