Overview
Discover Castellina in Chianti: Private Tours, Experiences & Custom Travel
- Fonterutoli - This town, which takes its name from the Latin fons rutilus (clear spring), lies on the road leading from Castellina to Siena. The ancient castle stands on a hill overlooking the Elsa valley, on the border between the municipalities of Siena and Florence and the dioceses of Siena and Fiesole. Reference to it is made in a diploma by Pope Alexander III in 1177. The church, dedicated to San Miniato, was the site of important agreements between Siena and Florence, such as the one signed on 29 March 1201 that granted Siena the right to annex Montalcino and the one signed on 6th October 1208 whereby Siena renounced its right to Poggibonsi and all its territory. Unfortunately very little is left of the original church and the castle=
- Conio - boasts an ancient Romanesque parish church, San Leonino, with a quite beautiful interior and charming, but small cloister. The adjacent buildings once served as residences for the priest.
- Sant’Agnese - another old parish church of Sant’Agnese with its imposing campanile (bell tower), on the main road from Castellina in Chianti to Poggibonsi.
- Cispiano - Here there are imposing ruins of Monternano castle, whose origins date to 1089 AD. The castle was destroyed in 1254 by Florentine troops and the ruins are covered with wild vegetation though one can find doors, arches, walls and underground passages in the midst of the green chaos.
- Rencine - overlooking the fortress of Monteriggioni in the southern part of the area. Here you can find the ruins of another immense but almost completely destroyed castle. The church of San Michele, however, stands in a state of good repair.
Castellina in Chianti in pictures
Gallery
A few frames from our own trips. The rest are in the gallery below.
Map
Get your bearings before you go
Private & Small Group Tours in Castellina in Chianti
Days out with people who know the way
Photo Gallery
Explore Towns and Cities in Chianti
Every town here has its own personality. We know them by name.
Our Featured Properties
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Popular Transfer Routes in Castellina in Chianti
The rides our guests ask for most, with a driver who knows the way.
Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Castellina in Chianti and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.
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