THE 7 BEST MEDIEVAL VILLAGES IN TUSCANY
June 19, 2024
The medieval villages in Tuscany are little jewels of our Italy! Here is our list of the 7 best villages in Tuscany that you absolutely must visit!
Here is our itinerary to set out to discover Chianti and Tuscany in 3 days: from castles to wineries, from medieval villages to vineyards!
The Chianti area of Tuscany is a real treat for the senses. Imagine rolling hills covered in vineyards, long avenues lined with cypress trees leading to ancient stone farmhouses with red roofs. It’s a magical landscape.
A trip to this area of Italy, which is famous for its wine and food, is an amazing experience. You can do tastings in historic wineries and stroll through the alleys of Chianti’s ancient villages.
Here is our 3-day itinerary to discover Chianti and Tuscany!
Chianti is one of the most famous areas of Tuscany thanks to its vineyard-covered hills, on which paths lined with cypress trees climb, and its wineries, where you can taste wines of the highest quality, and its beautiful stone villages, such as Castellina in Chianti.
The Chianti area stretches across the central part of Tuscany and includes mainly the provinces of Siena, Florence and Arezzo, but has also spread to others, such as Pistoia and Pisa. Chianti has very ancient origins, namely dating back to the Etruscans, who first began the cultivation of vines.
In this area of Tuscany, the wine that dominates is Chianti classico, which you will be able to taste everywhere: from wineries to castles, but also in small village bars.
Visiting Chianti is an immersion in Italian history and food and wine culture, and in this article we offer you our 3-day itinerary in Chianti, discovering one of the most beautiful areas of our beloved Italy!
We followed this itinerary in the summer, taking advantage of a time when tourists prefer seaside resorts, thus giving us space and freedom to move around quietly.
Of course, the best times to visit Chianti are the intermediate seasons, such as spring and autumn. In fact, in spring you can take advantage of good weather and long days, while in autumn the Chianti landscape is at its best, with the vineyards turning red.
We decided to stay in a typical Tuscan farmhouse in the middle of the hills, conveniently enough to reach all the villages on our itinerary in no more than an hour’s drive.
Want more info on the medieval villages in Chianti that you absolutely must visit? 👉 Here is our article!
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On the first day of our 3-day itinerary in Chianti, we started by visiting one of the most famous places in Tuscany: San Gimignano.
This charming village, famous throughout the world, is one of the busiest sites in Italy. In fact, to avoid the high influx of tourists during the central hours of the day, we recommend visiting it early in the morning, late in the afternoon or, even better, in the evening, enjoying a delicious Tuscan dinner!
San Gimignano’s origins go back to ancient times: in fact, traces of Etruscan and Roman settlements can be found here. Instead, the development of its historic center, as we see it now, dates back to the Middle Ages, when this town was located right along the Via Francigena and was a crucial transit hub for pilgrims and wayfarers.
Arriving by car along the Chianti roads, you can see the village of San Gimignano and its towers from afar. In fact, the shape is unmistakable: it sits on high ground overlooking a valley covered with vineyards and olive groves.
There are several parking lots around the village where you can leave your car and then begin your ascent to the historic center of San Gimignano.
In the historic center of San Gimignano you can walk around its 13 towers (few compared to the original, which is thought to have been more than 70) and visit its most beautiful squares, such as Piazza della Cisterna, Piazza del Duomo and Piazza delle Erbe.
We recommend exploring every corner of the town, starting from the Porta San Giovanni and ending at the Porta San Matteo. Visit the alleys where there are many stores selling local products (you cannot miss tasting a good sandwich with finocchiona or, why not, a tasting of crostini and local olive oil!). Finally, you can continue along the walls of San Gimignano.
Another typical product at km 0 that we recommend you to taste is Vernaccia di San Gimignano, a white wine produced particularly in this place and that you can easily find in any wine shop, restaurant or winery in the village.
