The legend of the Pulcinella Tower in Montepulciano has it that this was brought here by a bishop of Neapolitan origins, but since there was no figure of this type in the history of the village, more likely it was a priest. In 1524, in fact, a statue inspired by the "Mangia" of Siena was placed on the clock tower of Montepulciano with the task of marking the hours, but due to the deterioration suffered by the same, already in 1680 there was a first restoration and, on that occasion, presumably on the proposal of the priest (or in any case of a benefactor) of Naples, the automaton was covered with the colors of Pulcinella. According to some, however, this character was chosen as a tribute to the Theater.

Next to the Clock Tower is the white facade of the church of Sant’Agostino, of which the tower is part. Built earlier than this (in 1285), the church was renovated by Michelozzo himself in the sixteenth century and combines the neoclassical style of the Renaissance with the Gothic of the Middle Ages. Its front staircase has become, over time, a meeting point for many residents of Montepulciano.

coffees spread throughout the cities, and with the progress of bourgeois life they become more and more elegant and refined: even in the "minor" towns they take hold (we mention for all the beautiful Caffè dei Costanti in Arezzo, still today the meeting place of “chic” youth) and of course Montepulciano is no exception. There is very little documentation found so far on the "coffee" in Montepulciano and this does not allow us to speak about it with full knowledge of the facts. The habit of sipping the drink in company (and not only that, of course) had long been well known to the police. Already at the time of the construction of the first Academic Theater in the Town Hall (1759), a space was provided for the coffee and the "diacciatine", ie sorbets, cool drinks, etc., which were served on the occasion of theatrical performances.

The Town Hall of Montepulciano overlooks Piazza Grande. The building was built in the 13th century in the Gothic style and renovated by Michelozzo during the 15th century. The similarity between the Palazzo Comunale di Montepulciano and the Palazzo della Signoria in Florence is striking, it was personally commissioned by Cosimo I dei Medici. The ground floor is covered in ashlar, while the rest of the facade is in travertine. The battlements of the terrace are in Guelph battlements. Worth seeing are the interiors with the well and the nineteenth-century tombstones. The Palazzo Comunale di Montepulciano is the seat of the town hall. From its tower you can see a splendid panorama: on clear days you can see, from the side of the Val di Chiana the pre-Apennine peaks, Perugia, Subasio, Lake Trasimeno with its islands, and the lakes of Montepulciano and Chiusi.