Today I want to bring you my guide to a Sideways wine tour in California. The fame of the classic movie that popularized Santa Barbara County wine country is enduring. It gives locals and visitors alike a great excuse to go wine tasting and visit the Sideways movie locations in the Santa Ynez Valley. I’m here now and I can’t wait to show you how to follow in the footsteps of Miles and Jack. I’ve included a map, too.
Sideways Wine Tour
Santa Barbara County is one of my favorite places to go wine tasting in California. Given I go on road trips from San Francisco to Los Angeles a lot, I’m here often. From quick stops to long weekends, my visits have allowed me to discover the area’s highlights and explore a lot of the filming locations from Sideways.
If you’re not familiar with the movie, it’s about two friends (played by Paul Giamatti and Thomas Haden Church) who go to the Santa Ynez Valley for a week-long bachelor trip before one of their weddings. From wineries to restaurants, hotels, and towns, it shows a lot of the best places to visit in the Santa Ynez Valley.
I’ve made it my goal to go to as many of the locations as I can in 24 hours, and now I want to share my itinerary with you so you can do the same. If you’d prefer to go on a guided tour, there are lots of options. You can take a look and book your favorite here.
Los Olivos
I arrive in the Santa Ynez Valley in the late morning, and I start my Sideways wine tour in Los Olivos. This pretty place is home to a long street lined with wine tasting rooms, stylish boutiques, and restaurants. It’s one of the main towns in the area, and it’s a must on any trip to this part of California.
That includes the road trip Miles and Jack take in the movie. They come here to have dinner at Los Olivos Wine Merchant & Cafe. It’s a beloved local restaurant and shop with a wall of wine on one side of the dining room. The famous scene in which Miles over-imbibes and disparages Merlot takes place here.
After doing a bit of shopping on Grand Avenue, I settle in for lunch at one of the outdoor tables at Los Olivos Wine Merchant & Cafe. The food is delicious, and the service is friendly and attentive. Afterwards I pop inside to see where the movie was filmed. The wine wall is still here, and I can see just where Miles, Jack, and their dates sit in the scene.
Wine Tasting in the Santa Ynez Valley
After lunch I head to the next stop on my Sideways wine tour: Foxen. This well-known local winery has two tasting rooms on Foxen Canyon Road in the Santa Ynez Valley.
Miles and Jack belly up to the bar at the foxen 7200 Tasting Room (aka the “Shack”) in the movie. They help themselves to full glasses of wine when their host isn’t looking. The footage appears in a split-screen montage with lots of clips of the region’s vineyards and tasting rooms.
The “Shack” is an open-sided wooden room with a sunny terrace outside. A delightfully rustic place, it features wine barrels as tables. Colorful umbrellas provide shelter from the sun, and there are views of the hills all around.
I settle in at one of the tables to taste a range of Foxen’s Bordeaux and Italian varieties. From Merlot blends to Cabernet Sauvignon, they go down a treat as I channel my inner oenophile a la Miles (Jack doesn’t know much about wine!).
Solvang
The next stop on my Sideways trip itinerary is Solvang. This quirky town is a little slice of Americanized Denmark in the heart of Southern California. Everywhere I look, Scandinavian architecture and Danish flags abound. Then there are the bakeries, souvenir shops, and windmills. I even spot horse-drawn trolleys making their way down the streets.
Several scenes from the movie were filmed in and around Solvang, and my Sideways wine tour hits the best. One of them is Solvang Restaurant. Miles and Jack have breakfast here in a booth with a swan painting overhead. While eating, Jack insists Miles doesn’t let his negative attitude interfere with Jack’s attempts to have a fling before his wedding.
Hitching Post II
Another restaurant that featured heavily in Sideways is the Hitching Post II in nearby Buellton. Miles reconnects with a waitress named Maya while he and Jack are having dinner here. Jack encourages him to pursue her romantically, which he eventually does. Later in the movie Miles returns alone to drink at the bar.
The steakhouse has been popular with visitors following in their footsteps ever since. I’m one of them. 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.
I also make sure to order Highliner, the wine Miles and Jack drink at the Hitching Post II in the movie. It’s a Pinot Noir worthy of a wine snob like Miles, and it goes down a treat in the rustic dining room.
Sideways Hotel
On the way back to Solvang, I pass by the Sideways Inn. It’s the hotel where Miles and Jack stay in the movie (it was renamed after the film came out). A roadside accommodation in Buellton, it features an eye-catching wooden windmill marking the entrance.
Solvang
On my return to the Danish town, I head to my own accommodation, Corque Hotel in Solvang. This boutique hotel features Scandinavian design on the outside and Central Coast chic design on the inside. There’s also a swimming pool and a hot tub for guests to enjoy.
After a good night’s sleep, I head to Solvang Restaurant for one last Sideways experience in the Santa Ynez Valley. I’m lucky enough to be seated at the very same table where Jack and Miles had breakfast in the movie. It’s a great way to end my time in Santa Barbara County wine country.
Sideways Wine Tour
It’s been fun to do a Sideways wine tour, and I’m glad I made the effort to retrace the characters’ steps. While it definitely hasn’t been as wild as Miles and Jack’s road trip, it’s been every bit as enjoyable.
I’ve saved more places from the movie for my next visit, too. From wineries like Firestone and Kalyra to local attractions like OstrichLand USA and Gaviota State Park, there’s plenty of ground to cover.
Sideways Wine Tour Map
As promised, I created an interactive Google map of all the places I visited on my Sideways wine tour. You can see it here. I hope it helps you plan your own fun road trip based on the movie. If you want more, you can see a map with additional filming locations here.
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