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The Oltrarno - or Ultrarno, as it was called - was first estabilished around the 13th century, when only the Santo Stefano bridge (later renamed PonteVecchio) existed. On the other side of the river there was a wide open space with fields, vineyards and olive groves called Caselline (small houses) or Da la Cuculia

Santo Stefano bridge, in Oltrarno gave access to Borgo di Piazza, the present-day Via Guicciardini, going towards Via Romana and towards Borgo San Jacopo, and Borgo Pitiglioso (Via de" Bardi) to the east. In the south you could find the Bogule hill (Boboli) and then the Costa up to where the Rubaconte bridge was built (now called Ponte alle Grazie). Another bridge, called the New Bridge (Ponte alia Carraia) had been built a few years earlier at the location of the present-day Via de' Serragli. In the middle of the 13 century, Aldobrandino, an Augustinian monk from the Monastery of San Matteo in Arcetri, bought a piece of land with a vineyard and a well in the area of Caselline, sparsely inhabited at the time. He intended building a Monastery and a Church dedicated to the Virgin, the Holy Spirit and All Saints.  

Work on the building started in 1252. The houses in front of the building were purchased and demolished to make space for Piazza Santo Spirito. We think the Church was in the same place and had the same orientation we can see today. It probably had a nave and two aisles and a portico on the facade. At this time the town was experiencing great economic growth due to the expansion of trades and the minting of the first gold coin: the Florin. Craftsmen, labourers but also wealthy families started to move to the area of Caselline, and the Oltrarno gradually became more and more important. In the same period the Augustinian Monastery and Church were being erected, the Santa Trinita bridge and the largest road in the city, Via Maggio (which comes from "Maggiore") were built This consequently stimulated the development of the neighbouring area which became wealthy and popular. The name of Canto alia Cuculia brings to mind the original name given to this place. This explains why Bicci di Lorenzo painted a cuckoo held by the Child on the Virgin's lap in the shrine on the corner between Via de' Serragli and Via Santa Monaca. Apparently "Cuculia" (the term "cuculiare" meant to tease) hinted at the sarcasm with which foreign craftsmen were addressed. Florentines in fact believed that these outsiders were exploiting the rich resources of the district, behaving like cuckoos which lay their eggs in the nests of other birds. The wool industry was very active in this area. In fact the name of Via delle Caldaie brings to mind the large copper pans used to dye woollen fabrics. Via Sant'Onofrio was named after the Patron Saint of the "gualcherai" (the workers who pressed woollen fabrics) and dyers. Via and Piazza delTiratoio remind us that this square originally consisted of a building with a covered terrace which was used to beat, stretch, and dry the dyed fabrics. The building had been built in compliance with a law that prohibited these activities on the streets and on the roofs because the dripping dye used to stain walls and public spaces. Borgo Tegolaio, instead, takes its name from the building materials that were produced in the area, from the clay excavated from the Arno. Via delle Fornaci tells us that vase manufacturing laboratories were located along this street. The square was used by the Augustinians preaching. The Monastery of Santo Spirito soon became an important cultural centre in Florence up to the first decades of the 15'' century. The seat of the "Studio Generate" of the Order was in the Monastery, an institute devoted to the study of philosophy and theology that welcomed students from the most important European cities. Besides being used for preaching purposes, the square also played host to the corn market, as well as on the other side of the river where it was held in the famous Orsammichele.