Holiday Villas and Small Hotels in Tuscany

35 Charming Villages in Tuscany!

Dear friends,

First of all, welcome back to the blog!

With today’s article I propose to share an interesting insight to some thirty-five Tuscan villages. Among this selection are the villages, divided by provinces, which I esteem to be of the greatest interest while traveling through Tuscany.

My desire is to help my readers in their search of places of interest, and above all,  the top places to visit during a short period in Tuscany.

I hope that I don’t forget any important villages along the way…and we start with:


1 – Barberino Val d’Elsa (Florence) 
Barberino Val d’Elsa is a beautiful medieval town situated in the Chianti Fiorentino area. The village is surrounded by ancient walls and retains the original elliptical. Barberino Val d’Elsa has two medieval gates and a main road that connects the two entrances of the Porta Romana (which faces South to Rome) and the Porta Fiorentina (which faces North to Florence).

For those who want to deepen their knowledge of this village are welcome to read the following article: BarberinoVal d’Elsa

2 – Certaldo (Florence)  
The famous Tuscan writer “Boccaccio”, author of such works as ‘Decameron’ and ‘Dante’s Life’ was born here in Certaldo!

Certaldo is a great place to enjoy authentic Tuscany, especially during September/ October, during the Festival Boccaccesca, which is a major food and wine festival in the area.

During the month of July there is the interesting popular festival Mercantia.

3 – Vinci (Florence) 
In Vinci, everyone talks of Leonardo: his birth house, the church where he was baptized, the museum and library dedicated to him. As well as the beauty of the landscape, which Leonardo had seen, and which possibly was the true inspiration for the artist.

To learn more about this town you may read the following article: Vinci Where Leonardo was Born

4 – Fiesole (Florence) 
A few km from Florence you will find Fiesole, a little town from where you can appreciate Florence and the hills surrounding the city. Fiesole can easily be reached by car or bus from Florence’s centre. 


5 – Barga (Lucca) 
Barga is a must if you are going to explore northern Tuscany. This medieval town is a real hidden gem because of its location; just off the main tourist route between the hills of Tuscany and the Apennines. Barga with its 410 metres above sea level is a town worth visiting.

Fore further information on Barga, I suggest the following reading: Barga: One of the most Beautiful Villages of Tuscany.

6 – Montecarlo (Lucca) 
The city of Montecarlo is located in the province of Lucca and its territory covers an area of 1,559 hectares and a population of about 4,335 habitants.

The old town is very well preserved and surrounded by beautiful walls. Monte Carlo hill is covered with vineyards and olive groves and boasts a production of olive oil and wines of remarkable quality. 


7 – Volterra (Pisa) 
Surrounded by medieval walls, Volterra dominates from the top of this beautiful part of Tuscany. City of Roman origin, it has conserved its beautiful theater from the year 13 DC. The city has been used as the setting for numerous films, for example in one of the settings from the saga “Twilight”.

Volterra is without a doubt a must to visit. For those who wish to learn more about this place I recommend reading the following article: The city of Volterra

8 – Peccioli (Pisa)
The medieval city of Peccioli is situated in the region Valdera between Pisa and Volterra. The city of medieval design and narrow streets has a beautiful central square where there is the Romanesque church of San Verano. This church houses an important painting of St Nicholas and nineteenth-century bell tower which was built by the architect Bellincioni. Peccioli is found on the ‘Wine Route’ and there are many places visitors can sample locally produced wines. 

9 – Lari Casciana Terme (Pisa) 
The small town of Lari has been inhabited since Etruscan times.

Lari is situated in an area where three peaks join together in the hills of Pisa. The castle looms over the city centre and its construction dates back to medieval times. Most of the current structure is from the mid-seventeenth century. This castle was an important military settlement for the Republic of Pisa because of its dominant position, since its location can be seen from various hills from Pisa to Volterra. From the area that overlooks the coast you can see the village of Peccoli. In this town you can enjoy natural hot springs. 

10 – Casale Marittimo (Pisa) 
On the hill of Poggio al Bruno, with beautiful views of the coastal plains, surrounded by vineyards, olive groves and grain fields Casa Marittimo is a place which has been known since the eighth-century for its old Church of San Andres.

