The Abbey of Sant'Antimo, one of the most beautiful Romanesque churches in Italy, is located only 9 km from Montalcino.
According to tradition, in 781 Charlemagne was returning from Rome along the Via Francigena. While camped near Monte Amiata, many in his court and army were struck down by plague. During the night, an angel appeared to the Emperor in dream and recommended that he pick a particular grass, dry it and then make an infusion with some wine and have it drunk by the soldiers. He did this and the army was cured. The grass is known to this day as "Carolina". In return for an end to this scourge, the Emperor promised to found the abbey.
According to historians, the foundation goes further back, to the Longobards and the Monastery of St. Savior (Salvatoris) at Monte Amiata. It is possible that the Abbey of Sant'Antimo was constructed on the site of a Roman villa and it is known with certainty that in the 4th and 5th centuries the village of Castelnuovo dell'Abate, on the hills nearby, was an important inhabited centre, endowed with a parish.
The monastery of Sant'Antimo was in existence in the year 814, as indicated by a document from one Ludovico the Pious that endows the abbey with gifts and privileges. In the 9th century, the abbey faced financial difficulty, to the point that in the 877 Charles II, "the Bald", entrusted it to the Bishop of Arezzo, with the obligation to maintain 40 monks there at his own expense. From the 10th century, the abbot of the monastery was also the Count Palatino, a public position of great importance conferred by the Emperor.
In 992, according to a deed emanating from Pope John XV (985-996), the monastery passed into the direct jurisdiction of the Apostolic See. The year 1118 saw the beginning of the golden years of Sant'Antimo. Count Bernard degli Ardengheschi surrendered his entire patrimony in goods and property, including the Abbey, "in toto I reign Italic et in tota Tuscie marks" to Hildebrand, son of Rustic. A testimony to this exceptional donation was engraved on the steps of the altar as a perpetual memorial of the event. The Abbot Guidone (1108-1128), who received the donation, immediately initiated the great era of the construction of the new church, the Abbey of Sant'Antimo. The apse of the original 9th century abbey still stands alongside, and is dwarfed by, the new 12th century apse. The Abbey became the most powerful monastic landowner and foundation in Tuscany, via its imperial connections and gifts from those travelling the nearby Via Francigena, the pilgrims' route to Rome. At its height, the Abbey owned large tracts of eastern Tuscany from Lucca in the north to Orbetello in the south.
The great years lasted up until the fall of Montalcino, on 12th June 1212, to the Siennese who forced the abbey to sign a treaty surrendering a quarter of the territory of Montalcino in Siena. The abbey then began its slow decline. Entrusted to the Guglelmiti by Pope Nicholas IV (1288-1292) in a deed dated 1291, a brief recovery occurred in the period from between 1397 and 1404 up to the suppression of the abbey in 1462 by Pope Pius II "Piccolomini" (1458-1464) who entrusted it to the bishop of the newborn diocese of Montalcino and Pienza, created on 13th August of the same year.
In 1866 the Italian government decreed the general suppression of the religious orders. The monastic community was transferred to Pescia, where it remained up to 1949. It was only in 1961 that it could re-enter in the Abbey of Sant'Antimo, whose ownership has remained nevertheless with the State. After the transfer of the abbey to the ownership of the new Italian state in 1867, a long period of physical restoration began that ultimately saved the whole building. The restoration was initiated in 1872 and finished in 1895, bringing the church to its current appearance. In 1992 religious activity was reinitiated thanks to the arrival of the Regular Canons Premonstratensi.
No description or pictures can do more that provide a pale reflection of charm of this place. The façade, which remains incomplete, houses a portal, probably one of a pair planned originally, surmounted by a lintel datable to the first half the 12th century, together with capitals, friezes and ferrules. The element that confers a French imprint on this church more than any other is the basilical ground plan, an ambulatory with radial chapels, unique in Tuscany and among the few present in Italy. In the morning, the sun plays on the ambulatory stonework which is the most precious among all those used for the church: alabaster plus travertine from which the capitals and columns are carved. The impact of the light streaming in is accentuated by the nave floor which slopes slightly upwards towards the focus of the dramatic 13th century Crucifix standing behind the altar.
