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Do you want to have a special holiday, away from the frenetic pace and stress of the city? Then, the best Tuscan villages to visit are waiting to charm you with their history and their beauty.

Just imagine you drive around and find yourself from time to time at the foot of fantastic Tuscany small and beautiful towns. Tuscany is a land of hills and arts cities and home to hilltop towns rich in tradition and with hidden gems and wonderful churches. You will be really surprised to see how many possibilities and how many 'moments of pure beauty' this region offers!

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We at toscanainside.com want to guide you through the landscapes and medieval squares of these fantastic villages. Tuscany allows you to wander carelessly and find places to stop for a short time to discover small villages suspended in time and photograph unforgettable views.

You will soon realize that there are numerous towns and small villages to visit in Tuscany: you just have to make a choice! This way, if nothing else, you'll have a more than valid excuse to return! If among your holiday photos there is no shortage of images with the monuments of Pisa or the historic centre of Florence, now it is time for you to dedicate yourself to the places that are around these famous cities. You will discover, in fact, that the borghi in Toscana unite the soul and history of this beautiful region.

To help you with the orientation and to suggest possible routes to Tuscan hilltop villages, we have divided our selection of the most beautiful villages of Tuscany by referring to the capitals of the province to which they belong. You will see, for example, what are the possible and easier trips from Siena or Arezzo. Do not spend your holiday driving around with the sun on your face! This way you can plan your tour in advance and avoid wasting time travelling between the many Tuscan villages which you shouldn’t miss! Are you curious to know the best villages to see in Tuscany selected by us?

Here, are some essential stages and valuable tips from insiders.

  • AREA OF SIENA. Starting with one of the most charming small towns in Tuscany, Siena: you will find unique places famous throughout the world. Between Siena and Colle Val d'Elsa you will find two of the most charming villages in Tuscany, Italy. Tuscany is a land of medieval buildings and spectacular town halls. For examples, which are the best places to visit in San Gimignano? Well, it boasts a spectacle of 14 towers and many Renaissance treasures! On the way to reach this village you should stop in Monteriggioni. Retrace the Via Francigena among the rolling hills of Tuscany and feel the experiences of the medieval pilgrims.

    If your itinerary goes from Siena to the south, you will have before you a path rich in unmissable places. Cross Val d'Orcia (we remember you that it is part of the UNESCO heritage) and you will have the good fortune to stumble across the town of the Brunello red wine, Montalcino, and a village famous for its cheese, Pienza. A stop here is a gift for your taste buds!
    Of all the hilltop towns of Tuscany, these are the most fascinating areas of the region: if you travel along these routes at any time of year and admire the landscapes, you will feel like you are a part of a picture! Seasons, alternating their own colours, give rise to different views: in autumn you will be dazzled by shades of yellow and in spring by the lush green fields of wheat.

    The Siena tour continues with two other villages in Tuscany that you must visit: another town world famous because of its wine, Montepulciano, and Cetona, located near the border with Umbria.

    Please note also, that the most beautiful Tuscan villages are often chosen for film sets, television series and commercials! For example, some scenes from 'Gladiator' and 'The English Patient' were filmed in Monteriggioni! And the famous saga of vampires in 'Twilight'? Some important scenes of the 'New Moon' were also shot in Montepulciano!

 

  • AROUND AREZZO. This area will reveal some of the best villages in Tuscany often lesser known but not neglected in our precious list! If you find yourself near Arezzo there are three places that you should not miss: the Etruscan Cortona, Anghiari  with its famous Sorci Castle and Poppi, immersed in the green valley of the Casentino.

 

  • AROUND FLORENCE. Rest assured, near Florence, the capital, there are some beautiful medieval Tuscan villages. In particular, we suggest two very interesting and famous small Tuscan villages for being the birthplace of important characters which you surely have heard of. Between Florence and Siena, there’s the birthplace of the poet Giovanni Boccaccio, Certaldo, a village that is also famous for hosting the annual Mercantia, one of the most important festivals of street theatre.

    The famous person connected to the second stage of our suggested itinerary contains in his name a reference to the town that was his birthplace: Leonardo da Vinci. The painter was born, in fact, in the beautiful village of Vinci, which houses the Leonardo Museum and Library dedicated to this great artist.

 

  • AROUND PISA. If you travel from Siena to Pisa take the opportunity to visit Volterra. This small town is one of the most beautiful Tuscan villages and its Etruscan origins have left their mark until the present day. If you instead decide to discover the landscapes of Maremma Pisana and get close to the sea, take a break to enjoy the wonders of Montescudaio, and its Church of Santa Maria Assunta.

 

  • AROUND LUCCA AND PISTOIA. Another one of the small villages in Tuscany, Italy to visit is Collodi. The father of Pinocchio, Carlo Lorenzini, was so fond of this village that he decided to change his surname to this location. This small town in Tuscany to visit is located halfway between Lucca and Pistoia and is home to a beautiful park entirely dedicated to the stories of the beloved puppet.

    North of Lucca, and set in the mountains of the Valley of the Garfagnana is the town of Barga. This beautiful Tuscany small town was liked very much by Pascoli who dedicated the poem 'The hour of Barga' to it: we suggest, between one reading and the other, a visit to the beautiful Cathedral of Saint Christopher!

 

  • AROUND LIVORNO AND GROSSETO. Our journey continues south through the best villages to visit in Tuscany. Near Livorno and near the coast, you should visit the medieval town of Suvereto. Wine lovers will be pleased to know that Livorno is famous for its wine production (in particular 'Val di Cornia Suvereto'!).

    From Grosseto, in the area of Tufo, lies the town of Pitigliano. What to do there? Well, you can visit its beautiful old town, full of narrow streets, offers numerous churches and a Synagogue from the 16th century that testifies to the historical presence of an important Jewish community.

 

After our overview (brief but detailed!) you will realize how difficult it is to choose and classify all of Tuscany’s most beautiful villages. These small Tuscan towns represent the true essence of the region and are linked by stunning squares, medieval buildings, abbeys full of charm and offer the possibility to get in touch with minor traditions and cultures influenced by the different provinces.

The ability to travel through rural and hilly landscapes will leave you with the wonderful memory of an alternative holiday and full of surprises. Whatever time you decide to make a visit to some of the small towns in Tuscany, you will be greeted by the beauty and the traces of history that still exist in these magical places.