La The church of Saint Francis is home to many paintings dating back to different historical periods, which confirm the strong bonds of the Order of Friars Minor with Mary and clearly illustrate the evolution of Marian iconography in time. The oldest image of the Blessed Virgin is a fresco taken from the friary walls and currently found in the Martinozzi Chapel in the right wing of the transept. The work, painted by Sienese artist Lippo Vanni in the second half of the fourteenth century, recreates the structure of a polyptych: The Blessed Virgin with Child, together with four Saints, are in the centre; above there is the Blessing Christ with the four Fathers of the Church, while the predella portrays a Pietà, with Christ cradled by Mary and St. John, flanked by figures of prophets.The Blessed Virgin holds the Child who embraces her lovingly while playing with his Mother’s veil. This representation of the Blessed Virgin, known as "Eleousa", the Merciful, is one of the oldest and most popular ones in the Middle Ages. The artist lays emphasis on the human side of the two figures: Jesus is portrayed as a lively child who looks straight at the observer, while the Blessed Virgin’s tightened lips and melancholy gaze echoes her awareness of her Son’s tragic fate.

However the Virgin and Child are not always depicted in such a natural manner; sometimes artists gave them a . . .