The towers in the historical center of San Gimignano
Once we had finished our visit to San Gimignano, we headed to Siena, a must-see place that absolutely belongs on the list of things to see in Chianti in Italy.
The city of Siena is world-famous for its famous Piazza del Campo, a semicircular square where the most famous palio in Italy is held every year. Just like San Gimignano, Siena has roots dating back to Roman times, but the most important development of the city took place during the Middle Ages.
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 and main streets of the historic centre, such as Via dei Termini, Via Banchi di Sotto and Via Banchi di Sopra.
All these streets will slowly lead you to the famous Piazza del Campo, where you will find the famous Torre del Mangia and the Palazzo Pubblico where the Comune di Siena is located.
We were fortunate enough to visit Siena when preparations for the Palio were being made and temporary grandstands (still made of wood) were being set up around the perimeter of the square, with a long corridor running underneath to leave space for the entrances to the square. From Piazza del Campo, we advise you to head for the Duomo di Siena, which overlooks the piazza of the same name, and plan a visit inside this marvellous building.
On the second day of our ‘3-day Chianti Tuscany Travel itinerary’ focused on exploring Chianti villages, we began our tour in Castellina in Chianti. This charming village is situated in the southern part of the Chianti valley. The town’s historic centre is a pedestrian-only area that runs along the main street, Via Trento e Trieste, and leads up to the church of San Salvatore. From there, some picturesque alleys wind their way through the town.
If you arrive in Castellina in Chianti by car via the panoramic roads of Chianti, you will need to park your car along the regional road SR222. This road runs alongside the historic center of the town and leads to the main car park, which is about a 5-minute walk from the center.
We recommend walking along Via Trento e Trieste, which is lined with shops selling local gastronomic products, until you reach the church of San Salvatore. From there, continue to Piazza del Comune, which is overlooked by the Rocca di Castellina in Chianti. This building, made entirely of stone and now serving as the municipality’s seat, is an ancient fortress dating back to the 11th century and currently houses the Archaeological Museum of Chianti Senese. The Fortress was one of the first buildings constructed to defend the town centre, along with the city walls. Today, parts of the walls still surround the historic centre. Continue your walk from Piazza del Comune up to Viale IV Novembre for an enchanting view of the Chianti hills. This is also where the weekly market is held, featuring stalls full of typical gastronomic products from the area.
Via delle Volte is one of the most evocative alleys in Castellina in Chianti. It is an almost entirely covered street that passes under the stone vaults on which the houses of the historic center rest. It runs parallel to Via Ferruccio, where various shops and the Tourist Information Office are located.
Following our visit to Castellina in Chianti, we continued along the Chianti roads to our first winery appointment at Castello di Verrazzano, near the village of Greve in Chianti, for an exceptional wine tasting experience. Exploring the wines offered by the wineries in this region is a must-have experience for anyone looking to fully experience Chianti.
Castello di Verrazzano has ancient origins. It was built during the Middle Ages on the remains of Etruscan and Roman settlements. Today, it has an estate covering more than 200 hectares.
The landscape surrounding Castello di Verrazzano is incredible, with vast expanses of vineyards as far as the eye can see at the foot of the ancient residence. From its panoramic terrace, one can admire the Chianti hills. This historic winery is among the most beautiful in the Chianti region. We highly recommend booking a visit and a guided wine-tasting to sample the Chianti Classico wines on offer. The Riserva and Gran Selección are two outstanding wines.
You can also enjoy a quick lunch of mixed Tuscan crostini on the restaurant’s panoramic terrace, which is a truly fantastic experience!
From Castello di Verrazzano, we went to another nearby mansion, Castello Vicchiomaggio. This mansion is located on a hilltop, surrounded by vineyards that stretch as far as the eye can see. It is possible to stay overnight or enjoy an excellent lunch in the restaurant, which serves typical local cuisine. The wine cellar at Castello di Vicchiomaggio offers a good selection of wines, from whites to reds, including Chianti Classico, of course.
