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The Chianti region is situated at the center of a territory comprised of the cities of Arezzo, Volterra and Fiesole and the borders of the three jurisdictions met near Poggio Firenze, above S. Polo, where an inscription in the Etruscan language has been found attesting to the sacred nature of the spot. After the fall of the Roman Empire there ensued a period of almost total darkness. Wars, famine and barbarian invasions gave rise (not without reason) to the term "the Dark Ages" to describe this period in history. But it was also the period when feudalism and its castles developed and when the first Christians began evangelizing the zone. Subsequently Chianti was host to the settlement of the monastic orders of the Vallombrosans of S. Giovanni Gualberto and Romualdo di Camaldoli and it was these orders which founded the great abbeys that one can admire to this day.
From this point we can begin to talk about Chianti's art history. Situated as it is between two major poles of Italian art and culture, Florence to the north and Siena to the south, it was impossible for this territory not to feel their respective influence. However, certain original contributions are not lacking and can be found in some minor manifestations such as rural and devotional architecture i.e. the typical farmhouse, dry stone walls, and the chapels and votive tabernacles scattered here and there along the dense network of roads which link the various towns. Without ignoring these forms, our emphasis is on some of the more interesting aspects of the art which developed in Chianti, for the most part closely connected to noble residences (castles or villas) or to religious life (the parish church, church or abbey). Starting with the castle, today one can still see the essential lines of the original construction, despite inevitable modifications in the course of centuries. A feudal structure is today still visible in some of the best preserved castles (Montefioralle, Uzzano, Convertoie, Vertine, Meleto, Barbischio) and takes one back to the type of economy which characterized that period in history. The strong walls enclose a self-sufficient agricultural and productive unit. Inside, one can clearly distinguish the highest and most fortified part which was the home of the lord, surrounded by the homes of their servants and workers and the small church. The fields and pasture lands were outside and at night everyone returned to the safety of their homes behind the thick castle walls.
Today, looking at the division of property surrounding these fortified centers one can still reconstruct their history: for example, certain fields or woods have always belonged to the church and constitute the farmland with relative farmhouse of the parish priest… The power of the lords is evidenced by the fact that some ancient and noble families have preserved their property to this day (the Ricasoli at Brolio and the Gherardini at Vignamaggio). The transformation of the castle to a villa/farm in the 1400's changed the external appearance of the buildings as one can observe in the Castle of Uzzano near Greve. Part of the ancient walls ( to the north) are preserved, while the part exposed to the south was adapted to the needs of the new period, more secure and open to economic, artistic and social relations. The austere medieval chisel work is contrasted by the elegant lines of the smooth sandstone and plaster, the loggia's and columns all surrounded by marvelous vast gardens in the Italian style. Many of these castles have become important economic centers for the production and sale of Chianti Classico wine and are open to the public almost on a regular basis.
Up to a few years ago the larger castles were equipped with social structures such as a school, a church and a store and in the interior the network of streets, squares and entry gates still exist. Inside the walls it's interesting to note the still well-tended vegetable gardens and vines which one can imagine once provided the basic necessities of life to the inhabitants in the case of prolonged siege. The urban growth of these castles, almost all of which were situated on hilltops, did not undergo further expansion thanks to the harshness of their location. Expansion occurred subsequently in the valleys with the birth of new centers during the comunal period when commerce picked up and communications were rendered safer and easier.
By the end of the 13th century Florence controlled almost all of the territory of Chianti. Religious architecture developed at an equal pace with civil architecture, since the ecclesiastical hierarchy had by now substituted the civil one after the collapse of the Western Roman Empire. The first news of towns, parish churches and some important places of worship comes through "toponomastia" and it is this science that leads us to the first Christian settlements. The worship of some of the saints who evangelized this area has survived almost intact to modern times: S. Leolino, S. Eufrosino, S. Cresci, to mention only the most significant. Churches and parish churches in layered alberese stone of simple Romanesque layout are dotted throughout the territory between Florence and Siena and despite subsequent modifications they almost all preserve their original structure which is quite simple; the façade "a capanna", the bell tower "a vela", sober interiors with elegant rows of columns in sandstone, with 1 or 3 naves. Some of the loveliest parish churches in the area are S. Leolino in Panzano, S. Maria Novella in Radda, S. Donato in Poggio and S. Pietro in Bossolo in the township of Tavernelle. Two of the 4 abbeys (3 Vallambrosan and 1 Camaldolese) built by the monastic orders which were so important to the evangelization of Chianti have remained in good condition: the one at Passignano which with its superb towers is surely the most important Christian monument in this area in terms of art and history, and that of Coltibuono. The abbey of Montemuro has disappeared, leaving only a town of the same name, while that of Monte Scalari has been privatized and is partially destroyed. Two other elements of the hill landscape deserve a separate paragraph, the farmhouse and the market square.
The farmhouse, in its rustic simplicity and harmony, is the construction which has left the most important mark on the Chianti countryside. The dominant structure consists of a quadrangular building with an external staircase and loggia which overlooks a courtyard (aia) , usually surrounded by a wall against which leans the barn, and not far away is the pigsty. The stall for the other animals is usually located in the main part of the building, along with the cellars underground. On the roof a square appendix similar to a little tower almost always stands out; this is the dovecot. .There are also more complex constructions, inhabited by more than one family, especially in the richer zones where the land is cultivated, or those originating as ancient feudal homes.
The other architectural element which almost everywhere indicates the concrete presence of commercial activity is the square, to be found in any town, large or small. A masterpiece of its kind is that of Greve, surrounded on three sides by portico's in brick which capture the motifs of older ones in wood and straw. It is the most classic example of the marketplace as found in many other centers in Tuscany and beyond. The place-name "Mercatale" (market square) is rather frequent in Chianti and the vicinity; Mercatale Val di Pesa, Mercatale in Valdarno, Mercatale a Radda. Given the commercial development of these towns, the square is harmoniously inserted among its houses where it can accommodate the influx of out-of-towners and residents on established market days.