Five Best Towns in Tuscany

Tuscan Hill villages to explore and stay in

We all have the mental image of rolling hills with little villages perched on top, red roofs clustered together with a couple of church bell-towers pointing to the sky, sometimes protectively surrounded by ancient stone walls. Some say that the Tuscan hill villages were constructed on hilltops for defence, others that it was to avoid malarial mosquitoes, others yet that the bronze age populations wanted their altars to be as close to the heavens as possible.

All this has had the happy result of the picturesque tradition of towns and villages topping the craggy hills of green Tuscany, enjoying panoramic views and developing a particular form of building suited to climbing down hillsides like the icing on a cake. These towns have small communities with a life of their own. There is a tangible sense of history living in the stones and in the faces of the population. Of necessity self-sufficient in the past, the villages continue their tradition of local craftsmanship, keeping them alive and vibrant. The continuance of village life also has the happy effect of conserving the very many local festivals, from opera to horse-races, and the local food specialities such as wild boar, mushrooms or whatever is in season, the celebration of which give an excuse for enormous open-air feasts and dancing under the stars.

Here are our favourite 5 to visit, stay in and explore. They are not the most famous, but they each have something we think of as special, as well as being off the beaten track.

1. Fivizzano

Fivizzano is not a classic Tuscan town, and that's part of the reason I like it. It's in the mountain ranges in the north of Tuscany, with steeper valleys, darker stone and a slightly different architecture from the rest of the region. These are interesting places to explore, with villages that feel forgotten by time, roads that switchback their way up steep slopes and fantastic mountain walks.

Fivizzano main square

Fivizzano has a great old square, with a baroque fountain in the centre and an excellent ice-cream shop on one side, and the Caffe Elvetico on the other. I've spent many happy hours sitting here watching the world go by with an Americano, or a Prosecco, in hand. This is a town to relax in, where time seems to slow down and dilate. When you need to explore, you can take a slow train through the mountains to Lucca, or even drive to the coast in 30 minutes - and then return to this haven.

Where to eat in Fivizzano

  1. Caffe Elvetico. This is in the main square - part of the pleasure is sitting in the square watching the world go by. Via Vittorio Emanuele Ii, 14, 54013 Fivizzano MS, Italy
  2. Bar Ricci. Also in the main square, Bar Ricci is the place to go for icecreams. Bar Ricci
  3. Osteria dell'Aviatore. Rated well, I haven't eaten there yet. Via Umberto I, 26/42, 54013 Fivizzano MS, Italy
  4. Ristorante di San Paolo. A great restaurant with a large terrace on the road to the pass. SS63, 63, 54013 Fivizzano MS, Italy

Where to stay near Fivizzano

Ponte Romano,

an old stone house set by the mule path that used to be used to climb up to the mountain passes and into Emilia Romagna. Today it is reached by crossing an ancient stone bridge on foot, locally called the "Roman Bridge" or "Ponte Romano" - which is what we also called the house:

Ponte Romano - villa for 8
Ponte Romano - villa for 8 with pool in Lunigiana

2. Civitella in val di Chiana

The "take your breath away village": the views from here are spectacular, looking out over the Chiana valley, very large by Tuscan standards, wide and spacious with the Chiana canal running south towards the Tiber. The valley is home to the famous "Chianina" cattle, large, white and beautiful. They were used by the Romans in the triumphal processions because of their majesty and colour - today they're probably best known as the source for the fabulous "Fiorentina" steaks.

Civitella sits on a forested ridge high above this wide and spectacular village, with a fortified "Rocca" still punching into the sky on the highest point. You can really feel the privilege of the position chosen by the first inhabitants of this well-defended spot, with a full view of anybody approaching across the valley. Today it has some good restaurants and is a great place to visit, away from the crowds and still largely untouched.

Where to eat in Civitella in Val di Chiana

  1. Osteria Antico Borgo. Piazza Lazzeri, 52041 Civitella in Val di Chiana AR, Italy
  2. La Botteghina di Civitella. piazza Mazzini, 5, 52041 Civitella in Val di Chiana AR, Italy

Where to stay near Civitella in Val di Chiana

Read this delightful account of a stay in

Casa Allioni

and visiting Civitella by a client of ours, the Travelling Lawyer.

To be closer to the village you could stay in


within walking distance of the village - or if a larger group, why not stay in the beautiful


a big old rambling farmhouse with 3 apartments - but great taken by a large family group.

View of Civitella from Guardiano
View of the old castle of Civitella from Guardiano

3. Radda in Chianti

Chianti is on everybody's list - if only for the siren call of the wine. Radda was one of the founding towns in the "Chianti League". The centre is small and pedestrianised, with plenty of good restaurants and cafes. Like Casole and Civitella, Radda stretches out along a hill ridge, with the "Palazzo del Podestà" (the Town Hall) facing the church of San Niccolò across the main square. The town also has a small museum, based in the former monastery of Santa Maria in Prato - their collection includes an altarpiece by Neri di Bicci, the last of three generations of Bicci painters in the 14th and 15th centuries.

Church of San Niccolo in Radda
Church of San Niccolo in Radda in Chianti

Radda's wealth is seen in its many 15th & 16th century palaces which rise amid the medieval buildings. From the Piazza Ferrucci, in which are located the Palazzo Pretorio and Romanesque church of San Niccolò, to the circuit of its fortified walls and the cultivated landscape beyond, it is obvious that Radda knew its livelihood was wed to agriculture. This area appreciates its artists, be they the ancient ones whose gold smithing and stained glass can be admired in the Romanesque church of Santa Maria Novella, dating back to the year 1000, or the fanciful modern sculptures peeking out of the woods in the Parco Sculture del Chianti in nearby Pievasciata.