We enjoyed a superb white wine tasting in the castle garden, which boasts terraces with stunning views of the surrounding vineyards and hills.
After the tasting, we resumed our journey along the picturesque Chianti roads towards the town of Greve in Chianti. Located in the hills along the regional road SR222, the same road that passes through Castellina in Chianti, the historic centre of Greve in Chianti is situated along the main street, Via Roma. Car parks are available near the historic centre along the regional road, allowing for easy access to the centre with a short walk. We suggest walking along Via Roma, which is lined with small, typical Tuscan houses, shops, and wine bars, until you reach the main square of Greve in Chianti, Piazza Giacomo Matteotti.
The square is entirely surrounded by porticoes, under which there are many shops selling typical local products, such as wine shops and butchers, and also restaurants with lovely outdoor areas.
The second day of our 3-day Chianti and Tuscany itinerary was dedicated to villages and castles, starting our tour from Castellina in Chianti.
Castellina in Chianti is a charming village located in the southern part of the Chianti valley.
The historic center consists of a pedestrian area that stretches along the main street, Via Trento e Trieste, all the way to the church of San Salvatore.
If you arrive in Castellina in Chianti by car, driving along the scenic Chianti roads, you will need to park your car along the regional road SR222. In fact, this road skirts the historic center of the town and is flanked by the main parking lot, about a 5-minute walk from the center.
You can walk along Via Trento e Trieste, overlooked by various stores and stores selling local gastronomic products, to the church of San Salvatore. From here you can then continue your walk to the Piazza del Comune, overlooked by the Rocca di Castellina.
This building, made of stone and now the seat of the municipality, is an ancient fortress dating back to the 11th century and houses the Archaeological Museum of the Chianti Senese.
The Rocca was one of the earliest buildings built to defend the town, along with the city walls, which are still present today in part around the historic center.
The second day of our 3-day Chianti itinerary was dedicated to villages and castles, starting our tour from Castellina in Chianti.
Castellina in Chianti is a charming village located in the southern part of the Chianti valley.
The historic center consists of a pedestrian area that stretches along the main street, Via Trento e Trieste, all the way to the church of San Salvatore.
From the Town Hall Square continue to Viale IV Novembre, from which you can enjoy a lovely view of the Chianti hills. The weekly market is also held here, with stalls full of local gastronomic products.
One of the most charming alleys in Castellina is Via delle Volte, a street almost entirely covered by stone vaults on which the houses of the historic center rest and parallel to Via Ferruccio, where you will find various stores and the Tourist Information Office.
After visiting Castellina in Chianti, we set out again along the Chianti roads.
We headed to the first winery where we had booked an appointment for an excellent wine tasting: the Castello di Verrazzano, located near the town of Greve in Chianti.
Discovering the wines that the wineries in this area have to offer is definitely an experience to have if you really want to visit Chianti to the fullest.
Castello di Verrazzano has ancient origins: in fact, it is a mansion built during the Middle Ages on the remains of Etruscan and Roman settlements and which today has an estate of an area of more than 200 hectares.
The landscape surrounding Castello di Verrazzano is incredible, with wide expanses of vineyards as far as the eye can see at the foot of the ancient mansion from whose panoramic terrace the Chianti hills can be admired.
In our opinion, this historic winery is truly one of the most beautiful in Chianti. In fact, we highly recommend that you book a tour and guided tasting so that you can learn about the Chianti Classico wines on offer (the riserva and gran selezione are two resounding wines).
You can also accompany your tasting by a quick lunch of mixed Tuscan crostini sitting on the restaurant’s panoramic terrace-a truly fantastic experience!
Via delle volte in Castellina in Chianti
Chianti wine tasting at Castello di Verrazzano
Wine tasting at Castello Vicchiomaggio
From Verrazzano Castle we headed to another mansion, located nearby: the Vicchiomaggio Castle.