Torn between Casale Vecchio and Casale Nuovo, the city is a fortified medieval town of which still stands are the wall and the two gates. This ancient village is immersed in a wonderful landscape of tinted green near the sea. 

11 – Castelnuovo Val di Cecina (Pisa) 
Located among some of the most beautiful hills of Tuscany Castelnuovo Val di Cecina emerges as a well-preserved medieval village that extends along the line of valleys Possera and Pavone streams.

The village built on a steep hillside, with its stone houses, narrow alleyways, small arches and steps is undoubtedly one of the most romantic places in Tuscany. 


12 – Anghiari (Arezzo) 
With its colossal walls and winding and steep streets, tunnels and towers, Anghiari is the quintessence of the hills of the Tuscany countryside. It was here, in 1440, on the plain beneath the fortress that is preserved in the town where the Florentine army defeated the Milanese at the Battle of Anghiari. This victory was recreated and celebrated by Leonardo da Vinci in his “Lost Masterpiece”, which now seems to have been found in the Palazzo Vecchio in Florence.

13 – Lucignano (Arezzo) 
Lucignano is a small medieval village overlooking the Val di Chiana, halfway between Siena and Arezzo. It is known for the Tree of Love, a masterpiece of Gothic jewelry decorated with coral, enamel and rock crystal. Its streets and monuments make Lucignano a place that people should not miss on a tour of Tuscany.

If you want to elaborate on Lucignano I recommend reading the following article which includes some information about this magical place: Four Hidden Gems Around Siena.

14 – Castiglion Fiorentino (Arezzo) 
Situated between Arezzo and Cortona, Castiglion Fiorentino origin dates back to the Etruscan period. The present appearance is a walled medieval town of the thirteenth century. The town is known for the towers that mark the boundary of the old city. The central Town Hall Square is the heart of the city where, under the arches built by Vasari, one can enjoy a splendid view over the Val di Chiana.


15 – Casole d’Elsa (Siena)

Famous for its rolling hills, vineyards and olive groves Casole d’Elsa is at an altitude of 417m and has a population of about 3,000 inhabitants.

Visitors can enjoy a visit to the church of Santo Spirito and Palazzo Pretorio (old town hall), which is decorated with coats of terracotta from noble families throughout the centuries that have ruled the town. Other places of interest are Palacio Casolani – Berlingheri – Scheggi, the Collegiate Church of Santa Maria Assunta and the church of San Pedro and San Nicolas.

16 – Castelnuovo Berardenga (Siena) 
Castelnuovo Berardenga, situated near Siena, is a medieval village famous for its villas and the beautiful gardens. In fact, the city and its surrounding area breath charm, character and history. Castelnuovo Berardenga in the Chianti wine area is also an excellent starting point to explore this wine region of Tuscany. 

17 – Cetona (Siena)
Between the Val di Chiana and Val d’Orcia close to the boarder with Lazio and Umbria is where travelers will find the town of Cetona. The town is a resort chosen for personalities from various fields to enjoy their vacation in complete tranquility and far from the main tourist routes. 

18 – Chiusi (Siena)
Chiusi is a very small town in the southern province of Siena and has numerous places of interest among which are: an extraordinary necropolis, the labyrinth of Porsenna, and the NationalArchaeological Museum, which houses a treasure trove of Etruscan findings and Greek and Roman pottery.

The Etruscans of Chiusi worked a special type of ceramic, a ceramic called Bucchero that is very dark and imitates metal.

Chiusi Lake (located northeast of the city) is a perfect place for nature lovers and sport. Among the products of the earth, we must mention without a doubt the olive oil DOP Terre di Siena and the wine Chianti Colli Senesi DOCG, IGT Toscana.

For those who want more information can read an article by Sylvia on Chiusi

19 – Montalcino (Siena) 
The town of Montalcino, surrounded by ancient walls, dominates from the top of a hill of Val d’Orcia. Located a few kilometers from Pienza and the Crete Senesi, and not far from Mount Amiata, which is world renowned for its wine, the famous Brunello di Monatalcino.

A fairytale place ideal for a day immersed in the history of the Tuscan tale, this village boasts stunning views over the surrounding valleys.

