Pilgrims to Rome headed down Via Romana leaving Florence behind them. The end of the road is marked by the Porta Romana, an imposing gate that was part of the outer circle of city walls knocked down in the 19th century. A strip of this wall still stretches to the north from the gate.
If you head along the inside of this wall (the area is now a car park), you will find an entrance that allows you to get to the top of the Porta Romana. The square below was traditionally a fairground for peasants in the surrounding county (contado) . By far the most curious of these fairs was the Fiera dei Contratti (Contracts Fair), when country folk from near and far dragged sons and daughters along to contract marriage. They would haggle keenly over dowries and, much to the amusement of the not-too-respectful city folk who had taken the day off to come and gawk, compel prospective brides to walk up the hill towards the Poggio Imperiale to see how well they swayed their hips!