It's a few days before Christmas. As they have always done, widowed schoolteacher Tom Pullman, his 13-year-old daughter Hilly, and their dog Toby are driving from their Chicago home to Vail, Colorado to spend Christmas with Tom's mother Rheudel. Hilly loves her grandmother, but she wishes for a more exciting Christmas, and she would rather fly than drive in Tom's aged pickup truck, which may not last this trip. But her father finds taking the back roads and enjoying the countryside to be part of the adventure. Meanwhile, Chicago-based fashion photographer Claire Jamison, a pampered city girl, has one more assignment, after which she will fly to Aspen to join her Italian fiancé Lorenzo at his chalet where they will get married on Christmas Eve. Although they have known each other for some time, the romance, engagement, and wedding are recent phenomena, and Lorenzo is handling the bulk of the wedding plans with the help of his personal assistant Michele. Almost everyone Claire tells about the wedding is skeptical, if only because of the stereotype of Italian men being Latin lovers, meaning that Lorenzo will have a wandering eye that maybe has already wandered. Claire's assignment is canceled at the last minute and she plans to fly to Aspen early to surprise Lorenzo, but soon her flight is diverted to Lincoln with no guarantee that any form of transportation will be available to get her to Aspen on time. As Claire and Hilly have seen each other from afar a few times on this trip, they believe it may be kismet when they cross paths in Ogallala, Nebraska, where she is in total distress and Tom offers her a ride. Tom's pickup starts failing and Claire needs to keep in constant contact with Lorenzo but doesn't have reliable cell phone service. But their biggest issue might be their outward differences, which each assumes makes the other unsuitable for each. But Hilly can see that feelings are developing between them. Even if one or both would acknowledge those feelings, the fact of Claire's impending wedding may prevent a happily-ever-after for her and Tom.