MONTEPULCIANO (at 6 km) This is the largest Comune in the Sienese Valdichiana and contains six other villages: Abbadia di Montepulciano, Acquaviva, Gracciano, Montepulciano Stazione, S.Albino and Valiano. The poet Agnolo Ambrogini (known as "il Poliziano" from the Latin "mons Politianus") was born here. The town is said to have been founded by the Etruscan king Porsenna and exhibits impressive architecture, mainly but not only Renaissance. Michelozzo, Baldassarre Peruzzi and Vignola all worked here, as did Antonio da Sangallo il Vecchio who designed the temple of San Biagio.
Apart from the wonders of the historical centre of Montepulciano the tourist would do well to visit the spa centre at S.Albino. The local economy is based on agriculture and the town is famous for its Vino Nobile. In th summer the town hosts the "Cantiere Internazionale d'arte" and in the mid-Augut holidays the "Bruscello", a traditional show spoken in rhyme, is performed on the Cathedral steps. On August 29 a wine barrel race, the "Bravìo", is run between the different contrade, or districts, of the town and there is a procession in 13th-century dress.

MONTEFOLLONICO (at 9 km) Montefollonico (576m above sea level) is a small medieval village whose raison d'être is found in the past rivalries between the republics of Siena and Florence; in fact the village was born as a Sienese fortress, against the "Florentine" Montepulciano.
The first evidence of the area being inhabited dates as far back the Neanderthal man (approx. 60,000 years ago) with the Lithic tools found in the area of "Il Tondo" (now the public garden).
In the following centuries we have accounts of a territorial dispute in the year 715 for the ownership of the church Pieve di San Valentino. The history of the village as such began in the XIIIth century with the foundation of the church Pieve di S. Leonardo by the Cistercian monks from the monastery nearby, who by dedicating themselves to fulling wool gave the village its name Mons a Fullonica. After various events Montefollonico was incorporated into the Tuscan Grand Duchy in 1555.

PIENZA (at 20 km) The town stands on the top of a hill which overlooks the splendid Val d'Orcia. Enea Silvio Piccolomini was born here in 1405 and when he became pope Pius II in 1458 he decided to transform his modest village into the perfect town, an admirable example of the humanistic period, and entrusted the design to Bernardo Rossellino. Piazza Pio II is intact, incorporanting the most rigorous of Renaissance perspective, and containing the cathedral and Palazzo Piccolomini. The town's main axis is corso Rossellino, lined with houses built by the nobility in the 14th century. Pienza is a mainly agricultural centre, particularly famous for its pecorino cheese. The traditional cheese show, "fiera del cacio" takes place on the first Sunday in September. The flower show "Pienza e i fiori" takes place in mid May. Also to be visited is Monticchiello, made famous by its "Teatro povero", a new play anacted each summer by the local inhabitants.

MONTALCINO (at 45 km) Without doubt, Montalcino lives a life of many souls. Montalcino as the birthplace of Brunello wine, whic someone once defined as the best and most renowned wine in Italy. From the height of its 564 m. the ancient town dominates the surrounding countryside, clinging to the slopes of a hill crowned by the imposing 14th-century fortress. In the labyrinth of little streets, amongst artisans'shops, small cafès and places selling typical local produce ( besides the wine, their honey and locally-made biscuits called "dead bones" are also well-known) the sights worth seeing are the fine Town Hall, the Bishp's Palace ( housing the United Civic, Diocesan and Archaeological Museums, with works by important 13th-16th century Sienese artists, such as Bartolo di Fredi, Il Sodoma, Bartolomeo Neroni), the antique Crucifix of Saint Antimus dating back to the mid-12th century, and the churches of Saint Augustine, Saint Giles and Saint Francis, all built between the 13th and 14th centuries, as well as the Sanctuary of our Lady of Succour. But it is just a little way out of town, near Castelnuovo dell'Abate in the Starcia valley that thhe heart of Montalcino spirituality is to be found:the Romanesque abbey of St.Antimus, a striking little temple enveloped in an almost magical atmosphere, founded by Charlemagne in 781. Finally, there are several castles on Montalcino land: the one worthy of mention is Poggio alle Mura, which has Longobard origins.

CORTONA (at 24 km) One of the twelve cities of the Etruscan League-substantial fragments of its primitive cyclopean defences can still be seen, incorporated in the medieval walls. Apart from a few fine Renaissance palaces, the prevailing character of Cortona's architecture is medieval, conferring on the steep narrow streets a strong sense of atmosphere. The city is commandingly situated (altitude 600 metres) and there are magnificent panoramas to every point of the compass, embracing the whole of the Val di Chiana.
Prominent among many art works of various periods in the Museo dell'Accademia Etrusca are the Etruscan Chandelier known as the "lamp of Cortona", one of the most celebrated bronzes of antiquity, and the "Polyhymnia Muse", an encaustic painting of the Roman era, of Remarkable beauty. The Museo Diocesano displays works by Luca Signorelli, distinguished Renaissance painter and native of Cortona, and a much-admired "Annunciation" by Beato Angelico.
The most important medieval buildings are the churches of San Francesco and San Domenico and The Palazzo Casali, which has a renaissance facade. In these, and in the Renaissance churces of Santa Maria Nuova and San Niccolò, valuable works of art are preserved.
The neighbourhood of Cortona is dotted with Etruscan monuments: the tomb called "Tanella di Pitagora" (2nd century B.C.) in the Cannaia district; Etruscan tombs and a hypogeum (6th and 7th centuries B.C.) in the Sodo district. Among the evocative holy places are the romanesque church of Sant'Angelo in the Metelliano district, the beautiful church of Santa Maria delle Grazie (16th century) at Calcinaio and the Convento delle Celle, founded by San Francesco d'Assisi. Severini's "Via Crucis" (20th century) accompanies the mystic ascent linking the inhabited centre with the sanctuary of Santa Margherita which towers above the town and which, in its turn, is overshadowed by the powerful defences of the Girifalco fortress.

SAN QUIRICO (Bagno Vignoni) (at 30 km) Originally an Etruscan town, it acquired importance thanks to the neighbouring Via Franchigena. Federico Barbarossa, in 1154, received the ambassador of Pope Adrian IV here and this event is recalled in the "Festa del Barbarossa", 3° Sunday of June. In 1167 it was seat of the Imperial Vicar. The Florence of Cosimo I de' Medici purchased it in 1559.
The Collegiata of SS. Quirico and Giuditta is in the Romanesque style: it has three portals and one whit faces southern is attributed toGiovanni Pisano. Inside is found the polyptych of Sano di Pietro and a Chorus from 1432-1502. Palazzo Chigi is from the XVII century. The "Horti Leonini"(16 th century) are one of the first examplesof of Italia Garden style: from August to October there is an exhibition of sculpture "Forms in green". The Romanesque parish church of S. Maria Assunta was, perhaps, constructed on the remains of a pre- Cristian temple. The inside of the church of S. Francesco holds two wooden polychrome statues and a Robbia's Madonna. The area of Bagno Vignoni was known about from roman times through the benefits of the waters from its spring which gush forth at temperatures of more 50°C. and are gathered in the big basin which lies at the centre of the town and gives it its evocative appearance. There is a small sanctuary dedicated to S. Caterina from Siena situated at the side of the basin. The castle of Vignoni looks down upon the town and can be roached either by S. Quirico or by Bagno Vignoni: a natural walk which can be made on foot.