Ultimate Chianti and Tuscany Itinerary: 3 Days of Bliss
March 10, 2024
Here is our 3-day Chianti and Tuscany itinerary, for a full immersion in italian food and wine history and culture!
In Tuscany in the provinces of Siena, Florence and Arezzo, hills covered with vineyards and olive groves alternate with water courses and small medieval villages of red-roofed stone houses.
The medieval villages in Tuscany are little gems of our beloved Italy and in this article we tell you about the ones you absolutely cannot miss! Here is our list of the 7 most beautiful villages in Tuscany you absolutely must visit!
When we think of Tuscany, the first image that comes to mind is of hills covered in vineyards, with winding paths surrounded by tall cypress trees leading to small medieval villages: this is the perfect description of the Chianti Valley, one of the most beautiful places in the Italian hinterland and home to some of the best villages in Tuscany.
The origins of Chianti are ancient, dating back to Etruscan times, when this area was already cultivated and vines were first planted. This vast area is home to some of the most beautiful villages in Tuscany. Visiting medieval villages in Tuscany is like being immersed in the history and origins of not only Italian cuisine, but also our civilisation.
We spent a few days visiting this wonderful area of Tuscany and in this article we offer you our list of 7 medieval villages in Tuscany that you absolutely must not miss!
Castellina in Chianti is certainly one of the most beautiful villages in Tuscany. Its origins date back to Etruscan times.
The historic centre of Castellina is small and consists of a main pedestrian area that stretches from Via Trento e Trieste to Via delle Mura.
If you arrive in Castellina in Chianti by car, we recommend that you park your car along the SR222, which runs parallel to the historic centre of Castellina, where there is a public car park, about a 5-minute walk from the centre.
We suggest you walk along Via Trento e Trieste, a street lined with shops and workshops selling local food products. Continue until you reach the church of San Salvatore and then head towards Piazza del Comune, where you will find the Rocca di Castellina in Chianti. This historic building, built entirely of stone and now the Town Hall, was an ancient fortress dating back to the 11th century and now houses the Chianti Senese Archaeological Museum. The Rocca, together with the town walls, was one of the first defensive structures in the town and part of the walls can still be seen around the historic centre. From Piazza del Comune, continue your walk along Viale IV Novembre, from where you can admire a splendid view of the Chianti hills and visit the weekly market, full of stalls selling local produce.
One of the most interesting alleys in Castellina in Chianti is the Via delle Volte. This route, which is mostly covered, winds under the ancient stone vaults that support the houses in the historic centre. Via delle Volte is parallel to Via Ferruccio, where you will find various shops and the Tourist Information Office.
Castellina in Chianti is undoubtely one of the best Tuscany villages. If you can, go there during the ‘Calici di Stelle’ event, held every year on the night of San Lorenzo. Various Chianti wine cellars will offer tastings of their best wines!
San Gimignano is one of the best medieval villages in Tuscany and is absolutely the most scenic already from the view it offers as you approach by car. This UNESCO-protected village stands on top of a hill, its towers defining its unmistakable profile.
As one of the most beautiful villages in Tuscany, San Gimignano gets pretty crowded with tourists. If you want to avoid the crowds, we recommend visiting in the early hours of the day or in the evening. You can enjoy an excellent dinner of typical Tuscan cuisine and sip an excellent glass of Chianti or Vernaccia di San Gimignano, a wine produced only in this area.
If you want to visit San Gimignano, you’ll have to leave your car in one of the public car parks below the town walls and walk from there.
Like Castellina, this village has origins dating back to Etruscan times and the historic centre dates back to medieval times, when San Gimignano was an important point on the Via Francigena, travelled by wayfarers and pilgrims.
The historical centre of San Gimignano is a succession of squares surrounded by medieval palaces, such as the Piazza del Duomo, the Piazza delle Erba and the Piazza della Cisterna, and of stone towers connected by the narrow network of alleys overlooked by wine shops and workshops. In addition to the historical centre of San Gimignano, we also recommend a walk along the medieval walls, from which you can enjoy a beautiful panorama of the Chianti Valley.
Via delle Volte in Castellina in Chianti
San Gimignano
Castellina in Chianti
Despite its very small size, Radda in Chianti is absolutely one of the most beautiful villages in Chianti you must not miss. The historic centre of this village has a typically medieval architecture with a circular shape enclosed by walls and is crossed by Via Roma, the main street, lined with shops and wine bars. Today, all that remains of the medieval castle are the walls and the defensive stone towers. The village walls are still intact and it is possible to take a pleasant walk with a view of the magnificent panorama surrounding Radda in Chianti.
