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A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanies friend Maya but when he lets slip that Jack is about to be married any hope of a relationship seems to be lost.
Miles Raymond is a hopeful but struggling writer who also happens to be a wine connoisseur. Jack Cole is a fading actor and his soon-to-be married friend. To celebrate Jacks concluding days as a bachelor, they will embark on a wine-tasting road trip through Californias renowned vineyards. As they travel through the countryside, the two men confront their trepidation about what their futures hold and contemplate the paths in which they want to follow.
Paul Giamatti
Miles
Thomas Haden Church
Jack
Virginia Madsen
Maya
Sandra Oh
Stephanie
Marylouise Burke
Miles's Mother
Jessica Hecht
Victoria
Missy Doty
Cammi
M.C. Gainey
Cammi's Husband
Alysia Reiner
Christine Erganian
Shake Tukhmanyan
Mrs. Erganian
Shaun Duke
Mike Erganian
Robert Covarrubias
Miles's Building Manager
Patrick Gallagher
Gary the Bartender
Stephanie Faracy
Stephanie's Mother
Joe Marinelli
Frass Canyon Pourer
Chris Burroughs
Chris at Stanford
Toni Howard
Evelyn Berman-Silverman
Khoren Babouchian
Armenian Priest
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