Lady’s Sideways Wine Tour Guide

Today I want to bring you my guide to a Sideways wine tour in California. The movie popularized Southern California wineries in the Santa Ynez Valley, and it’s fun to visit the filming locations here.

Sideways Wine Tour

It’s been over a decade since the movie Sideways came out. This makes me feel two things: 1) really old, and 2) embarrassed that I’ve never retraced the steps of Miles and Jack’s wine tasting adventures in California.

But now that I’m in Santa Barbara as a guest of Visit California, I have the perfect excuse to head over to the Santa Ynez Valley to follow in the footsteps of Sideways.

Los Olivos, California

I start my Sideways wine tour 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 here with the owner, who shares stories about the filming of Sideways while a live guitarist plays in the background.

Foxen Wines

The next stop on my Sideways wine tour is Foxen Wines, a tasting room on Foxen Canyon Road. Miles and Jack bellied up to the bar for a tipple here, 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.

Solvang, 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.

Several scenes from the movie were filmed here, and my Sideways wine tour hits the best.

In the heart of town lies Solvang Restaurant. Miles and Jack had breakfast here in a booth with a swan painting overhead, and I’m lucky enough to be seated in the very same spot.

Hitching Post II

Another restaurant that featured heavily in Sideways is the Hitching Post II in nearby Buellton. Miles met Maya here in the movie, and the steakhouse has been popular with visitors following in their footsteps ever since.

My Sideways wine tour brings me to the Hitching Post II for dinner, and I sneak glances at the bar every once in a while to make sure I don’t miss a repeat performance.

Sideways Hotel

On the way back to Solvang, I pass by the Sideways Inn, the hotel where Miles and Jack stayed. It’s a roadside accommodation with a large wooden windmill marking the entrance.

Sideways Tour

And then it’s time to head back to my own hotel in Solvang to pack my bags and travel to London.

My five weeks in California have been amazing, and wrapping them up with a Sideways wine tour in the Santa Ynez Valley has been a great final adventure.

While it definitely hasn’t been as wild as Miles and Jack’s road trip, it’s been every bit as exciting.

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