The church is long at 44 m, and is guarded at the entry by two stylised lions, probably destined for the external portal, datable to the 12th century and attributed to the Master of Cabestany, as is the splendid capital with the scenes of "Daniel in the lions' den." The refined geometrical and leaf motifs, precise in outline and cleanly carved, indicate an origin in Auvergne.
Other capitals located in the ambulatory exhibit a Lombard character suggesting that Sant'Antimo was the work of two masters, or a Lombard who had worked in Auvergne.
To the right of the larger church, set at the beginning of the ambulatory, there is a Carolingian chapel of the 8th or 9th century, a small building with a single rectangular aisle and a semicircular apse. Outside on the left, the imposing bell tower rise to around 30 m, divided into four orders, decorated in Lombard style with a with a hint of Pisan taste in the columns at the angles of the base. The bell tower houses two bells, one of which is engraved with Abbot Ugo's name (1216-1222) and the date 1219.

Einst eines der mächtigsten Klöster des Mittelalters, liegt Sant‘Antimo heute einsam in einem Tal, 10 km südlich von Montalcino, inmitten von Feldern und Olivenhainen. Der Campanile (Glockenturm) wird flankiert von einer großen Zypresse, und Ölbäume umgeben die Apsis. Von der Abtei ist nichts mehr zu sehen, aber die erhaltene Kirche ist unbestritten die schönste romanische Landkirche der Toscana.
Als Gründer von S. Antimo an der mittelalterlichen Pilgerstraße gilt Karl der Große. Urkunden belegen, daß das Kloster 813 bereits bestand und mit ungewöhnlich reichen Schenkungen bedacht wurde, die aus ihm schnell eine der reichsten und mächtigsten Abteien des Landes machten.
Vieles spricht dafür, daß es der Bau der Kirche war, der den Niedergang der Benediktiner-Abtei förderte, überstiegen doch die 1118 begonnenen Arbeiten selbst die Finanzen eines so reichen Klosters; 1260 wurden die Bauarbeiten unvollendet eingestellt.
Die Fassade ist schlicht und nur mit wenigen Schmuckelementen versehen.
Rechts schließt sich an die Kirche eine kleine, schlichte, hochmittelalterliche Kapelle an, die sogenannte karolingische Kapelle, ein rechteckiges Schiff mit halbrunder Apsis und ist heute als Sakristei genutzt. Sie unterscheidet sich durch ihre unregelmäßig gesetzten, roh behauenen Quadern eindeutig von den glatten Steinen der Kirche des 12. Jahrhunderts. Unter ihr liegt eine Krypta, die die älteste der Toscana sein soll.
Das dreischiffige Innere ist ungewöhnlich hoch, hat die typische romanische Basilikaform mit Empore und Säulen und Kreuzpfeilern im Wechsel, hat aber eine unglaubliche Leichtigkeit, zumal dann, wenn die Sonne durch die kleinen Fenster kommt und die Alabaster-Säulen und –Kapitelle hell und licht erscheinen.
Den Kapitellen sollte man besondere Aufmerksamkeit schenken - sie sind außerordentlich sorgfältig ausgeführt, vermutlich französisch beeinflußt und haben wunderschöne Motive; das Glanzstück ist „Daniel in der Löwengrube".
Die Emporen haben einen Durchgang zum Chorumgang bzw. einen Verbindungsgang auf der Fassadeninnenwand. Einen Teil der Empore nimmt eine Bischofswohnung ein, die im 15. Jh. eingerichtet wurde; ein Kamin ist noch zu sehen und an den Wänden Freskenreste mit Szenen aus dem ländlichen Leben.
Es war die Wohnung eines Bischofs von Montalcino, der weltlicher Abt von Sant‘Antimo wurde.
Auf den Altarstufen steht eine Art steinerner Chronik, die besagt, daß im Jahre 1118 mit den Bauarbeiten begonnen wurde.
Zur Ausstattung gehören noch ein romanisches Holzkreuz und eine romanische Holzplastik „Madonna mit Kind".
Rechts führt eine Treppe in die Krypta mit einem römischen Grabstein als Altar.
1462 wurde der Konvent aufgehoben, aber seit 1979 lebt hier wieder eine kleine Gemeinschaft von Augustiner-Mönchen.