[4] The series spans approximately eight years in the life of its main protagonist, a writer named Miles.
At the beginning of Sideways, Miles is a mostly unsuccessful screenwriter and functioning alcoholic who is taking his best friend Jack, a successful TV director, on a trip to California's wine country the week before the latter's wedding.
Vertical takes place seven years later, during which time Miles has found literary success with the publication of a novel based on the adventures he and Jack experienced in the trilogy's preceding installment.
Jack, on the other hand, has seen his fortunes decline following a divorce and an increasing alcohol problem.
[5] A play adapted by author Rex Pickett from the Sideways novel was produced at multiple theaters in the United States and the United Kingdom, including at the La Jolla Playhouse.