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Situated in central-southern Tuscany, the Province of Siena extends over some of the most famous and fascinating Tuscan territories, e.g. the southern hills of Chianti, Val d’Elsa and Val di Merse, Val d'Arbia, Val di Chiana and Val d'Orcia, right up to the slopes of Mount Amiata. 

The Province’s Capital, Siena, is a magnificent city of art with characteristic alleys, wards (rioni) and towers, artisan shops and buildings that make it a not-to-be-missed touristic destination for Italians and foreigners. Moving through Siena’s lands and immersing yourself in this atmosphere is a magical adventure, a trip through many landscapes, from dense woodlands to old farms, from clay hills to stupendous paths. 

Furthermore, the territory preserves numerous remains from the Middle Ages, springing out along the Via Francigena, the great pilgrimage road to Rome that crossed Val d’Elsa, the city of Siena and Val d’Orcia. 
Walking through this countryside, you can admire impressive abbeys such as Sant’ Antimo, Romanesque parishes (pievi) and characteristic small towns (borghi) such as San Quirico d’Orcia or San Gimignano, which preserve their original appearance to this day. 

The Chianti area, home to the famous wine, is also an enchanting part of Tuscany that hosts tucked-away towns such as Castellina, and dense vineyards, such as those of Radda in ChiantiGaiole in Chianti or Castelnuovo Berardegna, as well as delicious enogastronomic itineraries. 
The landscape south of Siena leading towards the Medieval center of Asciano is dominated by the typical Crete, clay lands where erosion has created crevices, openings and cracks. It is an impressive area where the imposing Abbey of Monte Oliveto Maggiore stands out. Val d’Elsa is also very impressive with its characteristic towns Colle di Val d’ElsaPoggibonsi and San Gimignano, that boasts inestimable artistic heritage. 

Val di Merse is constituted of solitary but fascinating places, including the ruins of the San Galgano Abbey that date back to the 13th Century. Val di Chiana provokes emotion and offers its visitors elevated health and well-being, thanks to its thermal spa centers in Chianciano TermeMontepulciano and San Casciano dei Bagni
Hills and gullies, Tuscan cypress trees, the river, olive groves and vineyards: this is the landscape animating Val d’Orcia, protected by UNESCO. Here magnificent towns abide, from Pienza and San Quirico to Montalcino and Castiglione; in the west lie Mount Amiata and the solitary Rocca di Radicofani

The first leg of the itinerary leading to the discovery of the territory is Siena, the city famous for its Palio and listed as World Heritage by UNESCO for its singular artistic heritage. 
The historical center is dominated by Piazza del Campo, one of the biggest Medieval piazzas. It is shell-shaped and is the stage for the famous Corsa del Palio (Silk banner horserace). Here stand monuments of great value, such as the 13th-14th-Century Palazzo Pubblico (the town hall), a true jewel of the Gothic and home to the Civic Museum; the Piazza Chapel, upon which stands the bell tower, Torre del Mangia, and Jacopo della Quercia’s marvelous Gaia Fountain (in actual fact, the Piazza holds a copy, while the remains of the original are preserved in the Museum Complex of Santa Maria della Scala). 

One of the city’s numerous art treasures is the Duomo (12th-14th century), one of the highest expressions of Romanesque-Gothic art, abounding in sculptures, paintings and works of architecture, also home to the Opera Metropolitana Museum, exhibiting masterpieces by famous artists such as Duccio di Buoninsegna, Ambrogio Lorenzetti and Taddeo di Bartolo. Two other of the city’s art treasures are the imposing Medici Fortress in red brick, commissioned by Cosimo I in the mid-16th Century and the elegant Loggia della Mercanzia, a transition architectural work from Gothic to Renaissance style.

A place of great devotion is the House and Sanctuary of St. Catherine of Siena, the Patron Saint of Italy and Europe. The structure, built around the house, comprises chapels and cloisters richly-decorated by various artists. 
Not to be missed is the Pinacoteca Nazionale housed in the elegant Palazzo Buonsignori, featuring a collection of 13th-16th-Century works of the Sienese school. 
In addition to the marvelous City of Siena, not to be missed are the Crete and the Natural and Cultural Artistic Park of Val d’Orcia, listed as a World Heritage Site by UNESCO for the beauty of its landscape and an inspiration to many Renaissance artists. Here stands a city of particular importance, Pienza.
It too is recognized by UNESCO as a World Heritage Site for the wealth of its monuments and its rational organization of space and perspective. Pienza is the “ideal city,” created upon the wish of Pope Pius II for a city built according to Renaissance ideals. 

