In the enchanting backdrop of Florence in 1935, a distinguished group of English expatriates, known as the Scorpioni, gather for their cherished afternoon tea rituals. This diverse assembly of cultured women includes Arabella, an aspiring artist renowned for her eccentricity, and Mary Wallace (portrayed by Judi Dench), who also serves as the caregiver for young Luca. Their companionship extends to Luca's seamstress mother, who has recently passed away. With Luca's father, a prosperous Italian businessman, exhibiting a lack of interest in his son's upbringing, Mary steps in and turns to her Scorpioni friends for guidance.
Serendipitously, Elsa Morganthal, a wealthy American widow with a fondness for Luca's late mother, learns of the boy's plight and sets up a financial trust for him. This act of kindness receives a nod of condescending approval from Lady Hester Random, who reluctantly permits Elsa’s presence in their circle.
However, their peaceful gatherings become threatened as Italian Fascists attack their favored café, mirroring the rising anxieties within the expatriate community. As tensions heighten, the Scorpioni increasingly feel the squeeze of oppression, with Luca's father, fearing Italy’s impending alliance with Germany, opting to send him away to an Austrian boarding school.
Time progresses to five years later, and Luca returns to Florence with ambitions of becoming an artist, empowered by Elsa's trust fund. Yet, turmoil looms as the majority of British nationals are retreating, anticipating Mussolini's war declaration against Great Britain. Mary has now taken residence with Lady Hester and the remaining English hold-outs, all grappling with their uncertain futures.
While the United States maintains its peace, Elsa (played by Cher) and her bold American friend Georgie Rockwell, a pioneering archaeologist unafraid of her lesbian identity, find liberty from the war's constraints. Elsa seizes the chance to utilize Luca as a courier, facilitating the discreet delivery of forged documents and funds to secure the Scorpioni's relocation from their humble quarters to luxurious digs. Lady Hester, cloaked in delusion, triumphantly displays a newspaper photo of herself with the Italian dictator, believing this move was sanctioned by Mussolini himself.
Amid the chaos of the war, Elsa—a Jewish woman safeguarded from persecution due to her wealth and nationality—secretly collaborates with Italian Jews to create fake passports. She enlists the reluctant help of Luca, who harbors unspoken feelings for her, to deliver these vital documents, unknowingly complicating their relationship as she grows closer to Vittorio, an Italian lawyer. As the war intensifies by 1941, Elsa and Georgie find themselves interned alongside British women, grappling with the harsh realities of their situation.
Meanwhile, Vittorio, driven by deceitful intentions, absconds with Elsa's art collection and funds, plotting to betray her to the German Gestapo while pretending to offer her a false escape route to Switzerland. Consumed by jealousy, Luca keeps this vile treachery a secret from his friends Mary and Wilfred. However, the truth eventually surfaces when Mary learns of Vittorio's betrayal through Elsa's art dealer and confronts Luca, stirring his conscience.
With a shift in perspective, Luca decides to redirect his trust fund towards the Italian resistance movement, joining forces with Wilfred. Oblivious to the schemes against her, Elsa remains unaware of Vittorio's duplicity until Lady Hester, chastised by Mary for her unrestrained admiration of Mussolini, divulges the grim reality, promising her support for the scheme.
In a pivotal moment, Elsa confides in Luca about her past support for his mother during a challenging pregnancy, deepening their connection. As plans for their escape take shape, the urgency heightens with the British Army closing in on San Gimignano in July 1944. Together with Arabella and Georgie, the English women, including Lady Hester, valiantly defend their artistic heritage against German troops.
As the Germans retreat, San Gimignano remains largely untouched, a testament to the resilience of its community. The arrival of the Scots Guards ignites celebration, with Luca stepping into the role of their trusted interpreter. Despite orders to abandon their home, Lady Hester staunchly resolves that they will rebuild their lives in Italy.
In the aftermath of war, Mary beams with pride as Luca, now dressed in British military uniform, fulfills his father's dream of becoming an "English gentleman." The film concludes with a revealing glimpse into the fates of these characters, showcasing Luca's evolution into a gifted artist and an integral part of the narrative.
