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Crete Senesi
The Crete Senesi refers to an area in the south of Siena, which consists of a range of hills and woods among villages and including Asciano, Buonconvento, Monteroni d'Arbia, Rapolano Terme and San Giovanni d'Asso, all within the province of Siena. Crete senesi are literally ‘Siennese clays’ and the distinctive grey coloration of the soil gives the landscape an appearance often described as lunar. This characteristic clay, known as mattaione, represents the sediments of the Pliocene sea which covered the area between 2.5 and 4.5 million years ago. In the nearby is also the semi-arid area known as Accona Desert. The area suffered extreme depopulation due to plagues in the Middle Ages, and the attendant prolonged lack of cultivation facilitated an almost complete erosion of the topsoil. It was later settled by Sicilian farmers adept to cultivating cereals on less than optimal conditions, and who were able to establish sustainable cultivation of wheat on the Siennese clays.

Monte Oliveto Maggiore (Asciano, Siena)
One of the most notable edifice of this area is the monastery of Monte Oliveto Maggiore.The Abbey is a large Benedictine monastery and its buildings, which are mostly of red brick, are conspicuous against the grey clayey and sandy soil of the Crete senesi.It is a territorial abbey whose abbot functions as the bishop of the land within the abbey's possession, even though he is not consecrated as a bishop. It is the mother-house of the Olivetans and the monastery later took the name of Monte Oliveto Maggiore ("the greater") to distinguish it from successive foundations at Florence, San Gimignano, Naples and elsewhere.

Montalcino (Siena)
Montalcino is a hill town famous for its Brunello di Montalcino wine. The town is located to the west of Pienza, close to the Crete Senesi in Val d'Orcia and 42 km from Siena. 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 Its first mention in historical documents in 814 AD suggests there was a church here in the 9th century, most likely built by monks who were associated with the nearby Abbey of Sant'Antimo.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 population grew suddenly in the middle of the tenth century when people fleeing the nearby town of Roselle took up residence in the town. 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. The lower slopes of the Montalcino hill itself are dominated by highly productive vines and olive orchards. During medieval times the city was known for its tanneries and for the shoes and other leather goods that were made from the high quality leathers that were produced there. As time went by, many medieval hill towns, including Montalcino, went into serious economic decline, which has recently been reversed by economic growth due to the increasing popularity of the town's famous wine Brunello di Montalcino, made from the sangiovese grosso grapes grown within the comune. The number of producers of the wine has grown from only 11 in the 1960s to more than 200 today, producing some 330,000 cases of the Brunello wine annually. Brunello was one of the first wines to be awarded Denominazione di Origine Controllata e Garantita (DOCG) status. In addition to Brunello di Montalcino, which must be aged five years prior to release, Rosso di Montalcino (DOC), made from sangiovese grosso grapes and aged one year.

Pienza (Val d'Orcia, Siena)
Pienza, a town in the Val d'Orcia between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism. In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes. Pienza was rebuilt from a village called Corsignano, which was the birthplace (1405) of Aeneas Silvius Piccolomini (Italian: Enea Silvio Piccolomini), a Renaissance humanist born into an exiled Sienese family, who later became Pope Pius II. Once he became Pope, Piccolomini had the entire village rebuilt as an ideal Renaissance town. Intended as a retreat from Rome, it represents the first application of humanist urban planning concepts, creating an impetus for planning that was adopted in other Italian towns and cities and eventually spread to other European centers. The rebuilding was done by Florentine architect Bernardo Gambarelli (known as Bernardo Rossellino) who may have worked with the humanist and architect Leon Battista Alberti, though there are no documents to prove it for sure. Alberti was in the employ of the Papal Curia at the time and served as an advisor to Pius. Construction started about 1459. Pope Pius II consecrated the Duomo on August 29, 1462, during his long summer visit. He included a detailed description of the structures in his Commentaries, written during the last two years of his life.

Montepulciano (Siena)
Montepulciano is a medieval and Renaissance hill town 70 km far from Siena. It is known world-wide for its fabulous wine. Wine connoisseurs consider its Vino Nobile among Italy's best. Montepulciano is also known for its pork, cheese, "pici" pasta (a thick, rough, chewy variant on spaghetti), lentils, and honey. 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 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, built 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.

San Gimignano (Siena)
San Gimignano is a small walled medieval hill town in the province of Siena mainly famous for its medieval architecture, especially its towers, which may be seen from several kilometres outside the town. The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area. While in other cities, such as Bologna or Florence, most or all of their towers have been brought down due to wars, catastrophes, or urban renewal, San Gimignano has managed to conserve fourteen towers of varying height which have become its international symbol. There are many churches in the town: the two main ones are the Collegiata, formerly a cathedral, and Sant'Agostino, housing a wide representation of artworks from some of the main Italian renaissance artists. The Communal Palace, once seat of the podestà, is currently home of the town gallery, with works by Pinturicchio, Benozzo Gozzoli, Filippino Lippi, Domenico di Michelino, Pier Francesco Fiorentino and others. From Dante's Hall in the palace, access may be made to a Majesty fresco by Lippo Memmi, as well as the Torre del Podestà or Torre Grossa, 1311, which stands fifty-four metres high.The heart of the town contains the four squares, the Piazza della Cisterna, the Piazza Duomo where the Collegiata is located, the Piazza Pecori and the Piazza delle Erbe. The main streets are Via San Matteo and Via San Giovanni, which cross the city from north to south.

Siena
The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited tourist attractions.Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice yearly. The Palio is a traditional medieval horse race run around the Piazza del Campo twice each year, on 2 July and 16 August. The event is attended by large crowds, and is widely televised. Seventeen Contrade (which are city neighbourhoods originally formed as battalions for the city's defence) vie for the trophy: a painted banner, or Palio bearing an image of the Blessed Virgin Mary. For each race a new Palio is commissioned by well-known artists and Palios won over many years can often be seen in the local Contrade museum. During each Palio period, the city is decked out in lamps and flags bearing the Contrade colours. Siena's cathedral (Duomo), begun in the 12th century, is one of the great examples of Italian Romanesque-Gothic architecture. Its main façade was completed in 1380. It is unusual for a cathedral in that its axis runs north-south. This is because it was originally intended to be the largest cathedral in the world, with a north-south transept and an east-west nave, as is usual. After the completion of the transept and the building of the east wall (which still exists and may be climbed by the public via an internal staircase) the money ran out and the rest of the cathedral was abandoned. Within the Sacristy are some perfectly preserved renaissance frescos by Ghirlandaio, and, beneath the Duomo, in the baptistery is the baptismal font with bas-reliefs by Donatello, Ghiberti, Jacopo della Quercia and other 15th century sculptors. The Museo dell'Opera del Duomo contains Duccio's famous Maestà (1308–1311) and various other works by Sienese masters.

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