The city is famous for its Vino Nobile, one of the best wines in Italy. Situated high on a hill, the picturesque city should also be visited for its architectural attractions. Most of the historical buildings date from the gothic or renaissance periods, making the old town remarkable even for this part of the world. The Piazza Grande is considered one of the most beautiful squares of Italy.
Medieval village between two Renaissance cities
Monticchiello is a medieval village located off the beaten path and offering an panoramic view to the north. The best way to enjoy the town's beauty is to approach it on foot via the old Strada Panoramica, which is now a hiking trail from Montepulciano to Pienza. The best place to stop for a bite to eat is in Monticchiello at the osteria there. (3:30 hrs, 12 km, elevation change: 290 m)
Fine example of Renaissance urban planning
This city was is one of the earliest examples of Renaissance urban planning. Its founder and namesake was Pope Pius II, who wanted to construct an “ideal city.” The central Piazza Comunale is framed by the cathedral, the courthouse and two Palazzi. From here, the streets fan out in all directions. Photographers from all over the world like to use the Terrapille in the southwestern part of town as a postcard motif for classic Tuscany. Part of the movie “Gladiator” was shot here in 1999. The 1969 movie “Romeo and Juliet,” which won two Oscars for best picture and best costume design, was filmed at the cathedral square and at the Palazzo Piccolomini.