Agriturismo Cesani San Gimignano - Siena Bed Breakfast La Fornace di Racciano  San Gimignano - Siena Le Caggiole farmhouse in San Gimignano La Lastra Siena Visit of vineyards
and cellar with wine tasting and light-lunch Relais della Rovere hotel relais colle val d'elsa Siena


Montalcino rises in the heart of southern Tuscany. In the Middle Age the territory of Montalcino was divided between four ecclesiastical areas: Arezzo, Chiusi, Grosseto and Siena.

Rocca di MontalcinoMontalcino rises in the heart of southern Tuscany. In the Middle Age the territory of Montalcino was divided between four ecclesiastical areas: Arezzo, Chiusi, Grosseto and Siena. This subdivision mirrored that of the antiquity, in fact here met the territories of the important Etruscan 'Lucumonies of' Arezzo, Chiusi, Roselle (Grosseto) and perhaps also of Volterra. Many recoveries of this time are today preserved in the Archaeological museum of Montalcino
The medieval history of this area is full of innumerable black holes, that's why the whole written documentation was preserved in the destroyed archives of the abbey of S.Antimo, from which the castle depended. Also the fact that the Francigena Road passed at east of the town, near the settlement of Torrenieri, didn't helped us to retrieve historical notices preceeding the second half of 12th century.


One of the town walls gates connected with the castle at the level of the S.Giovanni tower. 
The history that we know starts from the end of the 12th century, with the free town of Montalcino allied with Siena during the war of the 1176, lost, against Florence.
Montalcino offered resistence to the expansionists aims of Siena and the alliance was broken, consequently in the mid-13th century the castle was destroyed by the senese army, momentarily in peace with that Florentine (busy to eliminate the analogous obstacle constituted by Semifonte). The renewal of hostilities with Florence prevented the Senesi to complete the conquest of Montalcino but the castle remained under the protectorate of the Church and the Commune of Siena. After a rebellion attempt to conquer again its autonomy, in 1232 the castle was reoccupied and forced to a new alliance with Siena. After another insurrection in the 1252 the castle was conquered again by the Senesi but immediately lost due to the intervention in its help of Florence and Grosseto. To Montaperti battle  Montalcino lined up with Florence against Siena and the victory of this last didn't do anything else than bring the city to a new loss of autonomy. In 1269 Siena was again defeat at Colle Valdelsa and Montalcino was freed again. Only after half the 14th century the castle returned under the control of Siena. In this period the fortifications were reconstructed to better control the city center.

Rocca di Montalcino
The northeast tower.

By now Montalcino was Senese and in the 15th century became one of the most important centers of the Republic territory. In the following century the city and the castle withstand in 1553 the siege of the Medicean and Imperial army, during the war that brought Siena to the definitive capitulation of 1555. After the surrender many citizens of Siena reached Montalcino where, headed by Pietro Strozzi, let relive in exile the Republic. The city became the chief town of the territories not conquered by the Florentines and resisted until 1559 when, isolated by the fall of the castles of Talamone and Castiglione della Pescaia, offered its surrender and sworn fidelity to Cosimo de' Medici. 
The castle is today practically intact. Its construction was begun in 1361 on the southern vertex of the 13th century city walls, incorporating the keep of S.Martino and the S.Giovanni tower. It looks as classic castle-enclosure, with pentagonal plant endowed with towers to all the angles. The tower of southeast is placed by the side of the keep. The walls and the towers have still practicable the complete watch-walk endowed of machicoulis (projection from the wall made of stone which has openings through which the defenders can fire upon an enemy directly below) in stone, supported by bows on brackets with inverted pyramid form. The northern towers are open on the side facing the courtyard. The castle incorporated also an ancient little basilica that became the chapel of the fortification, and its rests are still visible near the northeast tower. On the south side rise the mighty Medicean rampart, added by Cosimo at the half of the 16th century.

Museo civico di Montalcino

Accommodations in the area

  • Agriturismo le Caggiole Farmhouse Montepulciano Siena Agriturismo le Caggiole
    Immersed in the verdant countryside around the noble town of Montepulciano, that boasts ancient Etruscan origins, Le Caggiole Estate is perfectly located for exploring Tuscany's most prized treasures.
  • Agriturismo Marciano Farmhouse Siena Siena Agriturismo Marciano
    Agriturimo Marciano : an exlusive opportunity, two holidays at the place of only one. stay in the country and life downtown. Marciano is located near the walls of the Middle Age town of Siena.
  • Agriturismo Catabbiaccio Farmhouse Semproniano Grosseto Agriturismo Catabbiaccio
    The farmhouse Castello di Catabbiaccio is located just 12 Km from Saturnia hot weather spa and 20 Km from important centres of etruscan civilisation like Sovana, Pitigliano and Sorano.
  • Relais della Rovere Relais Colle Val D'Elsa Siena Relais della Rovere
    The Relais Della Rovere is a charming hotel created from the conversion of an ancient Benedictine abbey and a papal villa of the Renaissance period.
  • Il Convento di Monte Pozzali Farmhouse Massa Marittima Grosseto Il Convento di Monte Pozzali
    The convent of Monte Pozzali is an ancient monastery dating from the 12th century which has been completely renovated into a welcoming country residence.
  • La Pieve Farmhouse Colle Val D'Elsa Siena La Pieve
    La Pieve, charming farmhouse located on the hills of Val d'Elsa, between Volterra and San Gimignano, along the Via Francigena, in the heart of the Tuscan countryside, with its luxuriant nature and rich history.
  • Agriturismo la Lucciolaia Farmhouse San Gimignano Siena Agriturismo la Lucciolaia
    In the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside, Agriturismo La Lucciolaia is perfectly located for exploring Tuscany's most prized art towns.
  • Agriturismo Villa il Palagetto Farmhouse San Gimignano Siena Agriturismo Villa il Palagetto
    Agriturismo Villa il Palagetto located in the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside.
  • B&B la Fornace di Racciano Bed Breakfast San Gimignano Siena B&B la Fornace di Racciano
    La Fornace di Racciano is a lovely Bed&Breakfast a short distance from the historical centre of medieval San Gimignano. It consists of a typical Tuscan country house surrounded by a large flowery garden.
  • B&B Giardino dei Sugheri Bed Breakfast Scarlino Grosseto B&B Giardino dei Sugheri
    Bed Breakfast Giardino dei Sugheri is located in Maremma Tuscany and is the result of a careful restructuring which gave new life to an old farmhouse in the heart of Tuscany.
  • Agriturismo Cesani Farmhouse San Gimignano Siena Agriturismo Cesani
    Azienda Agricola Biologica Cesani is an organic farm nestled in the rolling hills of the Tuscan countryside, in the tiny country hamlet of Pancole, 6 km to the medieval town of San Gimignano.

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