Passing Porta del Ponte you arrive in Via Italia, a small road connecting the castle and the alleys further down.

Via Italia is the main street of Montemerano, it connects Porta del Ponte with Porta della Canonica, it is a paved road of about 100 meters in length, which houses shops and shops, and is an obligatory stop for all tourists.

The street also houses one of the most famous restaurants in Italy, the “Trattoria Caino“.

Along the way you come across the doors of the underground cellars of Montemerano and the characteristic closed porticoes, which were once part of the Market Square.

Numerous alleys branch off from Via Italia, some of which are blind and end up against the city walls, while others reach enchanting little squares, such as the Piazzetta del’Antico Frantoio, here once stood one of the many oil mills in the village today remembered among three imposing stone millstones, the Piazzetta di San Martino, surrounded by characteristic houses with flowered balconies, and the Piazzetta del Ritiro, more intimate and secluded.

This part of Montemerano is certainly the most intimate and protected of the village, it houses small corners to be discovered, arches, ancient doors and windows, a century-old wisteria that grows right above an opening in the city walls, used in the past for the passage of men and animals, up to the characteristic “Vicolo della Flanella”, so nicknamed because once upon a time the young people of the town cultivated their sweet adolescent loves there.