This castle is also located on the top of a hill, surrounded by vineyards that stretch as far as the eye can see. Moreover, here you can stay overnight or enjoy an excellent lunch in the restaurant of typical territorial cuisine.
The wine cellar at Castello di Vicchiomaggio offers a good selection of wines, from whites to reds, including, of course, Chianti Classico.
After visiting the winery, we had an excellent tasting of white wines, served in the castle garden, which has terraces with beautiful views of the surrounding vineyards and hills.
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Once we finished our tasting, we were once again immersed in the panorama of the Chianti roads and headed towards the town of Greve in Chianti.
Greve in Chianti is a town located down in the hills along the regional road SR222, the same road that passes through Castellina in Chianti.
The historic center runs along the main street, Via Roma.
Parking lots are located near the historic center, along the regional road, where you can leave your car, after which you can reach the center with a very short walk.
We recommend walking along Via Roma, lined with small typical Tuscan houses, stores, stores and wine bars, until you reach Greve in Chianti’s main square, Piazza Giacomo Matteotti.
The square is entirely surrounded by arcades, under which there are many stores selling typical local products, such as wine shops and butcher stores, as well as restaurants with lovely outdoor seating.
HERE you can find the ticket for a full day tour of castles and wine tasting
On the third and final day of our itinerary to visit Chianti, we continued our journey to discover the Chianti villages, starting with a visit to Radda in Chianti.
The historic center of Radda in Chianti is smaller in size than the other villages we visited but is equally charming and evocative. Its smaller size also makes it less crowded with tourists, an aspect that is certainly appreciable.
The historic core of Radda in Chianti is almost circular and crossed by the main street, Via Roma, overlooked by stores selling typical products and also various craft stores. Radda in Chianti is truly enchanting, and its historic center is a typical portrait of an ancient Tuscan village.
The town walls are still intact and it is possible to take a pleasant walk with a view of the magnificent panorama that surrounds Radda in Chianti.
HERE you can find the ticket for a wine tasting in Radda, including Chianti Classico
After visiting Radda in Chianti, we headed to Castello di Albola, another winery of excellence in Chianti.
Castello di Albola is a perfectly preserved historic mansion, and its estate covers an area of more than 900 hectares, partly covered by expanses of rows of vines.
More than a castle, one can speak of a real medieval village, in fact it consists of several cottages and the wonderful manor house with its wonderful garden overlooking the valley.
The Albola Castle offers various experiences, including, of course, wine tasting, which can also be accompanied by a visit to the cellars, which are, of course, located in the basement, and to the vineyards, and an excellent lunch based on typical Tuscan products.
The top wine offered by Castello di Albola is of course Chianti Classico, also in the Riserva and Gran Selezione versions (we enjoyed the Santa Caterina very much), but other interesting wines such as Acciaiolo and Vin Santo are also offered, as well as Albola’s extra virgin olive oil.
In addition to wine tasting, we stopped for lunch in the wonderful inner courtyard, where we enjoyed a fantastic Tuscan sausage cooked expressly on the barbecue.
After lunch we headed for our last stop, the village of Panzano in Chianti.
This, too, is one of the Chianti villages of medieval origin, where the city walls have remained largely preserved.
If Radda in Chianti was a small village, Panzano ranks first in terms of small size. In fact, the “historic center” covers a very small area where the Panzano Castle and Church are located. We found it very interesting to take a walk through the alleys around and leading to an area where there are the remains of the village walls from which you can enjoy a beautiful view of the surrounding olive groves.
View of the Tuscany countryside from Panzano in Chianti
Among the vineyards of Castello di Albola
Internal courtyard of Castello di Albola
In this article, we have presented you with our itinerary in Chianti and Tuscany to visit this wonderful area of Italy, and we hope it will provide you with inspiration for planning a trip through these magnificent lands.
The towns and villages of Chianti that are worth a visit are countless, as are the wineries, of Italian companies of excellence that deserve to be discovered and enhanced. Stay connected with us via the newsletter and social channels and as always…trip to try!
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