Situated in the heart of the historical center of Castellina in Chianti, one can find the 15th century Palazzo Ugolini, formerly Palazzo Squarcialupi.
The Palazzo has a wide façade with three ashlar doors overlaid with grey sandstone, and eight arched windows on the first floor in line with the square windows of the floor above. The façade bears two stone coats-of-arms belonging to the Ugolini family. The adjacent Palazzo Biancardi has three storeys and two tiers of windows with sandstone frames. Above the entrance is the Medici coat-of-arms of Pope Leo X (Giovanni de Medici, son of Lorenzo the Magnificent and pope from 1513 to 1521) who stayed here when passing through in 1513.
In the past, the Palazzo Squarcialupi was a noble residence with agricultural activity and has recently been restored to become a hotel. Underneath the hotel, in the ancient vaults with its suggestive stone structures, are the antique wine-cellars.

The Etruscan Tumulus of Montecalvario, so called by a small chapel, the last station of the Via Crucis, built on the summit, is a structure of a circular diameter of about 53 meters, made up of four tombs.
The tumulus dating from the seventh-sixth century BC represents one of the most interesting archaeological discoveries all over the Chianti. Built for an Etruscan aristocratic family, the tomb is especially interesting for the town-planning structure of the plan. In the tomb, steel and bronze decorations from a war chariot and a lion's head made of pietra serena were found.

The Tumulus of Montecalvario is located just outside of the village along the road 222.The objects found in the Tumulus of Montecalvario, are exposed in the Archaeological Museum of Chianti Senese di Castellina in Chianti. Near the village of Fonterutoli is the Necropolis of Poggino with other Etruscan tombs.

Fonterutoli was already known in Etruscan times and takes its name from the Latin fons rutolae or fons rutilant (clear spring). It was known as a halting place for food and rest on the road leading from Sienna via Castellina to Florence.
Fonterutoli is a charming village, well worth a visit, and the Etruscan necropolis of Poggino is located in the nearby woods.

Although very little is left of the original church and the castle, a fine villa, referred to as the Castello di Fonterutoli is located beside the piazza in front of the present church, and has been in the family Marchesi Mazzei since 1435.

San Leonino in Conio is a very old parish church that once had control of Castellina in Chianti. Now all that remains is the old Romanesque church, with an interesting interior, a beautiful apse and a small cloistered courtyard.

San Donato in Poggio is a mediaeval fortified village locatedon a hill (Poggio), from which it takes part of its name.
In the past, the urban centre of S.Donato in Poggio was one of the principal fortified settlements of the zone. Today, only part of the fortified walls remain, including the two main gates (Porta Fiorentina and Porta Senese), the bell tower (the Campanone), the watchtower overlooking the valley (the Torrino) and a number of buildings that have preserved the original mediaeval structure of their towers, portals and arches, all constructed mostly of alberese stone.
The town, founded in Roman times, was the principal fortification of the area, serving to defend the Roman road that led from Florence to Siena. The “castrum” (militaary fortress), which in the year 1033 belonged to the family of Count Guidi, became autonomous during the era of the communes. Lying between the cities of Florence and Siena, who were eternally vying for supremacy over the territory, San Donato was frequently the scene of important events, such as the gathering of the Florentine army in 1260, prior to the Battle of Montaperti against the Republic of Siena. The town was destroyed in 1289 by the Ghibellines of Arezzo and subsequently rebuilt with a typical protective wall encircling it.
Portions of the outer wall surrounding the original town are still standing. Of particular interest are the Florentine Gate and the Sienese Gate, each with a scarp tower, as well as numerous turrets, including a bell tower and the so-called “little tower” which overlooks the valley. Within the oldest section of the inner town one can still admire the urban structure of the medieval burg, with narrow streets winding up and down among the thirteenth-century dwellings. Also in this central core of the town are the main town square (Piazza Malaspina), the public cistern, Palazzo Pretorio and the Romanesque church of Santa Maria della Neve.

In the XII century, the S.Donato in Poggio castle enjoyed a certain degree of autonomy and became a free council. In 1218, the castle was definitively subordinated to the Republic of Florence, thereby taking on a considerable strategic importance due to its position on the most direct route of the Strada Romana, the one that linked Florence with Siena. The Florentines and the Siennese concluded a peace treaty at S.Donato in 1255 and the Florentine army assembled in this castle prior to the battle of Montaperti in which they fought the Siennese

The magistrature, situated in the town square, now known as Piazza Malaspina, was decorated with a XV century fresco, which may still be viewed. The building was reconstructed in large part after damage suffered during the last war.
On the other side of the square were the public cistern, which was rebuilt in 1867, and the castle church dating from the XIV century. The late Renaissance facade of the Ticci Palace (which later passed over to the Malaspina family) united the houses and stores to the north and west of the square. Once owned by the noble Ticci and Malaspina families, since the nineteenth century it has belonged to the Pellizzari family. In the village outside the castle, there was a hospital for the poor run by the Augustinian monks, and subsequently run by the St. Maria della Neve confraternity.

Around the year 1000, the Pieve di San Donato was constructed outside the walls of the castle. This church is one of the most typical examples of the Florentine Romanesque architecture. It has three aisles terminating in three semi-circular apses, that envelop the pre-existing bell tower. The façade is constructed of squared albarese filaretto, and inside there is a baptismal font in glazed terracotta by Giovanni Della Robbia (1513), a crucifix attributed to Taddeo Gaddi (1300 - 1366, a disciple of Giotto for 24 years).