Via Maestra is the main street of the historical center, running between medieval and Renaissance palaces that once belonged to the most powerful Florentine families. Tourists can catch a glimpse of the terrace of the ancient Ricciardi house, one of the properties that belonged to the owners of the Strozzavolpe Castle. This castle lies outside of the city’s residential center, amidst lush vineyards and a beautiful ochre yellow and azure blue countryside.
Moving outside of the center, one will find ample street art to admire, located in various points throughout the city. Thanks to innovative contemporary art projects, the city displays beautiful art from a wide range of artists, including Anthony Gormley and Mimmo Paladino.
When leaving the center, visitors will stumble upon gems like the splendid neo-Gothic castle of Badia and the Church of San Lucchese.
Along Via Francigena, one of the first spots that visitors will come upon is the Fonte delle Fate fountain. This spot is a wonderful remnant of Poggibonsi’s medieval origins, when it was founded by Florentines in 1270. There is also an important work of art inside this fountain, I Dormienti, the Sleepers, by Mimmo Paladino.
Further outside of the city center lies the Fortress of Poggio Imperiale, which was built in a unique architectural style imagined by Francesco di Giorgio Martini as part of his vision of an ‘ideal city.’ The Cassero and Piazza d’Armi can be found inside the perimeter walls.
Visitors can rest here, stopping to look at Monte Maggio and Monte Amiata, and to take in the sweeping view of hills stretching out to the sea.
Upon exiting the fortress, visitors will arrive at the Archeodromo, where they can see how history unfolded, from 5th-century settlements, including a Lombard village, to a ‘curtis,’ a sort of farming community constructed around the longhouse of the local lord. Now the “true” landlords of this place are its people and its territory, bridges suspended between tradition and contemporaneity.