Given its smaller size, this Tuscan village is less crowded with tourists and is a great place to enjoy some relaxation away from the crowds of tourists.
In the surroundings of Radda in Chianti there are several farms where it is possible to visit, such as the Chianti Museum, taste typical local products and sample some excellent Chianti Classico wine.
Here is our 3-day Chianti and Tuscany itinerary, for a full immersion in italian food and wine history and culture!
Greve in Chianti is one of the best Tuscany villages in the Chianti region situated on flat land surrounded by hills. In medieval times it was close to two important roads, the Via Volterrana and the Via Francigena, which made the village an important trading post. You can reach the village of Greve in Chianti by taking the regional road SR222, the same road that leads to Castellina in Chianti.
The historical centre of Greve in Chianti develops along Via Roma, the main street of the village, which leads to Piazza Giacomo Matteotti. This is the main square of the village, overlooked by porticoes that host various shops selling typical local food and wine products and bars and restaurants with open-air terraces where you can stop for a pleasant break and enjoy a (further) glass of Chianti.
If you have the opportunity to visit this village in September, we would like to point out that the second weekend in September one of the most popular events takes place in Greve in Chianti: the Chianti Classico festival.
Next up is Volterra, another of the most beautiful villages in Tuscany, in the province of Pisa. This one’s a bit bigger than the others medieval villages in Tuscany we’ve already talked about and has lots to see, like the Palazzo dei Priori, the oldest palace in Tuscany, and the Medici Fortress, the Roman theatre and the Etruscan archaeological park Enrico Fiumi, which is right next to the Medici Fortress.
Volterra has a long history, going back to the Etruscan period. It was an important place thanks to the deposits of alabaster underground, which is still a product sold and imported to various countries.
The heart of Volterra’s historic centre is the Piazza dei Priori, which is overlooked by some of the town’s most important buildings, including the Palazzo dei Priori, the Palazzo Pretorio, the Torre del Porcellino and the Palazzo Vescovile. As well as the square, the historic centre of Volterra is worth exploring on foot. It’s lined with medieval buildings housing wine shops and shops selling typical Tuscan food and wine products.
To visit Volterra, you can leave your car in one of the public car parks outside the medieval walls that surround the city and drive up towards the historic centre. The two largest car parks are the underground car park, near the Enrico Fiumi Archaeological Park, and the Vallebona car park, located near the Roman Theatre.
Volterra historical centre
Panzano in Chianti is another of the medieval villages in Tuscany that deserve your visit, although it is very small, even smaller than Radda in Chianti. This village of medieval origin, whose walls are still largely preserved, is built around the Castle and the Church of Panzano. We suggest a stroll through the narrow alleys of this quaint but lovely village, until you reach the remnants of the walls, from which you can take in a gorgeous view of the olive groves and the Chianti Valley.
Although not exactly a village but a real city, we cannot fail to include Siena in this list of the most beautiful villages in Tuscany.
We were lucky enough to visit the historical centre of Siena during the preparations for the famous Palio in its most famous square: the Piazza del Campo. This circular square is completely surrounded by historical wooden grandstands that lean against the buildings facing the square. On the square stands the famous Torre del Mangia and the Palazzo Pubblico, the municipal seat of Siena.
Siena’s origins date back to Roman times, but the historic centre as we see it today is almost entirely medieval. The most important streets in the historic centre of Siena are Via dei Termini, Via Banchi di Sopra and Via Banchi di Sotto, where various shops and shops selling typical products can be found. Another important landmark in the historic centre of Siena is Piazza del Duomo, overlooked by some of the city’s most important buildings, such as the Duomo and the National Archaeological Museum.
The most convenient area in which to find a parking space and then walk to the historic centre of Siena is around the Fortezza Medicea and the stadium. From here you can quickly make your way through the alleys to the city centre.
View of the hills in Panzano in Chianti
Piazza del Duomo di Siena
In this article we have presented you with our list of 7 best medieval villages in Tuscany that you absolutely must visit, but there are many others that are worth a visit, such as Montepulciano and Montalcino! We hope this article has enticed you to set out and discover the medieval villages in Tuscany and this wonderful part of Italy! Stay connected with us via social channels and the newsletter and as always… trip to try!
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