For those who want to amplify their knowledge I recommend reading the article: The Wines of Tuscany.  

20 – Montefollonico (Siena)

At the top of a lonely hill in front of Montepulciano, sits a picturesque medieval village in Tuscany: Montefollonico.

Its position away from the busy roads and the beaten track Montefollonico makes an especially charming and attractive village for a traveler. Located between the Val d’Orcia and the Val di Chiana, southeast of Siena, the city has ancient origins.

The name itself derives from the Latin word “fullones”, a name given by the Romans to the artisans working with fabric.

The town is well preserved and is surrounded by high walls and guarded by seven cylindrical towers that have remained unchanged over time, along with the beautiful Torre del Cassero, which dates back to the thirteenth-century. Also in perfect condition are the three main entrances of the city, the Palacio de Jusiticia and the thirtheenth-century church of San Leonardo. The old water cistern of the city, found on the main street, is really beautiful.

21 – Montepulciano (Siena) 
Montepulicano is located south of Tuscany, in the province of Siena and is in a limestone hill 605 meters above sea level. It is world famous for its Vino Nobile, a wine of great excellence. In addition to wine there are many things worth visiting in Montepulciano starting with its squares, monuments and cathedrals. The city is known as “the jewel of the sixteenth century” thanks to its splendid typical architectural style of the Renaissance. 

22 – Monteriggioni (Siena) 
The history of Monteriggioni, a municipality in the province of Siena, has ancient origins. The walled city was built on a hill by the Sienese in the eighteenth-century to protect their defensive line against their historic rivals, the Florentines, who sought to expland their borders.

Considered one of the best-preserved medieval towns in Italy, Monteriggioni boasts magnificent walls of the majestic fourteen protruding towers.

Monteriggioni is important both architecturally and culturally and has been mentioned in the Inferno of DanteAlighieri’s Divine Comedy.

The town of Monteriggioni seems suspended in time. As you enter through one of two doors and you are in the heart of the village. The main square is called Piazza Roma (Rome Square) and there is the Church of Santa Maria Assunta, which combines Romanesque and Gothic styles. The village is small and consists of wine shops, gun shops, medieval and small hotels and restaurants serving traditional Tuscan cuisine and wine of the area. 

23 – Murlo (Siena)

Murlo is an ancient small medieval village in the Metallifere hills and near the river Crevole. In Murlo there are many monuments and historic buildings to visit; from the municipality, the castle and the Church of San Fortunato and Palazzone. The archaeological site of Poggio Civitate where they have unearthed many Etruscan remains very close by. 

24 – Pienza (Siena)

Pienza is a small town located in the Vald’Orcia, in the southern part of Tuscany. It is only 15km from Montepulciano and 20km from Montalcino; two places worth visiting in this area. Known as one of the jewels of Italian Renaissance Pienza was built by architect Rossellino and financed by Pope Pius II of the Piccolomini family.

For further information about Pienza I suggest reading the following article: Visiting Pienza.

25 – Bagno Vignoni (Siena) 
Immersed in the beautiful Val d’Orcia at the foot of Mount Amiata lies this small spa town. The village, perfectly preserved in its main square retails a large thermal bath which is not open to the public.

In the Posta Hotel located in the same village there is access to the hot springs (for a price), however, in the summer you can enjoy outdoor hot springs just outside the village.

For further information regarding location I recommend the following reading: Bagno Vignoni.

26 – San Quirico D’Orcia (Siena) 
Halfway between Pienza and Bagno Vignoni in one of the most beautiful roads in the whole of Tuscany is located the town of San Quirico D’Orcia. The village and others of the area retain a medieval appearance.

27 – Radda in Chianti (Siena)

Radda is the so-called “Triangle of Chianti”, comprising the municipalities of Castellina in Chianti, Radda in Chianti and Gaiole in Chianti. Chianti medieval village located in the centre of a beautiful hillside, Radda is an excellent base for exploring the Chianti area and its castles such as Brolio and Meleto.

For further information on this area you can read the following article: Radda in Chianti and the "Gallo Nero".

