It has been 10 years since the movie Sideways came out. That makes me feel two things: 1) really old, and 2) embarrassed that I have never retraced the steps of Miles and Jack’s wine tasting adventures in California. But now that I’m in Santa Barbara with Visit California, I have the perfect excuse to head over to the Santa Ynez Valley to follow in the footsteps of Sideways.

Wine Tasting Room in Los Olivos, California

I start out in Los Olivos, a small rural town with a main street lined with wine tasting rooms and restaurants. One of them is Los Olivos Wine Merchant Cafe, a restaurant with a pretty wall of wine where the famous scene in which Miles disparages Merlot was filmed. I have lunch there with the owner, who shares stories about the filming while a live guitarist plays in the background.

Los Olivos Wine Merchant Cafe in California

From there I stop at Foxen Wines, a tasting room on Foxen Canyon Road. Here Miles and Jack bellied up to the bar for a tipple, and I do the same. The ambiance is rustic, with the space consisting of an open-sided wooden room and a sunny terrace in the back.

Foxen Wines in the Santa Ynez Valley, California

A bit farther south, I arrive in surreal Solvang, a kitsch slice of Denmark in the heart of Southern California. Everywhere I look, Scandinavian architecture and Danish flags abound, and in the heart of it all is the Solvang Restaurant. Miles and Jack had breakfast here in a booth with a swan painting overhead, and I am lucky enough to be seated in the very same spot.

Solvang Restaurant from Sideways in California

Another restaurant that featured heavily in Sideways is the Hitching Post II in nearby Buellton. Miles met Maya there in the movie, and the steakhouse has been popular with visitors following in their footsteps ever since. I settle in for dinner, sneaking glances at the bar every once in awhile just to make sure I don’t miss a repeat performance.

The Hitching Post in Solvang, California

On the way back to Solvang, I pass by the hotel where Miles and Jack stayed, a roadside inn with a large wooden windmill marking the entrance.

Solvang, California

And then it’s time to head back to my own hotel to pack my bags and travel to London. My five weeks in California have been amazing, and wrapping them up with a Sideways wine tasting trip in the Santa Ynez Valley has been a great final adventure. And while it definitely hasn’t been as wild as Miles and Jack’s road trip, it has been every bit as exciting.

12 Comments on Lady on the Sideways Wine Trail

  1. How fun! I haven’t thought about that delightful moving in ages. I’ve been to two wineries near Santa Barbara, but there were out in rolling green hills and we enjoyed a picnic lunch. Next time I’d like to try this route!

  2. I’ve been working on a Sideways location map…more detailed than the ones you can currently find. I would have liked to have shared it with you before you started your trip, but I just found this site.

    Awesome that people are still visiting the Sideways locations 9+ years (not quite 10… the movie debuted on 9/13/04 in Toronto, limited release in the US starting on 10/12/04, and fully released in the US on 1/21/05) after it was released 🙂

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