The Sideways Trilogy

Sideways is the story of two friends, Miles and Jack, going away together for the last time to steep themselves in everything that makes it good to be young and single: pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country.

It’s seven years after the events of Sideways. Miles has written a novel that has been made into a wildly successful movie, and the movie has changed his life. Jack, contrarily, is divorced, has a kid, and is on the skids. Phyllis, Miles’ mom, has suffered a stroke that’s left her wheelchair-bound and wasting away in assisted living. She desperately wants to live with her sister in Wisconsin. When Miles gets invited to be master of ceremonies at the International Pinot Festival in Oregon, he hatches a harebrained road trip.

Seven years have passed since Miles and Jack took their infamous bachelor trip to the Santa Ynez Valley. Miles has written a novel that was made into a wildly successful movie, which changed his life. Jack, contrarily, is divorced, has a kid, and is on the skids. Phyllis, Miles’s mom, suffered a stroke that left her wheelchair-bound and wasting away in assisted living, and she desperately wants to live with her sister in Wisconsin.

Sideways: Chile follows the further adventures of Miles Raymond (played by Paul Giamatti in the critically acclaimed movie Sideways). It’s now a few years later and Miles is a successful author with a blockbuster movie adaptation under his belt, but he’s still searching for something, and depression has him, once again, in its taloned grip. When he is offered a chance to travel to the country of Chile and visit their wine regions for a magazine assignment, Miles—his world turned upside down by bad financial investments and even worse luck with relationships—happily agrees.

Miles, the now iconic alter ego of author Rex Pickett—who was first introduced in the critically acclaimed book Sideways and its award-winning movie adaptation—resurfaces on the South Island of New Zealand. All he has in life is a half hectare of Pinot Noir, a guest cottage where his days are numbered, a special needs cat named Max, and a winemaker partner pressing him for a more committed relationship.