28 – Radicofani (Siena)

In the south of the beautiful Natural Park of the Val d’Orcia boarder, one of the most impressive and spectacular medieval fortresses in all of Italy rises. For centuries, the imposing Fortress of Radiconfani has been the symbol of the defense and control of the Via Francigena, on the boarder between Tuscany and Lazio. Radicofani besides being of great military importance was also an obligatory stop for pilgrims and travelers.

This powerful fort was built in 978 AD, although its origins date back even further in time. Before climbing the tower I recommended a walk in the pine forest which surrounds the fortress, where you can see the remains of arches and wells partially hidden by vegetation at first sight.

The majestic tower of 37 meters high and rebuilt in the last century, boasts wonderful views across the park of Val d’Orcia and Mount Amiata.

The vast and overwhelming panorama can be classified as one of the most beautiful of Tuscany; the view tretches to the mountains of the Apennines, Lake Trasimeno and Lake Bolsena. 

29 – San Gimignano (Siena) 
San Gimignano needs no introduction. Known worldwide for its high towers is one of the most visited towns in Tuscany and all of Italy. In the Middle Ages, this city was defended by 72 towers, which only 15 of them are now preserved. These towers, a symbol of power of the wealthiest families of the city, are part of the UNESCO world heritage.

For further information on this town I recommend reading: San Gimignano: the City of the Medieval Skyscrapers


30 – Trequanda (Siena)

The medieval village of Trequanda is located in one the most pristine areas of the province of Siena and extends around a thirteenth-century castle. Trequanda is located on a hill, immersed in a natural setting of forests vineyards and olive groves.

The historic centre dominated by the splendid Romanesque church dedicated to St. Peter and St. Andrew was built in the thirteenth-century. The façade is of white stone slabs and inside there is a “Ascension” with frescoes by Giovanni di Paolo. 

31 – San Casciano Bagni (Siena) 
This town is of Etruscan origin and its name reflect the presence of hot springs (Italian for Bathrooms is Bagni. Legend has it that Porsenna, the Etruscan ruler of Chiusi, bathed in the hot springs. The thermal waters of San Casciano dei Bagni containing sulfur, calcium and fluoride, have anti-inflammatory and analgesic properties. Through inhalation which works with the respiratory system with anti-inflammatory effects. They also have a ”peeling” effect on the skin.


32 – Fosdinovo (Massa Carrara)

Fosdinovo is a town of Massa Carrara, located about 15 km northwest of Massa.  Fosdinovo owes its importance in history of its natural location between the sea and the mountains, the village is a hotspot between ports and inland areas of the region.

Founded by the Romans significantly increased the shelf life of the area. Since the Middle Ages, Fosdinovo is strengthened thanks to the most powerful family in the Lunigiana Malaspina and even Dante, the great poet, lived for some time in Fosdinovo.

The opening to the sea was at the same time the fortune and misfortune of Fosdinovo: first the opportunity to earn money from trading, on the other hand, it was the front line in time of wars and struggles, including the two World Wars.

Fosdinovo is today a village rich in art and history that undoubtedly deserves a visit.


33 – Massa Marittima (Grosseto) 
Massa Marittima is a jewel of Tuscany. Beautiful city with panoramic views located just 50 km from Grosseto in southern Tuscany. The historic centre of the city is of Etruscan origin and many signs of the past are still recognizable in the perfectly preserved walls, the narrow streets and in urban and architectural complexes. The history of this place is strictly linked to mining because there are mines of iron, mercury, lignite and copper here.

34 – Pitigliano (Grosseto)

Pitigliano in the Maremma is hallway between Florence and Rome on top of a volcanic tuff. Its unmistakable profile makes it stand out kilometers away with its unique charm which is almost surreal. It is also known as Little Jerusalem (Piccola Gerusalemme) due to the presence throughout the history of an important Jewish community, Pitigliano has an interesting historical and cultural past.

About Pitigliano you can read the following article: Pitigliano - Off the Beaten Beauty.  

35 – Sorano (Grosseto)

Sorano is a picturesque village situated on a hill slope hanging from tufa stone. Of Etruscan origin Sorano preserves a beautiful old town. Wandering through its streets and enjoying the beautiful views over the valley is definitely an experience that travelers should not miss.

And so far that’s all!

I tried to mention the most important towns and I apologize for missing some because I am certain there are more that are wort emphasizing.

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