Piazza Santa Maria Novella, with its original five-sided shape, is one of the largest squares in the old city centre of Florence: it was in fact enlarged several times to be able to contain the crowds of people drawn there by the preaching of the Dominican monks, who had settled in this part of town in 1221 and built a convent. The size of the square was later to make it the obvious place to hold the Palio dei Cocchi or Chariot race, today only recorded by two marble obelisks set on top of two bronze turtles by Giambologna.

One side of the square is occupied by the Dominican Basilica and the area containing the convent, which also included the monks' ancient Pharmacy, while another is delimited by the long loggia of what was once the Hospital of San Paolo, built between 1489-96 as a copy of the Loggia degli Innocenti by Brunelleschi. A polychrome terracotta lunette by Andrea della Robbia, who also created the tondos placed between the arches, can be seen on the right underneath the portico. The lunette depicts a meeting between St. Francis and St. Dominic, which is said to have taken place here in 1221.