Where in Tuscany? The Best Areas to stay in Tuscany

By 23 Gennaio 2014 Tourist Info

Anyone planning a holiday in a completely new country soon wonders as to where is best to go. Which part of Tuscany is better to visit? Which are its best destinations? what’s the best place to pass a fantastic holiday in Tuscany?

Tuscany is one of the most beautiful and fascinating regions of Italy and the world; one of the richest regions of Italy for its unparalleled art, culture and suggestive landscape. It’s an important holiday destination for tourists from all over the world, able to meet anyone’s requirements: sensational landscape, medieval hilltop towns, beautiful beaches and islands, thermal springs, countless masterpieces of art, museums of any kind, delicious food, great wines, and unique manufacture.

Where to go in Tuscany?

Tuscany is quite a vast and varied region of exceptional beauty, but we need to say that some areas of Tuscany are more beautiful than others, and some (though very few) are not particularly attractive to stay.

What follows here is a personal view on which are the best areas to stay in Tuscany, that surely deserve to be visited and are also ideal to have a wonderful vacation, staying in a charming hotel or rustic farmhouse. We’ve made a general selection of major areas to visit in Tuscany, that represent the region at its best!

The best parts of Tuscany to stay in

1. Florence and the Chianti area

Ponte Vecchio in Florence

One of the first things that soon springs to mind thinking about Italy and Tuscany is the immense artistic treasures to be found in Florence: its impressive Cupola, Piazza della Signoria with the Loggia dè Lanzi, Palazzo Vecchio, the unique paintings at the Uffizi, the Ponte Vecchio, the beautiful artisans’ shops and many other wonders unique in the whole world!

Moving southeast of Florence, you soon find yourself immersed in the so called Chianti region, stretching in the very heart of Tuscany between the provinces of Florence, Siena, and Arezzo. This part of Tuscan countryside is well known all around the world for one of the most famous wines of Italy, Chianti of course, but also for its natural and artistic beauty.

On its green rolling hills rise thick forests, lush vineyards and olive trees, which create a unique spectacular panorama. Old churches, castles, medieval villages, monasteries, villas and old farms are evidence of a land with a long history in the Middle Ages, a strategic country that was always contested between Siena and Florence, until when, in the sixteenth century, the Medici family imposed their hegemony over the whole of Tuscany.

The Chianti region in central Tuscany

Driving on the Via Cassia one can imagine the tiring journeys of merchants and pilgrims from northern Europe on their way to Rome, while admiring the buildings along the route: abbeys, churches and castles, all beautifully preserved. On the Via Cassia you meet the villages of San Casciano Val di Pesa, Barberino Val d’Elsa e Tavarnelle Val di Pesa.

Another important route crossing the Chianti is the Via Chiantigiana. Compared to the previous one is a more natural and scenic road, winding across all those enchanting and spectacular vineyards. Driving along the Via Chiantigiana, you meet some of the loveliest and charming medieval hill villages of Chianti, like Greve in Chianti, Castellina in Chianti, Radda in Chianti, and Gaiole in Chianti. You can stop to visit them and take some rest at a local restaurant enjoying great food and wine.

Moving west of the Chianti villages, you then find San Gimignano, located in the Elsa valley but still part of the Chianti area, that is one of the most popular medieval town in Italy. Known for its beautiful 14 surviving towers and the great local products, this picturesque tiny village can be a perfect base for part of your stay, considering its strategic location amid some of the best sights and destinations of Tuscany.

2. Siena and the south – Crete Senesi and Val d’Orcia

View from the Facciatone of the Duomo in Siena

After Florence, Siena is the richest artistic town of Tuscany. After visiting Florence, you will literally get surprised by Siena, as the two Tuscan towns are deeply different from one another. Florence is mainly a Renaissance town stretching on a plain, while Siena is thoroughly medieval and rises on a hill top amid the countryside.

This fantastic destination in Tuscany, dominated by the red color of its bricks, is mainly known for the Palio horse race, great event for the Sienese people. Piazza del Campo, unique for its particular shape in the form of a shell, is the beautiful setting for the race. But Siena is not just the Palio. It’s enough you enter its historic center to be literally bewitched by its irresistible suggestive atmosphere.

You really need to go there to understand! The attractions of Siena are stunning; from the Torre del Mangia and the Palazzo Pubblico with its fantastic museum, to its spectacular Duomo and Santa Maria della Scala. You can read more about Siena and its treasures here. In case you are traveling by car, I suggest Siena and not Florence as your home-base to explore Tuscany 🙂

In this case you can read about the best day trips from Siena.

Val d’ Orcia! There are countless artists, from the past as well as from the present, that have been fascinated by this spectacular idyllic valley in the territory of Siena. Many Renaissance painters, but also poets, writers, and even directors of international cinema, have been inspired by the landscapes and the rural life of the Val d ‘Orcia. Just think to “The Gladiator”, or “The English Patient”.

Valdorcia in Tuscany, Italy

Each element in this valley contributes to give it a peculiar charm, making it an enchanted land, a rare beauty. The scenery of the Valdorcia is made unique by various factors; hill towns and ancient villages, natural terraces overlooking the valley, stunning views ranging from the Apennines to the Tyrrhenian Sea, wild Mediterranean vegetation, fields in bloom, wild orchids, rows of cypress trees guarding ancient country roads, forests of oak and chestnut trees.

