The route crosses some of the city centre streets and those adjacent to it, just outside the city walls characterized by the evocative gateways to the city.
Leaving Piazza del Campo, head eastbound, immediately coming to the Logge del Papa, a lodge dating back to 1462 next to the church of San Martino with the typical Baroque facade, and continuing to Porta Romana, built in 1327. After passing it, you will find in the ancient Via Cassia for a short distance.
Turning left, you arrive at Porta Pispini, erected in 1326 and flanking the walls for over one kilometre. You can enter from Porta Ovile, built in 1246, and going up the road you will find the fourteenth Century Fonte Nuova, one of the city’s oldest water springs.
Pedaling for a slight ascent, you will come out of the walls of the Barriera di San Lorenzo and find Porta Camollia, the northern entrance to the city, dominated by the famous inscription “Cor magis tibi Sena pandit” (Siena opens up a bigger heart to you…than the threshold you are crossing).
Descending for about a kilometre, you arrive at the Pescaia picnic area where you can stop, fill up your water bottle and do some exercise with the public gym equipment. Then, cycle for about four kilometres to reach a very panoramic area of the route and re-enter the historical centre through Porta San Marco, which dates back to 1325, and after a few hundred metres of slight ascent, you will reach the ancient paved streets of the city to return to Piazza del Campo from Via del Casato.