The development of Paganico, and its passage from little village to walled town, is strictly connected to the beginning of the Sienese domination on this area of the Maremma, started in 1193. The fortified strongold, placed at the confluence between the rivers Ombrone and Lanzo, was constructed along the main road that from Siena, passing through S.Lorenzo a Merse and Forcole, leads to Roselle and Grosseto, giving origin to a real 'terra nuova', a settlement straight in the heart of the new southern territories of Siena.

To facilitate the economic growth, Paganico was free of fiscal impositions and taxes, so that at the time was named Castelfranco Paganico. To increase its importance in 1294 the town was made seat of an important market to destabilize the feudal economic system of the zone, controlled by the Ardengheschi family. In order to complete the elevation of its rank, since 1303 Paganico was seat of a vicariate. The damages provoked by the mercenary troops and the nasty air of the Maremma, at that time a malarial swampy region, caused, starting from the mid-13th century, the depopulation of Paganico. In 1494 the town was sacked from the troops of Carl VIII° then it passed under the Medicean control but only with the Grand-Ducal drainages, carried on in the 18th century, the area known an economic and social rebirth.

The first walled enclosure of Paganico dates back to 1278 and was destroyed in the 1328 by Castruccio Castracani. Little after, in 1334, were erected the new town walls, under the direction of the architect Lando di Pietro, the same director of the works at the New Cathedral of Siena. These walls have the shape of an irregular quadrilateral, nearly trapezoidal, with squared towers on each curtain, four massive tower at the angles, four gates placed at the extremities of the two main road that crossed the town. Remnants of the machicolations are still partially visible. A tall keep or 'mastio' [called Cassero Senese, transformed in medicean age in a residential palace], flanks of the North gate, also known as 'Porta Senese'. The North and South Gates were equipped of a small barbican, now disappeared. The eastern front of the town walls with its Gate is nowadays totaly lost, together with some part of the northern, but all the other sides still surround the town, even though in some parts damaged. Intact are the 'Porta Grossetana' (or Franca) and the Porta Senese, both endowed with the characteristic pointed arch overlapping a lowered round arch surmounted by the black and white coat of arms of Siena. Partially intact is also the Porta Ovest.

Inside the town is geometrically laid out, as all the planned settlements, with some beautiful medieval mansion with porches and, in the main square, the recently restored well and the Romanesque church of S.Michele, erected between 1296 and 1305, with two cycles of frescoes attributed to Biagio di Goro Ghezzi.

The wide and enchanting landscape of the Val d'Orcia area became one of the Unesco World Heritage sites in March 2005. Here is the original justification reported in the Unesco web site: 'The Val d'Orcia is an exceptional reflection of the way landscape was re-designed in Renaissance times to reflect the ideals of good governance and to create aesthetically pleasing pictures. Painters from the Siennese School, which flourished during the Renaissance, celebrated landscape of the Val d'Orcia. Images of the Val d'Orcia, particularly depictions of landscapes in which people are shown living in harmony with nature, are now considered strongly representative of the Renaissance and have profoundly influenced the development of landscape thinking.

Asciano preserves its historic center in the ancient medieval structure. It's located in the heart of Crete Senesi, close to Desert Accona.
Its origin follows the myth of Romulus and Remus: the legend told that the sons of Remus, Senio and Aschio fled from Rome to escape hatred uncle founder of Rome Romulus, Senio refuging on the banks of Tressa river and creating Siena, and Aschio on the banks of Ombrone river founding Asciano.
In reality Asciano was founded under Siena control to which it remained always faithful, like in the Montaperti historic battle in 1260, when thanks to Asciano, Siena won against Florence.
Merged first with Medici's possession and later to the Grand Duchy of Tuscany, it followed the events of the other Tuscan territories.
Places of interest to visit in Asciano are: the Collegiate Church of St. Agatha, the Etruscan Museum, the San Lorenzo church, the Museum of Sacred Art (with works by Lorenzetti "San Michele Arcangelo" and "Madonna col Bambino").

The Abbey Monte Oliveto Maggiore was founded in 1313 by Bernardo Tolomei and played an important role during the Renaissance not only as a religious center but also as a place of economic and cultural exchange.
Today, it is still an active religious center run by the Benedictines, and it collects inside, valuable manuscripts and pergo restored by monks. It's the seat of the "Istituto di restauro del libro" (Book Restoration Institute).
On the road that leads to the Abbey you will find tall cypresses that, standing in the desert of the Crete Senesi, create a spectacular landscape.
Montaperti is renowned for the famous battle of 1260 between Florence and Siena, won by the latter, to which a memorial pyramid is dedicated. The battle is mentioned by Dante in the tenth chapter of the Divine Comedy's "Hell".

Buonconvento is a historical village that lies in the Ombrone valley. Its history is linked to the history of Siena until the fall of the latter and the annexation to the Medici Grand Duchy in 1554. It keeps intact the fourteenth century walls, as well as some features of the medieval village, as the "chiasso buio" (literally blind alley), a road paved with medieval arches tunnel.
Attractions are the Palace Podestarile with the 25 arms of the old mayors, the Town Hall and Taja Palace, Palazzo Borghese, Palazzo del Glorione, the Oratory of St. Sebastian and the Church of SS. Peter and Paul, the Sacred Art Museum of the Val d'Arbia housed in a 18th century Palazzo Ricci-Socini (which preserves important works, including those of Duccio di Boninsegna).

The ancient village Monteroni d'Arbian on the border of the Crete Senesi, was founded in the 13th century, and it was, until 1810, a Podestà of Buonconvento property. It has grown around the Hospital of Santa Maria della Scala that built a fortified mill in '300 .
During the war between Florence and Siena, the village was attacked and, consequently, annexed to the Grand Duchy of Florence.
The name was inspired by nearby Mount "Roni", while Arbia is the torrent that flows through the town.

Rapolano Terme is located between Val di Chiana and Chianti and is famous for its spa waters of the San Giovanni and Ancient Queriolaia Baths. The thermal waters have been known since antiquity, as testified by the ruins of an Imperial Roman bath complex, and are famous for having hosted Giuseppe Garibaldi, who took refuge there to heal the wound in the Battle of Aspromonte.
The structure of the country is affected by the quarries of travertine and marble, which one time helped to increase local economy.
Rapolano waters, which have a temperature of about 39 ° C (37,4F), are sulphurous-bicarbonate-calcium waters.

San Giovanni d'Asso, inhabited since ancient times, completely surrounds the castle of San Giovanni and is crossed by the River Asso.
The origin of the village dates back to Etruscans, while the development of the city, like testified by the buildings style, was in the Middle Ages.
In the castle of St. John, the highest point of the country, the Museum of truffle was created .
Attractions in San Giovanni d'Asso are the Castle of St John, Castle Montisi (on Monte Ghisi), the castles Accarigi and Castelverdelli, the Parish of St. John the Baptist, the Church of San Pietro in Villore.
The main event is the carousel of Simon in August, when four horsemen (one for every districts of Montisi) try to hit a target with a spear, the festival of crackles on the first Sunday after Easter.