Sideways, a 2004 Academy Award-winning and Golden Globe Award-winning comedy/drama film, was co-written and directed by Alexander Payne and based on Rex Pickett’s 2004 novel of the same name.

The movie follows the journey of two college friends – Miles, an oenophile and a failed novelist, and Jack, an actor whose heyday is in the past.

“The comically mismatched pair, who share little more than their history and a heady blend of failed potential and fading youth, soon find themselves drowning in wine and women,” according to the official movie description. “Emerging from a haze of pinot noir, wistful yearnings and trepidation about the future, the two inevitably collide with reality.”

Sideways was filmed in the Santa Ynez Valley, located in California's Central Coast. The movie, a surprise hit, helped increase tourism in the area.

For avid fans of the film, retracing the locations used in the filming is simple and many of the landmarks, such as the Hitching Post, Los Olivos Cafe & Wine Merchant and “The Windmill Inn” are well worth the visit.

Los Olivos Cafe & Wine Merchant is where Miles, Jack, Stephanie and Maya went to dinner.
Jack: Did you drink and dial?

Jack: If they want to drink Merlot, we're drinking Merlot.
Miles: No, if anyone orders Merlot, I'm leaving. I am NOT drinking any [expletive] Merlot!