In the Val di Chiana area lie other delightful towns. Montepulciano is located upon a hill from where it dominates the valley, with its rising and falling slopes in a typically-Medieval atmosphere. Chianciano Terme is important for its beneficial waters that were famous as far back as Etruscan times, and is home to the beautiful Museo Archeologico delle Acque (Water Archaeological Museum). Chiusi is a small town with an internationally-reputed Etruscan museum. 
In Val d’Elsa, charming are Monteriggioni and San Gimignano, also called the "city of towers" for its numerous towers and tower-houses that render its skyline quite unique; it was the symbol of Medieval mercantile power. This characteristic Medieval borgo, under the tutelage of UNESCO, boasts a remarkable artistic legacy, including the marvelous Collegiata (13th Century), the Gothic-Romanesque St. Augustine’s Church and the Palazzo del Popolo - site of the Civic Museu, upon which stands the Torre Grossa (Big Tower). 
Other characteristic towns abound in the Sienese territory: of particular ntoe is Montalcino, home to the famous Brunello wine, and the nearby St. Antimo's Abbey, a splendid example of Romanesque-Tuscan style with Lombard influences. 

The Province’s marvelous and unique landscapes offer infinite opportunities for outings on footcycling excursions and horseback riding, or even hiking in diverse settings, from the clay lands of the Crete, the numerous woods or the cultivated countryside. Ski enthusiasts will be able to try out the winter sports hub at Mount Amiata, the most important in the territory. 

For those that enjoy close contact with nature, there is no lack of Natural Reserves, with the Province counting 14 of its own. In the Province's south is the Reserve of Lake Montepulciano, offering up plenty of rare bird species; that of Lucciola Bella, with a splendid view over Val d'Orcia; and that of Pietraporciana, inside a centuries-old beechwood forest. 
Food enthusiasts can follow enogastronomic itineraries through vineyards, olive groves and small hamlets, stopping off at farms and wine bars to taste typical products and excellent local wines. 
The territory has many thermal spa centers where you can spend relaxing, health-focused stays, in Bagni di San FilippoBagno VignoniChianciano TermeRapolano Terme and San Casciano dei Bagni

The local calendar is rich in events and activities: the unmissable event is the Palio di Siena, one of the most popular and highly-anticipated traditions on the Italian calendar. The various contrade (neighborhood zones) of the city challenge each other in this joust of Medieval origins, twice a year in Piazza del Campo, on July 2nd and August 16th. The Palio is preceded by an historical procession revoking the wealth and independence of the Republic of Siena. Originated from medieval jousts and games it has been taking place since the 16th Century. 

In Piazza Grande, in Montepulciano, the Bruscello is a festival of love stories in the Tuscan tradition; players dressed in costume narrate them on a stage decorated with a symbolic tree. In Torrita di Siena, in March, the San Giuseppe Festival is held, where eight contrade compete for the Palio dei Somari (a donkey race) dressed in 17th-Century costumes. The Medieval folklore carries on in Montepulciano, with the renowned combat of the Bravio delle Botti in August, during which the athletes representing the contrade compete by pushing heavy, 176-lb barrels. In Monticchiello rather, between July and August, the entire community participates in ten days of not only horseback riding, but in writing and producing a drama focused on the issues of rural life.

Then, the Sagra of San Giuseppe is held in Torrita di Siena in March, during which representatives of the eight contrade compete for the Palio dei Somari. In Asciano, in the month of September, the Palio dei Ciuchi (yet another donkey race), features each of the town’s contrade, also in Medieval attire. Worth a visit are also the Medieval Barbarossa festival in San Quirico d’Orcia in June, and the Sagra del Tordo (Thrush Fair) in Montalcino, in October. Finally, the spectacular Giostra del Saracino (The Saracen Joust) is held in Sarteano on the Feast of the Assumption (15 August). 

The Sienese cuisine is based on natural flavors and aromas, making abundant use of garlic and aromatic herbs like wild fennel and tarragon. The area is also home to producers of one of the best extra-virgin olive oils in Italy. Typical delicacies are pici (thick, handmade spaghetti), ribollita (a vegetable and bean soup) served with bruschetta, mixed roasts, stewed or grilled game, cacio pecorino, Val di Merse's minestraccia (a bean and vegetable dish), mushrooms, Val d’Elsa tripe and Monticiano wild boar, and cold cuts made with the Cinta Senese, the famed black pig with a white stripe, depicted in some famous 15th-Century paintings.

And then, how can we not mention the Chianina cow that is the biggest bovine in the world for dimensions. 
The excellent local wine production includes five DOCGs: Chianti Colli Senesi, Chianti Classico, Vernaccia di San Gimignano, Brunello di Montalcino and Vino Nobile di Montepulciano, the first wine to be assigned the DOCG certification. Moreover, the Province of Siena produces three types of high quality extra-virgin oil: Chianti Classico DOP, Terre di Siena DOP and Toscano IGP.