The aforementioned fortress of Poggio Imperiale is part of the Archaeological and Technological Park, created to detail the story of the hill's past through the different phases of human settlement, starting with the villages made up of early medieval huts. The route includes a walkway along the walls from which you can admire a unique landscape that includes the towers of San Gimignano, while the Cassero houses the Documentation Centre that reconstructs the history of the site with explanatory panels, finds and reproductions of objects and clothes of the era. If you suddenly find yourself in front of knights who are training to strike swords or if in the distance you see smoke rising from some hut, it's a sign that you have entered the area of the park called the Archeodromo, consisting of a faithfully reproduced 10th century village brought to life by blacksmiths, cooks, farmers and spinners.
On the same theme, there's the Museum of Paleontology, set up inside the medieval Palazzo Pretorio and divided into three sections: Paleontology, Evolution of Humankind, Archaeology and Natural History (with the ruins of a Neolithic age Cucule tomb).
Among the buildings of the city, don't miss the Sanctuary of Romituzzo, a historic place of worship dating back to the 14th century, in which anatomical ex votos and painted tablets are preserved, and the Collegiate Church of Santa Maria Assunta which is the largest of the area.
Finally, there's no lack of contemporary art, with the cast iron statues that Anthony Gormley made from casts of Poggibonsesi citizens located in various areas of the city, as well as the sculptures of crocodiles and sleeping men by Mimmo Paladino, placed at the bottom of the beautiful medieval springs.