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Montalcino is located to the west of Pienza, close to the Crete Senesi in Val d'Orcia. The hill upon which Montalcino sits has been settled probably since Etruscan times. Its first mention in historical documents in 814 AD suggests there was a church here in the 9th century, most likely built by monks who were associated with the nearby Abbey of Sant'Antimo. The town takes its name from a variety of oak tree that once covered the terrain. The very high site of the town offers stunning views over the Asso, Ombrone and Arbia valleys of Tuscany, dotted with silvery olive orchards, vineyards, fields and villages. During the late Middle Ages it was an independent commune with considerable importance owing to its location on the old Via Francigena, the main road between France and Rome, but increasingly Montalcino came under the sway of the larger and more aggressive city of Siena.
The first medieval walls were built in the 13th century. The fortress of Montalcino is one of the most visited sites in the town. The fortress was built at the highest point of the town in 1361, on a pentagonal plan designed by the Sienese architects Mino Foresi and Domenico di Feo. The walls include the tower of San Giovanni and an ancient basilica which now serves as a chapel.
Down the narrow, short street that extends from the main gate of the fortress is the Chiesa di Sant'Agostino with its simple Romanesque façade, also built in the 13th century.
The building adjacent to the church is a one-time convent, but it is now the home of the Musei Riuniti which is both a civic and diocesan museum. The museums hold various works, including a gorgeous wooden crucifix by an unknown artist of the Sienese school, two beautiful 15th century wooden sculptures and several other sculptures in terracotta which appear to be of the Della Robbia school. The collection also includes a St Peter and St Paul by Ambrogio Lorenzetti and a Virgin and Child by Simone Martini.
The Duomo (cathedral), dedicated to San Salvatore, was originally built in the 14th Century, but it now has a neo-classical appearance thanks to extensive renovation work that was done in the early 19th century under the direction of Sienese architect Agostino Fantasici.
The main piazza, the Piazza del Popolo, is downhill from the fortress and Duomo on the via Matteotti. The principal building on the piazza is the town hall, once the Palazzo dei Priori (built late 13th, early 14th century) but now the Palazzo Comunale. The palace is adorned with the coats of arms of the Podesta who once ruled the city. A very high medieval tower is incorporated into the palazzo. Close by is a Renaissance structure with six round arches, called La Loggia, which was started at the very end of the 14th century and finished in the early 15th, but which has undergone much restoration work over the subsequent centuries.
Montalcino is divided, like most medieval Tuscan cities, into quarters called contrade. The thirteenth-century church of San Francesco in the Castlevecchio contrada has undergone several renovations. Some of the interior frescoes were done by Vincenzo Tamagni in the early sixteenth century.

Montepulciano, is built along a narrow limestone ridge and, at 605 m (1950 ft) above sea level, between Val D'Orcia and Val di Chiana. The town is encircled by walls and fortifications designed by Antonio da Sangallo the Elder in 1511 for Cosimo I. Inside the walls the streets are crammed with Renaissance-style palazzi and churches most of which are located along the main street, called the Cordo that climbs up into the main square, Piazza Grande, which crowns the summit of the hill. The Corso is about 2 km long and offers a long procession of facades, almost an "exhibition" of high level architectural design.
The name of Montepulciano derives from Latin Mons and Publicianus ("Mount of Publicianus"). According to legend, it was founded by the Etruscan King Porsenna of Chiusi.

The main street of Montepulciano stretches for 1.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill. The city is renowned for its walkable, car-free nature. The main landmarks include:
The Palazzo Comunale, designed by Michelozzo in the tradition of the Palazzo della Signoria (Palazzo Vecchio) of Florence.
Palazzo Tarugi, attributed to Antonio da Sangallo the Elder or Jacopo Barozzi da Vignola. It is entirely in travertine, with a portico which was once open to the public.
The Cathedral of Santa Maria Assunta, or the Duomo of Montepulciano, constructed between 1594 and 1680, includes a masterpiece from the Sienese School, a massive Assumption of the Virgin triptych painted by Taddeo di Bartolo in 1401.
The church of Santa Maria delle Grazie (late 16th century). It has a simple Mannerist façade with a three-arcade portico. The interior has a single nave, and houses a precious terracotta altar by Andrea della Robbia.
The Sanctuary of the Madonna di San Biagio is on the road to Chianciano outside the city. It is a typical 16th century Tuscan edifice, designed by Antonio da Sangallo the Elder on a pre-existing Pieve, between 1518 and 1545. It has a circular (central) plan with a large dome over a terrace and a squared tambour. The exterior, with two bell towers, is built in white travertine.
The walls of the city were designed and built under the direction of Grand Duke of Florence Cosimo I de' Medici in 1511 by Antonio da Sangallo the Elder. (Cosimo I was born in 1519 and only became Duke in 1537 so this is not possible)
Also interesting to note while walking though the town is that Montepulciano is standing in for the Volturic Stronghold of Volterra in the film adaptation of the Stephenie Meyer novel New Moon, the second book in the popular Twilight Saga.

Podere Santa Pia, a formal cloister in the Tuscan Maremma with a view made in heaven is the perfect holiday resort for relaxing and enjoying the splendor of the Maremma hills of southern Tuscany. Podere Santa Pia enjoys a wonderful panoramic view of the Tuscan Maremma and is located near many cultural and historical places of interest, such as Pienza, Montalcino, San Quirico d'Orcia, Bagno Vignoni and many others.

Artist and writer's residency | Holiday houses in Tuscany | Podere Santa Pia