We’ve all been there… Middle-aged, past your prime, trying to navigate the restless sense of ennui that plagues the privileged and self-centered. Well, that’s nothing a little wine-tasting, casual sex and a good road trip can’t fix! So, pop open a bottle of your best Cabernet (NO MERLOT!) and enjoy a Sideways road trip through the Santa Barbara filming locations.
Most of the filming was done north of L.A., between San Louis Obispo and Santa Barbara. As you head out of Los Angeles you’ll pass the iconic round, boutique hotel, the Hotel Angeleno (as seen at the beginning of Sideways and where Al Pacino moves into the movie Heat).
The first winery Miles (Paul Giamatti) and Jack (Thomas Haden Church) hit up is Sanford Winery in Lomboc, CA. Here Miles attempts to teach a gum-chewing Jack about the fine art of wine tasting.
The guys then travel to Solvang, CA. This is an amazing town that was built back in 1911 by “adventurous Danish-Americans” who purchased 9,000 acres to create an authentic northern European village. The entire town is comprised of 15 inns, a guest ranch, over 30 restaurants, 150 boutique stores and and an outdoor 700-seat theater.
They then walk to the Hitching Post II, where they meet Maya (Virginia Madsen).
The two then have a tense breakfast at the Solvang Restaurant.
The next stop on our wine-fueled adventure takes Miles and Jack to the rustic tasting room at Foxen Winery (according to them, the author of the book Sideways based Mia on the then-tasting room manager at Foxen, Sandy).
From there, they head back down to Santa Maria to Kalyra Winery, where they meet up with sassy Stephanie (Sandra Oh).
The four then enjoy a lovely dinner at Los Olivos Cafe, where Miles infamously declares: “I am not drinking any fucking Merlot!” The Cafe's wine wall makes it a perfect place to take a date to chat about wine, and enjoy a delicious meal and a massive selection of incredible California vinos.
Awkwardly-sweet romance ensues, which involves bowling at Ocean Lanes (now closed) and golf at River Course (Alisal Guest Ranch).
Meanwhile, Jack, Miles and Maya escape a boring lecture at Firestone Winery by hiding out in the barrel room, followed by a romantic stroll through the Lompoc Farmer’s Market.
Fess Parker Winery is where Miles discovers that his novel won’t be published and then attempts to drink the spit-bucket, cause that’s totally an appropriate response. Gross!
Jack gets even more naughty with a married waitress who works at AJ Spurs in Buellton.
Miles finally opens his 1961 Cheval Blanc at Orcutt Burgers in Santa Maria (it’s supposed to be San Diego in the film). It’s not all bad though, because Orcutt is considered the best burger places in the region.
