A taste of medieval Tuscany towns and more! With this guide, I will let you discover the best towns in Tuscany. Explore Tuscan towns among nature, food & wine, culture!
Tuscany region in Italy is famous for its medieval towns and villages, many of which have been fortunately preserved over time.
Strolling through Tuscan towns gives you the chance to get in touch with the history and traditions of the place, while enjoying breathtaking landscapes in an absolutely peaceful atmosphere.
The local food and wine is also very important, with its typical foods and dishes that will make you fall even more in love with these lands.
Tuscany towns: here are the best Tuscan towns to visit!
Towns in Tuscany are an important historical and artistic heritage. Not only medieval villages, but also many villages dating back to Etruscan times or Renaissance times.
Situated in the hills, along the coast or in the hinterland of Tuscany, the landscapes that surround them are varied but always fascinating.
This last characteristic is one of the reasons why Tuscany towns can be visited in any season: Winter or Summer, Autumn or Spring. Choose the best period for you, take a map and enjoy the best Tuscan towns!
Now I will show you a selection of the best towns in Tuscany, each one with its own particularities and characteristics, its history, culture, food and wine. Let’s explore the best of Tuscany!
Towns in Tuscany, walking in the province of Siena
Our journey through the cities of Tuscany starts in the province of Siena. We are in the heart of the region, immersed in unspoilt nature and valleys. These hill towns of Tuscany offer landscapes that you will hardly forget.
Buonconvento is one of the typical medieval Tuscan cities, with its 14th–century city walls housing the charming historic centre. Visiting this fantastic town, walking along the main Via Soccino, you can admire monuments such as the Church of Saints Peter and Paul or Palazzo Pretorio with its Civic Tower. Lose yourself in its alleys and you won’t regret it!
In Tuscany towns like Cetona must be visited at least once in a lifetime. Its structure is organised in wide paved streets called “coasts” and very narrow alleys. The nerve centre of the town is Piazza Garibaldi, a large square designed by Luigi Vitelli. The Collegiate Church of the Holy Trinity is worth a visit, as is the Civic Museum of the Prehistory of Monte Cetona.
3. San Casciano dei Bagni
This tiny village is one of the oldest towns in Tuscany. Famous for its thermal baths, San Casciano dei Bagni offers as attractions Piazza Matteotti, from which you can observe a breathtaking view over the Tuscan countryside, and the Church of the Conception with an important fresco by “Pomarancio”. If you are looking for a place to relax, this Tuscany city is for you!
Known throughout the world for its wine, Montepulciano is one of the best Tuscan towns. The centre of the town is Piazza Grande, which can be easily reached by following “il corso”, a very evocative long road. A must-see, outside the walls, is the Church of San Biagio, a true Renaissance masterpiece.
Before you go, enjoy a winery tour to discover how this wonderful wine is made.
Pienza is a very small town in the Val d’Orcia, in the province of Siena. Thanks to its position on top of a hill, this Tuscan village offers visitors unique views, definitely not to be missed. Founded as an ideal Renaissance town at the behest of Enea Silvio Piccolomini, who later became Pope Pius II, this town is one of the best towns in Tuscany.
The Duomo is one of the most important buildings in the town, not forgetting Palazzo Piccolomini and the Pieve di Corsignano, which can be reached by a pleasant walk. If you decide to visit this land in September, don’t miss the traditional “Fiera del Cacio” (Cheese Fair).
In Tuscany towns such as Montalcino are considered staples of the local wine-making tradition. The famous Brunello is in fact one of the most important wines produced in these lands, together with Chianti and Nobile di Montepulciano.
Montalcino, however, is not only wine but also history and art. Inside the historic centre, the majestic 14th–century fortress takes centre stage, offering an enviable view from the top of its ramparts. Other characteristic buildings to see are the Palazzo dei Priori with its long, narrow tower, the Church of Sant’Agostino and the Civic and Diocesan Museum of Sacred Art.
7. San Gimignano
San Gimignano is undoubtedly one of the Tuscan towns to visit, thanks to its medieval style, as evidenced by the numerous towers. The symbol of the town is the Cathedral of San Gimignano, which contains important frescoes on the New and Old Testament. Piazza del Duomo, a meeting place for citizens and tourists, Piazza della Cisterna and the Rocca di Montestaffoli are also very beautiful.
