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A wine lover’s weekend spent ‘Sideways’ in the Santa Ynez Valley

Twenty years after the Oscar-winning film's debut turned Santa Ynez Valley from one of the country's best-kept secrets for wine enthusiasts into a top destination for wine travel, the area remains a rather quaint place to visit. Indulge in world-class wine and lively local fare with our tour of Miles Raymond's favourite haunts.

Twenty years on, ‘the Sideways effect’ continues in the Santa Ynez Valley. The film, directed by Alexander Payne, follows the misadventures of two middle-aged friends on a bachelor weekend road trip through Santa Barbara’s Sta Rita Hills, visiting some of the area’s most celebrated vineyards and restaurant staples.

The protagonist, Miles, played by Paul Giamatti, is a struggling writer and amateur wine enthusiast. An ardent supporter of the cool climate Pinot Noir produced in the Sta Rita Hills, he takes his best friend, washed-up actor Jack Cole, to experience the region’s wines just before Jack’s wedding.

Along the way, Miles notoriously professes an ironic hatred for Merlot while putting Santa Barbara Pinot Noir on a pedestal, only to later drink the wine he’s been saving for the right moment, a 1961 Château Cheval Blanc from a paper cup. The special wine is, of course, a Merlot blend.

Miles’s declaration seems to have famously influenced wine market trends for drinkers everywhere. A closer look at the film reveals a few subtly embedded wines that are worth seeking out on a Santa Ynez Valley tasting tour.

Santa Barbara locals agree that despite their often cringeworthy behaviour, the humorous duo gives a genuine look into a wine region still not overexposed by corporate marketing teams or Instagram influencers while yet honouring its innate authenticity.

Like Santa Barbara’s local Pinot Noir, the Sideways film aged beautifully, and its wine trail remains a wonderful choice for a weekend visit.

At the Hitching Post II, Frank Ostini serves Santa Maria-style BBQ steaks. Credit: Jeremy Ball



There are hundreds of accommodation options to choose from in the Santa Ynez Valley, but the Sideways Inn from the movie will please film buffs and wine enthusiasts alike. Start your Sideways weekend by checking into the hotel in Buellton.

While certainly not the most luxurious option in the area, the inn remains affordable and wonderfully nostalgic for fans of the movie. Travellers need not worry; the inn has been completely renovated since the film, and it’s perfectly comfortable for a night (or two) after tasting in the area.

*Be sure to take advantage of the included breakfast delivery programme. Order by 6pm to receive the next morning.

Fans of the film and those looking for a local bottle selection to pair with dinner will appreciate the Sideways Inn’s proximity to the Hitching Post II restaurant, situated just off the highway and about a 15-minute walk from the inn.

In addition to claiming the ‘world’s best BBQ steaks’, this casual dining room has remained almost unchanged since the film’s debut. Despite the dated interior, you can expect to find Santa Maria-style BBQ grilled to perfection over an open fire and, of course, delicious Pinot Noir.

The restaurant’s owner, chef and winemaker, Frank Ostini, grew up in the wine business and has been both cooking and making wines in Santa Barbara County since 1979.

Look out for bottlings from his favourite vineyards – Sanford & Benedict and Fiddlestix – blended into the Hitching Post’s ‘Perfect Set’ cuvée. Ostini notes: ‘We like ’em at least five years old, but all our wines are balanced. It’s really all about balance for ageworthy wines.’ Notable vintages to try are the 2016 and 2017.

Foxen Canyon Road, a narrow country road, runs through the heart of Santa Barbara County wine country. Credit: George Rose / Getty Images News



Take breakfast at the hotel, or stop at a local coffee shop before heading out to enjoy a morning of winery visits on Foxen Canyon Road.

Located in the heart of the Sta Rita Hills, this picturesque stretch provided the backdrop for most of the film’s iconic vineyard scenes. Be sure to pace yourself, or better yet, book a driver to fully experience the region’s bounty.

First stop; Firestone Vineyard tasting room, where Miles, Maya, Jack and Stephanie take their own private tour of the wine cellar. Firestone Vineyard is known as the first estate winery established in Santa Barbara County in 1972 and is still among the most recognisable spots to visit.

Make an optional stop at Andrew Murray Vineyards to taste the Estate Syrah – drunk during one of Miles and Maya’s most intimate conversations in the film, ironically about Pinot Noir. Don’t miss the Viognier, a local favourite. Or opt for Fess Parker winery, known as ‘Frass Canyon’ in the film, and chosen for Miles’ infamous tantrum scene after receiving a disappointing call from his publisher.

Finally, visit Foxen Wineries 7200 Tasting Room ‘Shack’, where a countertop tasting scene was filmed.

Wineries along Foxen Canyon Road are great for experiencing a traditional seated tasting nestled among a vineyard setting. While walk-ins are still accepted, appointments should be made to secure your booking.


After a busy morning of tasting, stop for lunch in downtown Los Olivos. Nestled among the shops and tasting rooms is Los Olivos Wine Merchant & Cafe, where Maya orders a glass of Fiddlehead Cellars Sauvignon Blanc, aged 12 months in French oak, and shares one of the first vulnerable moments of connection with Miles over a glass of wine that isn’t Pinot Noir. The café has lovely terraced seating and a full retail shop featuring both local and international wines for purchase by the bottle.

After lunch, discover downtown Los Olivos and opt to sample wines from the nearly 30 wine tasting rooms, most of which benefitted from ‘the Sideways effect’, bringing interest to the area.


Try dinner at Bar Le Côte or the aptly named Mattei’s Tavern in Los Olivos. Both restaurants are housed in historic tavern-style buildings predating the vineyards that surround them. Look out for bottlings from Sea Smoke, Fiddlehead, Melville, and Whitcraft, all featured in the movie.

image of Kathy Joseph with actress Virginia Madsen

Santa Barbara County winemaker and icon Kathy Joseph with actress Virginia Madsen during the filming of Sideways. Credit: Fiddlehead Cellars


After a Danish breakfast in neighbouring Solvang, head over to Fiddlehead Cellars’ tasting room for a glass of Honeysuckle Sauvignon Blanc in the ‘Lompoc Wine Ghetto’. This industrial tasting zone, often overlooked by wine country travellers, is well worth a visit to taste wines from several producers. Fiddlehead Cellars was a frequent stop for the cast of Sideways, and the Honeysuckle Sauvignon Blanc was a favourite of director Alexander Payne off-screen. Winemaker Kathy Joseph is known to cellar her wines extensively before release and current vintages of Honeysuckle being poured at the tasting rooms are typically 10-12 years old. All of them are outstanding, but the 2003 from the movie is still available (while supplies last) and remarkably fresh.

Take a scenic 15-minute drive on the locally famous Santa Rosa Road to Sanford Winery & Vineyards. This is where Miles introduced Jack to his first tasting flight where citrus, strawberry and ‘the faintest soupçon of like asparagus and just a flutter of a, like a, nutty Edam cheese’ were all found in a glass of Vin Gris.

Sanford Winery’s previous owner, Richard Sanford, established the first Pinot Noir vines in the area back in the early 1970s. Many winemakers still source their fruit from the original flagship vines at nearby Sanford & Benedict Vineyard.

Another option is Melville Winery for single vineyard Pinot Noir served on picnic tables with options for cheese and charcuterie board pairings. A bottle of Melville Pinot Noir was conveniently placed on Miles’ nightstand throughout the film and presumably consumed during his lonely nights in the Sideways Inn. Both stops give visitors one last glimpse into the heart of Miles through Santa Barbara’s most iconic grape – Pinot Noir.

The vines at Sanford Winery. Credit: Terlato Wine Group

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