When we moved out of our rental house in September, the plan was to drive up to the Portland, Oregon area for a couple of months before returning to California for Thanksgiving. And rather than simply get in the (fully loaded) car and drive to Portland, we decided to take a few weeks, stopping several places along the way.

Our first stop was in Buellton, California, for three days visiting some of the places from Sideways. (Let me pause here for a moment and suggest that if you have not seen the movie, you should watch it immediately. It’s wonderful. You can finish reading my post after the movie – and it will make a lot more sense.)

We decided to start our wine tasting at Kalyra, the winery where Jack first meets Stephanie. Unfortunately, the winery itself had to close earlier this year due to a lease issue, but they do have a new tasting room in Buellton. So that’s where we went. We tasted some good wines there and at the tasting room right next door. And since it was a Monday, we basically had both places to ourselves, which was great. We got great tips for the next few days, and had a lovely time learning about both wineries.

The next day, at the suggestion of the tasting room manager at Kalyra, we had made a reservation at Beckmen Vineyards, a small, out-of-the-way winery. It was beautiful, the tasting room manager was amazing, and because it was the very first day of the harvest, we got to try some Viognier grape juice right out of the press. And then we went into the barrel room, where she pulled some wine right out of the barrel for us to taste two years before it gets released to the public. This was the perfect way to do a wine tasting. It would be hard to beat.

Our next stop was the Los Olivos Wine Merchant Cafe for lunch, another place featured in the movie. This is the restaurant where Miles, Jack, Stephanie, and Maya had dinner and Miles had his “drink and dial” moment. The food was great, and it was fun seeing where the filmed the scene.

Later, we stopped at Ostrich Land, which appears in two contexts in the movie. They show a short clip from it early in the film, and then after Jack’s rough night with the waitress near the end, he describes having to run naked through an Ostrich farm to get back to the motel. It’s a fun stop, and worth 15 minutes of your time, but there is an admission cost. And let me tell you, up close, those birds are BIG! For a dollar or two, you can feed them.

The next day, it was time to cross off two more key elements of Sideways: Andrew Murray Vineyards and The Hitching Post restaurant. Andrew Murray is stunningly beautiful, and we tasted some great wines, including a very nice Syrah like the one Miles and Maya enjoy at Stephanie’s house. It’s featured in the scene where Maya makes her great seduction speech about wine, and Miles freaks out and runs off to the bathroom to splash water on his face.

Then, for our last night, we wanted to recreate one of the iconic scenes: walking from the Sideways Inn to The Hitching Post. I had always assumed this was filmed elsewhere, and that they did not actually walk along the highway all the way to the restaurant. But it turns out it’s less than a mile, and the car dealerships you see repeatedly in the film (they make this walk multiple times) were right there where we expected them to be.

To top it all off, we had been told on our first day at Kalyra that Wednesday was burger night at The Hitching Post: the one day the sell burgers, made from the trimmings of all the high quality steaks. It was highly recommended, and as more of a burger guy than a steak guy, I thought it was fabulous. If you happen to be there on a Wednesday, I highly recommend it. And it went great with the Highliner Pinot Noir I ordered, a wine that features prominently in the film. And I’m pretty sure we sat the the same table Miles and Jack sat at (or at least a table in the same location given the angle between the table and the grill).

Finally, we got to see the bar where they filmed several scenes, So another fun coincidence that we only realized later when we watched the movie again. And then we had the walk back to the motel. It was a really fun night.

The next morning, we packed up the car and headed off to Yosemite, one my favorite places in the world, but that’s a story for another post.

So, would I recommend this type of “Sideways” trip, and would we do it again? Yes, and yes. Now, understand that I was already a big fan of Sideways, and my wife and I enjoy wine tasting. If you don’t like the movie and don’t like wine, this may not be the getaway for you.

But we had a great time, and I loved seeing so many of the locations from the film, and tasting some of the featured wines. It actually inspired me to create a Sideways viewing party for some friends, featuring carefully curated wine tastings from the movie. But I’ll probably write about that in a separate post.