Where was Sideways filmed?

At one of the first tasting rooms that the pair visit on their weekend away, Miles attempts to teach Jack how to correctly taste wine. First swirling, then sniffing, and finally tasting, before using the swill bucket.

After allowing Miles to go through the motions, Jack chugs the wine. Miles looks at him afterward and notices something unbelievable.

“Are you chewing gum? Spit it out”. Anybody who’s trying to actually taste a wine will know what a cardinal sin this truly is! Definitely not the best start to the trip for the pair of them!

This particular tasting room can be found at the Sanford Winery, located on 7250 Santa Rosa Road, Buellton, California. Open from 11-4 daily, the Sanford Winery specializes in hand-crafted Pinot Noir.

As with a lot of the vineyards featured in the movie, you are going to have to drive to access them as they’re out in the middle of nowhere. Of course, don’t drink and drive, or try and get on a wine tasting tour.

One of the key tenets of the weekend was to have fun and play some golf. Having, according to Jack, forgotten how to have fun, the pair hit the course.

Jack goads him by saying, “We’re gonna go have some fun, do you remember fun Miles?”

While they’re on the course, things go a little bit sideways – pun fully intended – when Jack keeps asking Miles about his novel. This is a manuscript that still hasn’t been picked up and is a source of much anxiety for Miles. Eventually, Miles snaps, taking all his rage out on the ball in spectacular fashion.

The golf course that is used as a Sideways filming location is the River Course at the Alisal, based at the Alisal Guest Ranch in Solvang, California. In addition to a first-rate golf course, visitors can also stay at the resort and indulge in a premier dining experience.

It’s just under a mile from the main road where the Los Olivos Loop and Express buses stop on Mission Drive, so you can walk, but there is also tons of on-site parking available. Besides, who wants to carry their clubs all that way?

Jack’s philandering habits come back to bite him in this tumultuous scene. Following Miles’ minor breakdown at a vineyard, Jack drives him back to the motel to sober up and recover. When they pull up, the pair are greeted by a very angry Stephanie, who’s just found out from Maya that Jack is engaged.

“You’re getting married on Saturday?!” she yells before slamming her motorcycle helmet into Jack’s face, breaking his nose. Seems an appropriate response to me…

Jack and Miles’ motel is used a couple of times throughout the film and is called the Windmill in the movie. In real life, the filming location was the Days Inn Buellton, which can be found at 114 East Highway 246, Buellton, California. It’s since been renamed the Sideways Inn in honor of the film’s popularity.

As it’s in central Buellton, just off the expressway, there are plenty of bars, restaurants, and shops to explore. You can get the express bus that stops a few streets over, but if you’re staying at the Sideways Inn, you should be able to park there.

After meeting Maya and Stephanie separately, the group reconnects to go for dinner together and drink some more wine. Miles is already reluctant to have a sort of double date with his friend who’s about to get married so is in need of persuading by Jack.

Outside the restaurant, Jack suggests that the women might want to drink merlot – something unthinkable for Miles and his so-called superior taste, leading to this outburst:

“If anyone orders any merlot, I am leaving. I am not drinking any merlot!” To each their own, I guess!

This particular Sideways scene was filmed at Los Olivos Cafe and Wine Merchant, which can be found at 2879 Grand Avenue, Los Olivos, California. Located in the heart of Los Olivos, which is also a massive wine town, there are plenty of wine bars and restaurants on this street alone that visitors and locals alike can enjoy.

Literally round the corner from Los Olivos Cafe and Wine Merchant, you’ll find the bus stop for the Los Olivos Loop, meaning you can drink plenty of delicious wine and still get back to your accommodation without expensive taxis or illegally getting behind the wheel.

There are low points and then there’s being refused service in a tasting room and trying to drink the swill bucket. Miles hits this dizzying low after receiving a call from his agent saying that pretty much everyone was passing on the manuscript of his novel.

This together with the fact that Jack said he loved Stephanie and was going to leave his fiancee and move up here, Miles accidentally telling Maya that Jack was engaged, and Maya subsequently dumping him – it’s safe to say Miles has had better days.

When Miles reaches over the counter to grab a tasting bottle after being cut off, he tells the attendant “I told you, I need a drink so I’m gonna help myself”. Not a good move.

This particular tasting room can be found at the Fess Parker Winery & Vineyard at 6200 Foxen Canyon Road, Los Olivos, California. Located on a road that is littered with wineries and vineyards on either side, heading north out of Los Olivos, it’s a popular stop for wine tours in the area.

Bringing your furry friend? Fess Parker Winery and Vineyard are also dog-friendly! Due to its remote location, you’re either going to need a designated driver or a number for a local taxi company. The guys at the winery should be able to help you with the latter.

When we meet Stephanie, she’s running a wine tasting for Miles and Jack. Miles is distinctly unimpressed with all the wines, while it’s apparent that Jack is just trying to flirt – something that Stephanie is definitely picking up on.

After a few tasting room tours with somewhat stingy pours, Stephanie has a bit more of a heavy hand, to which Jack says, “Now there’s a girl who knows how to pour”.

This decidedly more laidback winery is the Kalyra Winery located at 343 North Refugio Road, Santa Ynez, California. Again, you’ll find the Kalyra Winery on a road heading out of Santa Ynez town that’s dotted with several vineyards and wineries. You could literally have a wine tasting tour on this short road alone.

It’s only a one mile walk from the express bus stop on the main road – Mission drive – if you don’t have a designated driver or you don’t want to pay for a tour or taxi. You’ll actually pass another vineyard on the way to the Kalyra entrance, so if the mile walk feels too long, you can always take a quick break to taste some delicious wines.