During a high school field trip to Italy, Carly, a fiercely driven know-it-all, faces a challenge from her classmates: embark on a daring solo journey, with specific landmarks to hit and a strict itinerary to follow. Determined to prove her mettle, Carly accepts but soon finds herself wandering across the Italian countryside. Along the way, she becomes entangled in a whirlwind of mishaps and unexpected friction with the locals, unraveling the core of her tightly-wound persona. As Carly's path diverges from the expected she learns that true wisdom often comes from surrender. 

ITALY '99