Executive V.P. Sheila Stevens is focused on one main thing in life. Running her Minneapolis based advertising agency, and keeping it successful.
When Sheila’s widowed mother suggested they take a well-deserved vacation together to meet new people, she thinks her mom is crazy. When she finds out Marilyn booked them on a motorcoach vacation trip to the Black Hills of South Dakota, she’s convinced her mom is crazy, and it’ll be a disaster.
With a cast of outrageous characters, that include an over the top chain-smoking wisecracker, and two beer-boozer buddies that’ll do anything to stay away from their slot machine addicted wives, Sheila discovers the trip will at least be entertaining.
It soon turns surprisingly interesting, when she meets the attractive J.T. Williams, who’s not the typical motorcoach driver you’d normally see. J.T. and his sister Shelly work as tour guides for their parent's business, and will be taking over for them while they’re out of town on vacation. J.T. gets the opportunity to drive the motorcoach to his favorite destination, the Black Hills – where his family owns a vacation cabin near the historic town of Deadwood.
J.T. does his best as Sheila’s personal tour guide, and takes her on a few adventures she’s never experienced before, and shows her how great life can be outside of the office. While Sheila in turn, finds out about the amazing personality and musical talent J.T. possesses, and she tries to help him realize the unlimited potential she sees in him.
With the help of the beautiful Black Hills, and a group of newly formed friends, Sheila’s disastrous vacation soon turns into an adventure she’ll never forget.