Sideways movie cover Movie Locations Guide

Where was Sideways filmed?

2004

About Sideways

In this Oscar-winning adaptation of Rex Pickett’s novel, we meet Miles (Paul Giamatti) and Jack (Thomas Haden Church), as they have one last road trip in Wine Country before Jack gets married.

Miles is a failing author and considers himself a wine expert. Along this journey, he aims to teach his friend Jack the finer points of wine tasting, when really, all Jack wants to do is drink wine and have fun. The weekend plan is simple, drink great wine, play some golf and eat some amazing food before Jack gets hitched.

Along the way, the pair meet waitress Maya (Virginia Madsen) and tasting room worker, Stephanie (Sandra Oh), who they end up spending more and more time with. As the wedding gets ever closer, things get more complicated than either of them meant it to.

At its heart, Sideways is a film about friendship, having fun, and helping each other get through tricky periods. The amount that you learn about different wine varieties throughout the film is pretty cool too! The all-star cast manages to split between comedic and heartfelt moments that really allow you to empathize with the characters – even when they do something awful, which in this film, is pretty often!

Having had its debut on the film festival circuit at the Toronto International Film Festival (TIFF), Sideways garnered both critical acclaim and a loyal bank of fans along the way. Despite the now A-list cast, when you watch this film it feels like a low-budget indie in the absolute best way. It feels like you’re truly joining two friends on a road trip, and watching them make mistake after mistake.

If you love wine, California, road trips, or just any film about what it is to be human, Sideways is a great film for you to spend a couple of hours watching.

City Locations

Solvang, California

Location Types

Ranch, America, NatureScapes

Location Styles

Anywhere America/Americana, Ranch, House

Sideways Locations

Sideways Locations

In order to create a movie that revolves around tasting wine, you need to go to wine country. Instead of heading north to Napa, the Sideways production team opted to stay true to the locations in the original Rex Pickett novel and shoot around the Solvang area.

Located in the Santa Ynez Valley in Santa Barbara County, Solvang and the surrounding wine-heavy towns are popular with groups of friends looking to have a boozy getaway, or those looking for vineyard-based weddings. This makes it the perfect spot for this particular film, both as a setting, but also because there are so many vineyards for film shoots within a relatively small area.

Essentially, if you wanted to recreate Miles and Jack’s road trip up from Los Angeles, it’s completely doable. Simply head north on the 101 Pacific Highway until it becomes Highway One and you’re there. From here, you can stop by pretty much any town in the area and the likelihood of there being a vineyard is really high. It’s that good for winemaking.

Just make sure you have a designated driver on hand, or a hotel booked ahead of time. It’s a popular area, so there are plenty of wine tasting tours and taxi companies in this region, specifically for wine tourism. You’re in good hands!

Miles teaches Jack to taste wine scene in Sideways

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.

The golf scene in Sideways

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?

Stephanie finds out about the wedding scene in Sideways

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.

Everyone meets for dinner scene in Sideways

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.

Miles drinks the swill bucket scene in Sideways

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.

The guys meet Stephanie scene in Sideways

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.

Conclusion

All in all, Sideways is a deeply entertaining film and is a must-visit for anybody who loves indie filmmaking and wine. With hilarious and heartfelt performances from Giamatti, Haden-Church, Oh, and Madsen, it’s a film that you can definitely watch again and again.

The fact that the filming locations in Sideways are actually in the small winemaking towns that they name in the film is also a nice touch. When you’re walking around Solvang, Buellton, or Los Olivos, it feels like you’re actually on the set of Sideways, which is super cool.

With the different Sideways filming locations being so close to each other, it’s actually really easy to plan a trip to visit all the different destinations used in the movie. So, brush up on your wine tasting technique, grab your golf clubs and head out to the Santa Ynez Valley for a long weekend of delicious wine tasting. Broken noses and public breakdowns are entirely optional.