Jack and Miles were college roommates, and despite their differences, they have been friends ever since. Jack is an actor, whose career high point is a stint as a soap opera regular. English teacher and oenophile Miles would much rather be a published novelist. Jack is about to get married, so depressed, divorced Miles suggests they hit the road for a week-long bachelor party amidst the rolling hillsides and gorgeous sunsets of wine country near Santa Barbara. A little golf, a lot of wine, how could it possibly go sideways?