Situated in the province of Siena, it is one of the best hill towns in Tuscany. This Tuscan village has kept its walls intact, one of its main fascinating features. In addition to the walls, there are fourteen towers and two gates, Porta Franca and Porta S. Giovanni. Walking through the town’s alleyways, you will reach Piazza Roma, overlooked by the Pieve di Santa Maria Assunta, a small church considered the centre of village life. Don’t miss the walk along the walls, where you can enjoy unforgettable and breathtaking views!
Medieval Tuscan cities: which towns to visit in Florence and Arezzo?
Let’s continue our itinerary to discover the most interesting cities in Tuscany moving between Florence and Arezzo. The landscapes that await you will make you fall in love with these lands, not to mention the fascinating villages I will tell you about. You just have to keep reading!
Anghiari is located in the province of Arezzo, on the border with Tuscany and Umbria. Situated on a gravel hill, this beautiful village retains its typical medieval appearance with its 13th century walls and the imposing Campano Tower. Not to be missed are the Museum of the Battle of Anghiari and the Church of the Cross.
Situated in the hills of the Valdichiana, this small Tuscan village is a pearl of Central Italy. Its perfectly preserved historic centre is practically its main attraction.
Inside you can see the Church of San Francesco and the Collegiate Church of San Michele Arcangelo, two wonders that must be seen. Outside the walls are the Fortezza Medicea and the Sanctuary of Santa Maria delle Querce. If you find yourself in Lucignano in spring, don’t miss the Maggiolata, a festival when the four districts of the town compete with floats.
Cortona, in the province of Arezzo, is one of the best Tuscan villages to visit. Thanks to its strategic position, it offers a series of suggestive views over the Valdichiana and Lake Trasimeno. The centre of the village is, as is often the case, a square: Piazza della Repubblica. Buildings definitely worth a visit include the fantastic Sanctuary of Santa Margherita, the town’s patron saint, and the Fortezza del Girifalco, on the highest point of the hill.
Moving on to the province of Florence, a very interesting village to visit is Certaldo. This town, Boccaccio’s birthplace, is a symbol of medieval Tuscany. Strolling through the town’s alleyways, I recommend you see Palazzo Pretorio with its coats of arms, the symbol of the many families that ruled these lands, and Boccaccio’s house. Don’t forget to visit the Church of Saints Jacopo and Filippo and, if you love nature, the Parco della Canonica!
Montefioralle is a very small village in the province of Florence, in the Chianti region. This town is famous for its particular soil conditions, which make it perfect for grape growing. On its slopes, in fact, there are many vineyards that follow one another and fill the surrounding valleys. In addition to the wine aspect, Montefioralle offers beautiful alleys and the Pieve di San Cresci, located near the village.
In Tuscany towns like Montaione should absolutely be visited. Located in the Val d’Elsa, not far from the most important Tuscan cities, this fantastic village offers a lot from the historical and cultural point of view. The Palazzo Pretorio and the Church of San Regolo are the most characteristic buildings in the town, not forgetting the Longobard settlement of Castelfalfi.
Montaione is also famous for its glassmaking, a tradition dating back to the 13th century and linked to the production of bottles, flasks and cruets.
The best Tuscan villages near Lucca, Pisa and Livorno
Continuing counterclockwise through Tuscany, after passing through Siena, Arezzo and Florence, you arrive at three important cities: Lucca, Pisa and Livorno. Are you ready to discover which fantastic Tuscan towns you are missing? Let’s go!
1. Castiglione di Garfagnana
This fortified village in the province of Lucca still retains its medieval structure, with the fortress and towers dominating the whole town.
Inside the village you can see the Church of San Pietro and the Church of San Michele, both thousands of years old and absolutely beautiful. If you visit the Parco della Rimembranza you can reach the Torrione della Brunella, from which you can enjoy a breathtaking view of the surrounding valleys.
If you find yourself in these places to visit in Tuscany, you must absolutely taste the spelt PGI, the excellence of the village.
Moving from Lucca to Pisa, just a few minutes by car, you can get to Volterra, one of the oldest towns in Tuscany. Of Etruscan origin, it still preserves important buildings such as the Porta Diana, the wonderful Acropolis and the Porta all’Arco.
