The street that leads to Montalcino will allow for an appreciation of the true beauty of the place. Having arrived at the summit the eyes can behold the splendour of an ample and varied panorama from the Senese hills to the mountains of Amiata.

The fortress (constructed to defend the territory in 1361 by the Senese Mino Foresi and Domenico di Feo utilizing the already pre-existing thirteenth-century wall) rises to the highest point of the city and dominates the surrounding valleys.

On the wall of one of the center rooms hangs a Standard attributed to the Sodoma school. The center of this small town is exemplary of the architecture of the late Middle Ages. Following the road across from the fortress you will find on via Ricasoli a gothic marble portal and a rose window that beautify the simple basic Romanesque facade of the Church of Sant'Agostino (thirteenth-century). Nearby, although it will soon be moved to the convent of the church of Sant' Agostino, you will find the Musei Riuniti (civico and Diocesano).

The museums contain pieces of outstanding art work such as a Wooden Cross painted in the twelfth of thirteenth-centuries by an unknown artist. It is one of the oldest Senese works. There are also an Angelo annunciate and a Madonna annunciata, two beautiful wooden sculptures from the early fifteenth- century, as well as a Saint Sebastian and a Madonna with Saints done in Robbian terracotta.

The Duomo (San Salvatore) can be reached by going to the right after leaving the museum. The Senese architect Agostino Fantastici Planned a project (1812-32) to restructure to pre-existing church into the neo-classical norm which dominated the time. Proceed downhill to arrive at the Piazza del Popolo where the Palazzo Comunale (or dei Priori) stands.

In the square is La Loggia which was constructed in the fourteenth and fifteenth centuries. In The contrada of Castelvecchio, is the Church of San Francesco (XIII century) wich as been redone over the course of time. Inside are the frescoes by Vincenzo Tamagni painted in the early sixteenth-century. Just a few kilometers from Montalcino rises the Abbazia di Sant'Antimo (1118).

This is one of the most beautiful Romanseque monastic churches in existence. Its Romanesque-Lombard style gives its structure both a physical force and delicacy at the same time.

The oldest document that mentions Montalcino is dated 715 A.C. It is signed by the Longobard King Liutprando. This document reports a dispute between the Bishop of Arezzo and the Bishop of Siena regarding the possession of some Parish churches in Montalcino. Yet another old document, dated 814, indicates the donation of territory of Montalcino from Ludovico il Pio to Abbazia of Sant’Antimo, a wonderful example of architecture, only 9 Km from Montalcino.

According to the legend, the Abbey was founded in an ancient votive chapel erected by Charlemagne in 781 and was later rebuilt between 1000 and 1118. This extraordinary example of Romanesque Lombard-French architecture made in onyx and alabaster reveals its exceptional in its apse externally formed by radial chapels along an internalambulatory and ist capitals ornamented whith geometrical floral motifs and animals figures: the representation of Daniele in the Lion den, recently attributed to the Master of Cabestany, stands out.

 
Named a City, then diocese in 1462 by Pope Pio II Piccolomini, Montalcino sustained historical moments of great tension due to the dispute between Frorence and Siena and over the dominance of territory. After Siena's surrender to the Medici family in 1555, exiled Siennese sought shelter in the power fortress of the town and founded the Republic of Siena in Montalcino which rule until 1559. From that time on, Montalcino would be subject to the rule of the grand Duchy of Tuscany.

Touring the city, it is possible to admire many medieval structures beginning with surrounding Wall with its gates and remains of some its towers, the City Hall (XIII century), the Porticos of Piazza del Popolo (with its arches from the XIV and XV century); the Cathedral in neo-classic style (built on a parish Church of the XI century); the Sanctuary of the Madonna del Soccorso (erected in the XVII century on the site of a XV century church); Saint Egidio (also know as the Siennese Church, built in the XIV century); and the wonderful churches from 1300s, Saint Agostino (with frescos of the Siennese school of the XIV century) and Saint Francesco (whit the annex of Monastery which open to beautiful cloisters). This church still holds frescos from the 1500s by Vincenzo Tamagni the same artist responsible for the frescos in the old Studiolo,  locaded in the complex of Spedale di Santa Maria della Croce (XIII century), presentily home of the City Hall.

Within the ancient rooms of S. Agostino’s monastery is situated the Museum of Montalcino, one of the most important collections of archeological, medieval and modern art in the district of Siena. The collection offers an almost complete view of this important Tuscan town’s artistic production.

A fixed date in the life of Montalcino is the Festival of the Thrush which is celebrated on the last Sunday of October. The four Quarters of Montalcino – Borghetto, Pianello, Ruga and Travaglio – challenge each others in an archery competition that recall hunting wild boar in medieval times, while a long parede with magnificent costumes crosses the streets of the town accompanied by the traditional music and dance of the folk group Il Trescone.