When Marie surprises the family with the news that she's treating them all to a two-week vacation to Italy, everybody loves the idea except Raymond. Not willing to let his sour mood spoil it for the rest of the family, Debra, Frank, Marie, Robert, and the kids go on their merry way and soak up the atmosphere, the sights, and tastes of the country.

Ray is complaining about the heat, Debra is getting tired of following Marie's strict schedule and of Ray's pessimistic attitude, Robert meets Stefánia's father, who is not thrilled with his daughter choice of man, and Frank is enjoying himself playing pétanque. After going on a long walk with his mother, Ray slowly starts to enjoy himself and appreciate where he is, no thanks to Marie.

Robert finds himself in the most unlikely position of having to choose between his girlfriend Amy, ex-wife Joanne, or Italian summer love, Stefánia. Robert decides that honesty is the best policy when it comes to his relationship with Amy, so he tells her about his recent reunion with ex-wife Joanne, which does not go over well with Amy. To make matters worse, when Amy runs to Debra for consolation, Debra mistakenly spills the beans about Robert's recent fling with Stefánia.

Robert gets a surprise visit from Stefánia, the woman with whom he fell head over heels in love when the Barones went on holiday in Italy. Robert's excitement over having his summer love Stefania so close quickly gives way to annoyance when he is witness to a few of her idiosyncrasies. Meanwhile, Stefania's father, who has accompanied her to America, has his own change of heart with respect to his feelings for Robert.

Marie gathers Robert's ex-girlfriends Amy and Stefánia and his police partner Judy, so they can dissect his character in an effort to help her better understand why her eldest son can't commit to a relationship. Unfortunately, Robert unexpectedly drops in and is forced by his mother to listen to his character being assassinated by the women as they discuss his relationship hang-ups.

Frank is so green with envy that he forces Marco to choose either Marie or him as a friend. Meanwhile, Ray sides with Frank because he doesn't approve of a married woman having a male friend.