The main character of The Smile by Donna Jo Napoli is Elisabetta, who is the daughter of a silk merchant outside Florence, Italy during the Renaissance. There is a subplot where Elisabetta is friends with a young servant named Silvia. Elisabetta's parents keep pressing her to end her friendship with the servant. Later on in the story, Silvia becomes important to the plot. Once when Elisabetta's family attends the funeral of the ruler and banker of Florence, Lorenzo de'Medici Il Magnifico, Elisabetta tours the city with her father's friend, Leonardo da Vinci. He promises to paint her portrait when she is older. Elisabetta meets Lorenzo's youngest son, Giuliano. They fall in love. Then the French army masses outside the gates of Florence because the city is an ally of France's enemy, Naples. The citizens support France, because Florence is one of the financial capitals of Europe, and the French were financially powerful at that time. The Florentines accuse the ruling Medici, Piero of being a tyrant and banish the family from the city. Will the love between Elisabetta and Giuliano survive the political turmoil? Will Elisabetta's friendship with Silvia survive? Finally, what does this have to do with the portrait da Vinci is going to paint of Elisabetta?