Going past Porta del Ponte you arrive in Via Italia, a small road connecting the castle to the alleys below.

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

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

Along the way there are the doors of the underground cellars of Montemerano and the characteristic closed arcades, once part of the Piazza del Mercato.

Numerous alleys branch off from Via Italia, some of them are blind and end up against the walls, while others reach enchanting squares, such as the Piazzetta del’Antico Frantoio, here once was one of the many oil mills in the village today remembered among three imposing stone millstones, the Piazzetta di San Martino, surrounded by the 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 preserves small corners to be discovered, arches, ancient doors and windows, a centenary wisteria that was born right above an opening in the walls, used in the past for the passage of men and animals, up to the characteristic “Vicolo della Flanella”, so nicknamed because once the young people of the town cultivated their sweet adolescent loves.