The city is constructed along a ridge, which varies in level of between 50-60 metres and is reflected along the 1½ kilometres of main central street, that starts at the Porta al Prato and goes up to the Piazza Grande: the houses are arranged along the main street and in a series of short and narrow streets, often steep and more or less perpendicular. 

Almost all the buildings of major importance appear along the main street and constitute a long series of façades almost like an exhibition of high level design.

Montepulciano has known two building booms, one particularly significant in the 16th century and the other during the successful years between the 17th and 18th centuries. During the 1500's there was a particularly heavy urban development, limited in part to the noble families of the city who planned and realized the new façades, thus bestowing prestige on the owners: the construction outside the gate of the imposing Temple of San Biagio that was designed by Antonio da Sangallo The Elder, who created a 'style' and who reconstructed, to a great extent a source of local workers, who built the Palaces of Avignonesi, Cocconi, Cervini, Gagnoni-Grugni, Contucci and Tarugi, to mention only the principal ones, also they completed many many buildings that to Montepulciano are considered minor but would be 'major' in many other parts (remember the Bellarmino Palace and the palace of the ex-seminary where there is the seat of the Mosaic School, in Via Talosa, for their beautiful courtyards). The second period saw the presence and influence of the celebrated architect Frà Andrea Pozzo, a Jesuit, who left to Montepulciano the impressive Gesù Church, with a particular almost circular plan, the reception room of the Contucci Palace with its perspective effects, and the numerous interiors that he redesigned: the Santa Chiara outside the walls and the Church of Santa Maria above all, have examples of this sober and legendary late baroque style.Another group of buildings that were constructed in the architectural style of the late 1500's and worthy of observation are: the Cathedral, with its bare interior, where and architectural game has been played with line and form, built by Ippolito Scalza from Orvieto (1532-1617), also the Piazza delle Erbe Loggia and the church of the Madonna delle Grazie, traditionally attributed to him. We have purposely left for last the two famous buildings of the 1400's, the Palazzo Communale (Town Hall) and the Church of Sant'Agostino, of which are juxtapose humanist and late gothic elements, both works of Michelozzo di Bartolomeo; and to finish the Temple of San Biagio, the imposing sanctuary with a central plan on a Greek cross, a façade with two bell towers (one incomplete) and a perfect dome, serving as an example of the architectural theory of the Renaissance; perhaps the main work of Antonio da Sangallo the Elder and providing a perfect font of inspiration for the new St. Peter's of the Vatican by Antonio da Sangallo the Younger.
The architectural and artistic achievements in the municipal territory cannot be compared with that of the capital; the small centre of Valiano, situated on a small hillock where there is the Master Canal of the Chiana, which is particularly fascinating, and enjoys a splendid panorama of the Valdichiana to the west and to the hills of Cortona in the east.
Very suggestive are the two hills of Totona that face the capital and that of the Cappuccini, which is a short distance to the south: covered with woods and with routes and ascents providing impressive views. TOP