To make this paradise of Tuscany even more fascinating there’s the Mount Amiata, the highest extinct volcano in Italy, valuable source of clear waters and dotted with many picturesque villages like Abbadia San Salvatore or Santa Fiora.

This amazing land is home to some of the most beautiful smaller hill towns of Italy: Pienza, Montalcino, Bagno Vignoni, San Quirico d’orcia, Castiglione d’Orcia, and radicofani. Read about the Top Ten Sights to visit in Val d’Orcia here.

Soon south of Siena and before reaching the Val d’Orcia, you come across the arid and peculiar territory known as the Crete Senesi. During the Middle Ages all this area was known with the name of Desert of Accona. This strange name was due to the particular scenario of its semi-deserted territory, beautiful hills but almost completely bare of vegetation, consisting of scattered trees here and there, and characterized by calanchi and biancane, particular geological formations of the land.

The evocative landscape of the Crete is dominated by characteristic hill-top villages, like Asciano, Buonconvento, Rapolano Terme, and San Giovanni d’Asso, this last famous for its white truffle. Rapolano Terme is a splendid thermal destination in Tuscany, its thermal pools are simply paradisiac.

Near Asciano, rising on a spectacular outcrop amid a wild nature, is the real treasure of the Crete, the Abbey of Monte Oliveto Maggiore. You can read more about the abbey and the main sights of the Crete Senesi here.

3. Maremma and the Tuscan Coast

Tuscan Coast in Maremma

The Maremma is one of the wildest and most fascinating areas of Tuscany. Maremma means sea, nature, relaxation, thermal waters. It is a land rich in traditions, history, art and culture. A mix of elements that makes this area in southern Tuscany, an ideal tourist destination. If you love riding horses you are in the right place, the same if you love biking or trekking; there are beautiful itineraries and hiking trails both on land and at the sea.

You can go exploring the picturesque pine forests of Castiglione della Pescaia and Marina di Grosseto, you can wander amid the wild nature of the Uccellina Park overlooking the deep blue sea, you can lie under the sun at the beaches of Feniglia and Giannella, and at all the other beautiful bays of Monte Argentario.

The trip to Maremma’s secret places can become even more interesting and suggestive by exploring its many archaeological Etruscan sites, the necropolis, the Vie Cave: the fortresses. You will get amazed by the ancient city of Roselle, Vetulonia, Sovana, Sorano and Pitigliano. You can walk along the ancient pathways of the many exquisite medieval towns, remained unchanged over the past eight hundred years! and finally you can admire the forts that defended the Argentario coast from pirate attacks of the Saracens; ancient Maremma is an endless resource to be discovered.

The most beautiful coastline of Tuscany is probably in its southern part from Castiglioncello to Monte Argentario. The sea of Tuscany is of exceptional beauty. Just think to Elba, Giglio, and Giannutri islands, and to Talamone, Castiglione della Pescaia, Punta Ala and Follonica, authentic jewels! Protected beaches, crystal clear water, wild bays, marinas, nightlife, water sports: in Maremma you will also find everything for a great vacation at the seaside.

4. Valdichiana – Cortona and Arezzo

Arezzo, art town in Tuscany

The Val di Chiana is a large beautiful valley that stretches between the provinces of Arezzo and Siena in Tuscany. The landscape is mainly hilly, though there are major peaks reaching about one thousand meters.

Here you can start to explore wonderful art towns like Arezzo, Civitella in Val di Chiana, Cortona, Foiano della Chiana, Lucignano, Monte San Savino, Cetona, Chianciano Terme, Chiusi, Montepulciano, Sarteano, Sinalunga, Torrita of Siena and Trequanda. All of these hilltop towns and villages are particularly charming.

Montepulciano is one of the most perfectly preserved towns in Tuscany, with beautiful and elegant palaces, fortresses, piazzas, and stunning vistas. Montepulciano can be a perfect base for your holiday in Tuscany.

Cortona is incredibly captivating, on the very peak of a panoramic hilltop, Cortona is a very ancient Etruscan town all to discover. The panorama here is endless reaching up to Umbria and the Trasimeno Lake.

Arezzo, the city of La Vita è Bella by Roberto Benigni is one of the major art towns in Tuscany, with a particularly suggestive and scenic piazza with loggias.

If you are also looking for some relax and wellness, head on to enjoy the thermal springs and spa at Montepulciano or at Chianciano Terme, renowned thermal destination in Tuscany. Sarteano, Chiusi, Cetona, and Lucignano are less known villages, that are extremely appealing and all to discover.

Of course Tuscany has many other areas that are beautiful like Mugello, Casentino, Lunigiana, Valdinievole, and Garfagnana, but again the one above is my wish list 🙂

Need help in planning your holiday in Tuscany? Looking for the best suggestions as to special places to visit and fantastic accommodations? Ask a question! It’s free!

One Comment

  • Grace Jones ha detto:

    Hi Elena, I love your blog…
    A friend and I are travelling through Italy to France in August. We would like to see some of the main cities but also some villages off the beaten track as well. We are also hoping to stay in Airbnb’s as we are on a tight budget. We would really like to stay at the Cinque Terre region or somewhere with beautiful views if possible but are open to suggestions. We will have a car and will have around a week to travel in this area…. can you PLEASE guide us to the places that will make this trip amazingly special?

    Thanks in anticipation Elena… your advise will be much appreciated 🙂

    Kind regards
    Grace Jones

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