The most famous bridge in Florence and also the oldest, this structure with three stone arches replaced a wooden bridge which had crossed the Arno River at this spot since Roman times. The upper side of the bridge, known as the Vasariano corridor, was designed by Vasari to link the Palazzo Vecchio and the Uffizi Gallery to the Pitti Palace; today it is an art gallery.

The bridge is inhabited. Originally the sides held food shops but by the end of the 15th century the shops were assigned to goldsmiths and silversmiths. An opening midway across the bridge offers views of the river and shore.

The first merchants consisted primarily of blacksmiths, butchers, and tanners catering mostly to travelling soldiers not surprisingly. When half of the population perished with the Black Plague in 1348 those who survived began to question their old ways of living. Shortly after this period the Medici family moved into Florence bringing with them vast wealth as appreciation for the finer things in life.

When they acknowledged the use of the Arno by the merchants led to a grave degree of pollution of its waters, they decided to take action by replacing them with goldsmiths and artists and soon the number of shops greatly increased. Eventually between the years of 1565 and 1800 an upper level, as well as a back row of shops, was added which crosses the bridge and connects Uffizi Gallery with Palazzo Pitti.