The perfect spot to base yourself to explore local vineyards, Radda sits in the very heart of the region known as Chianti, a hilly region between Siena and Florence where every slope seems to be either covered in dark forests of evergreen oak, shimmering lines of olive trees or, most likely, draped in trained lines of vines lovingly tended for their grapes. To read more about Chianti wine and its origins, have a look at What is Chianti wine.

Where to eat in Radda

  1. Il Girarrosto. Via Roma, 35, 53017 Radda in Chianti SI, Italy
  2. La loggia del Chianti. Via degli Ulivi, 1, 53017 Radda in Chianti SI, Italy

Where to stay near Radda in Chianti

We have a beautiful large house within walking distance of Radda - it's very popular with families as there is plenty of space to play and explore in the houses large grounds, but ice-creams and restaurants are just a short walk away.


available for 14, 10 or even just 8 but still always private.

Outdoor dining at Docciole
Outdoor dining at Docciole, close enough to oversee the pool as you sip your Chianti

For more houses in and around Chianti see our Villas in Chianti.

4. Cortona

Made famous by Frances Mayes' "Under the Tuscan sun", Cortona is a hill-town with a long and important history; there has been a settlement here for close to 3000 years! With great pedigree come great origin-stories and Cortona has a fabulous one, first recorded by Annio da Viterbo in the 16th century. According to Annio, Noah first came to the Chiana valley 108 years after the great flood and settled here for 30 years. His son Crano climbed onto the hill on which Cortona now sits and liked it so much he founded the city, 273 years after the flood.

While there may be some fabrication in this story, we do know that the Etruscans took this city over from the Umbrans and built some fine defending walls, some of which still stand today. But I like it because of its atmosphere: it's the largest of all this list of 5 but still has a small-town feel to it, and like Casole, has a main street, up and down which the locals take their constitutionals of an evening, as well as a museum and some excellent cafes and restaurants.

The views from the town look out over the Chiana valley and towards Lake Trasimeno, just on the border with Umbria. This was the site of a famous battle between Hannibal with his elephants and the Roman army. Hannibal used the slopes below Cortona and closer to the Lake to conceal his forces from the Roman troops, led by an over-eager general, Flaminius. By surprising the Roman troops Hannibals forces prevented them from forming their battle formations and pushed them into the Lake. From the highpoint of Cortona one can imagine how it would have played out, with the landscape laid below like a war-game.

Cortona Palazzo dei Priori

Today the town is a civilised base to explore and to visit, with some beautiful churches and excellent art to see, like the Church of Santa Maria Rotonda by Vasari, and Santa Maria delle Grazie by Francesco di Giorgio Martini.

Where to eat in Cortona

  1. La Bucaccia. Via Ghibellina, 17, 52044 Cortona AR, Italy
  2. La Grotta. Piazza Baldelli, 3, 52044 Cortona AR, Italy

Where to stay near Cortona

The best place to stay to visit Cortona and all this border area between Tuscany and Umbria is


a beautiful house for 6 on the shores of Lake Trasimeno. One of our most popular houses, it has the perfect combination of position, space and charming owners (they live next door) that means many clients keep coming back year after year.

The view from the pool over Lake Trasimeno
The view from the olive groves by the pool, looking over lake Trasimeno

5. Casole d'Elsa

The "Buongiorno" village, this is where I went to school and grew up. There is one main road that runs along the ridge of the hill, with the main church at one end, and the town hall at the other. In the evenings, as in many similar villages, old and young alike walk up and down this main street, perhaps stopping for a coffee or an aperitivo at one of the cafes along the way, smiling and nodding to acquaintances and new visitors alike. A visitor once told me they called Casole the 'Buongiorno' village because everybody seems to smile and say 'buongiorno' (good-day) as you walk down the street. It's a small gesture that can really brighten your day.

Sbandierata di Casole d'Elsa
Casole has a number of local festivals, including its own 'Palio' horse race, with flag throwers in the square and a big village celebration - normally held in early July

The village has a small museum, with some excellent work by the local artist 'Alessandro Casolani', and some interesting finds from the nearby Etruscan tombs. There are a number of cafes, good restaurants like Osteria Casolani, Da Brigante, Il Porrina - and good little grocery shops with local olive oil and fresh vegetables.

Siena, Florence and San Gimignano are all close by, should you wish to explore - many come with big plans then stay close by, enjoying the village, exploring the other nearby villages, going wild-river swimming in the Pavone or Cecina rivers.

Masso delle Fanciulle
Wild swimming in the Cecina at the 'Masso delle Fanciulle'

For more on staying in Casole d'Elsa and wild swimming, read this lovely article by Rebecca Miles:


Where to eat in Casole d'Elsa

  1. Caffe Casolani. Via Alessandro Casolani, 41, 53031 Casole d'Elsa SI, Italy
  2. Dal Brigante. Piazza Luchetti, 53031 Casole d'Elsa SI, Italy
  3. Il Porrina. Piazza della Libertà, 27, 53031 Casole d'Elsa SI, Italy

Where to stay in Casole d'Elsa

We have a number of places to stay in Casole d'Elsa - one of which used to be my house, a lovely flat on the edge of the village, still called

Dan's House.

If you'd prefer a pool, Agriturismo Elvira has some lovely apartments a short walk away from the village, like


For all the properties in the area, have a look here: Villas in the Valdelsa.

Dan's House
The double bedroom looks out over views of the Tuscan countryside, with San Gimigano to the left and the Chianti directly ahead