You can not leave Volterra without seeing the Duomo and the Baptistery of San Giovanni, inside of which there is the Ascension of Nicolò Cergignani. This village is also famous for its alabaster and for being the centre of filming of some scenes of “Twilight”.
3. San Miniato
Also in the province of Pisa is another characteristic village in Tuscany. San Miniato is an Etruscan-Roman town, famous for its white truffle and its fantastic monuments.
The Fortress of Frederick II dominates the city from the top of the hill, but the symbol of the city remains the Tower of San Miniato, built by the emperor himself in the 13th century. The Cathedral of Santa Maria Assunta and San Genesio, as well as the Convent of San Francesco are also worth seeing.
Moving from Pisa towards the sea you will arrive in Livorno, one of Tuscany’s seaside destinations. In the province of this city, there is a very charming Tuscan village, Suvereto. The name derives from the fact that in these lands there are many cork trees, in the local dialect “suvero”. The town’s symbolic buildings are undoubtedly the Town Hall and the Church of San Giusto Vescovo.
5. Castagneto Carducci
Castagneto Carducci is a modestly sized village nestled in the Maremma near Livorno, in the heart of the Etruscan Coast. Walking through the streets of the village, as well as enjoying breathtaking views, you will have the opportunity to admire the Town Hall and the Castle. The Church of San Lorenzo and the Church of S.S. Crocifisso are also very important.
A hamlet of this municipality is Bolgheri, a real jewel among Tuscan towns. Since it is a small village, you will be able to visit it by simply losing yourself in its alleys. Don’t miss the historic centre with its monuments and the WWF Oasis Padule di Bolgheri. This area also produces the famous Sassicaia, one of the most sought-after wines in the world!
The best towns in Tuscany near Grosseto
Our journey concludes with the best Tuscan villages in the province of Grosseto. Descending from Livorno towards Lazio, you will arrive at this other fantastic location, famous worldwide for its landscapes and towns. You just have to discover one last selection of the medieval cities in Tuscany!
Situated in the province of Grosseto, Pitigliano is one of the most beautiful towns in Tuscany. It is located on a tufa spur that makes the atmosphere very suggestive, almost surreal. Nicknamed “Little Jerusalem” for its large Jewish community, Pitigliano offers its visitors interesting buildings such as the Synagogue or the Medici Aqueduct, not to mention the Cathedral of Saints Peter and Paul.
Capalbio is a small town in the province of Grosseto, located between the Maremma countryside and the sea. The historic centre can only be visited on foot, but it is well worth the effort! Inside you can see the Aldobrandesco Castle, the Church of San Nicola and the Oratorio della Provvidenza. Around Calpabio, don’t miss the WWF Oasis Lake Burano and the beautiful Tarot Garden.
This Tuscany city is world famous for its important production of PDO extra virgin olive oil. One of the most important attractions is the “Olivo nel Cisternone”, the largest plant in the world fed by aeroponic technology and the first example of Olivastra Seggianese variety. If you visit this town, you must see the Corpus Domini Church and the Sanctuary of the Madonna della Carità.
What to do in a Tuscany city
If you have read this article so far, I don’t need to tell you that there are many activities that can be undertaken. Thanks to the landscapes offered by these lands, you can organise fantastic walks, bike rides or horseback rides surrounded by nature.
In Tuscany, the land of wine and olive oil, you can visit prestigious wineries or go wine-tasting, take part in local cookery courses and (of course!) visit some of the best Tuscan towns!
Cities in Tuscany: food, wine & events
Tuscan food and wine is one of the most varied in the country. We start with the typical unsalted bread, also used for one of the most famous recipes, the Ribollita.
As far as first courses are concerned, we have “strozzapreti”, “pici” and “testaroli” with pesto, which you should absolutely try!
You can’t leave Tuscany without tasting the Lardo di Colonnata, Finocchiona and caciucco. Finally, in addition to the endless supply of olive oil and wine, try cantucci biscuits and panforte.
As events to see, in addition to those already mentioned in this article, I recommend “the Livorno rowing races”, “Cortona on the Move” and “the Feast of Santa Croce”.
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