Tuscany is such an extraordinary and varied land of Italy, and with so many different sights and attractions spread all across its territory, that one gets continuously surprised by new hidden corners. Even for people living here like me, Tuscany is a continuous discovery.

Tuscany off the beaten path

Beyond the most touristic Tuscan destinations, such as major art towns and Tuscany popular medieval hill villages like Volterra or San Gimignano, there’s much more to discover.

There’s also a lesser known and unusual part of Tuscany, equally fascinating and incredibly amazing; made of tiny hamlets and picturesque villages rich in history, old traditions, peculiar crafts, ancient walls, lovely alleys and stunning landscapes.

Uncommon places, that right for this, are extraordinary and have the great pleasure of new unexpected discoveries.

Here you can find new unconventional routes in Tuscany through small medieval and Renaissance villages remained intact all over the centuries, which preserve the charm of narrow streets and alleyways winding through enchanting historic buildings.

As there are so many extraordinary places in Tuscany that are off the beaten path, I’m going to split this post into two parts. Stay tuned for part II 🙂

Tuscany off the beaten path, lesser known hill towns

1. Anghiari

Rising on a panoramic hill in the beautiful countryside of Arezzo, Anghiari is a real gem of Tuscany! Its small historic center, made of stepped alleyways, gives it an incredibly suggestive atmosphere, not to mention its fine views.

During the famous battle of Anghiari, in the year 1440, the Florentines defeated the Milanese army of Filippo Maria Visconti. The Battle of Anghiari was the subject of one of the most famous and discussed lost masterpieces of Leonardo da Vinci, the Renaissance fresco that should be hidden in Florence’s Palazzo Vecchio, behind the fresco by Giorgio Vasari.

2. Collodi

Collodi is a lovely and peculiar small hill town east of Lucca. Its name soon brings to mind Pinocchio, the famous children’s book by Carlo Lorenzini, alias Carlo Collodi, that used the pen name of Collodi in honour of this small village, birthplace of his mother.

The Parco di Pinocchio is dedicated to this famous tale, it’s very interesting, especially if you have children. Villa Gargonzi, located at the bottom of the town, that scenically develops vertically on the mountain’s slope, is impressive! not to mention his beautiful and magnificent garden.

3. Montefioralle


Maybe the most characteristic and ancient hill town in Chianti, Montefioralle seems to get out of a painting, with its stone houses standing side by side, its little balconies adorned with flowers and its medieval walls. A fine Chianti wine is produced in the area.

4. San Casciano dei Bagni


This wonderful thermal village in the province of Siena is surrounded by a beautiful scenic countryside; all green hills, cypress trees, and lush forests. Its town center is typically medieval with a twist of narrow alleys and lovely squares.

San Casciano dei Bagni is one of the best thermal destination in Tuscany, do go for the Fonteverde Tuscan Resort & Spa for a super stay in a unique environment!

5. Murlo


Murlo is an extremely appealing tiny medieval hill town south of Siena, its ring of houses forms thick walls, enclosing the town center with the town hall and the church. Its Etruscan Museum is not to be missed.

6. Santa Fiora


Santa Fiora is a peculiar l village on the Monte Amiata, south of Siena. The Aldobrandeschi clock tower facing Piazza Garibaldi is lovely, as is the square. Particularly impressive is the Peschiera – fishpond, rising around the springs of the river Fiora and surrounded by a wall with a wonderful garden surrounded by woodlands and brooks. It was commissioned by the Sforza family in the sixteenth century.

7. Certaldo Alto


Certaldo is a striking medieval hill-top town in the heart of the Elsa valley, with red-brick towers, palaces and battlements and enjoying enchanting views over San Gimignano and its towers. Certaldo is known for its connection with the famous Tuscan writer Boccaccio; here you can visit the house where he spent the last years of his life.

8. Poppi

Set in the beautiful province of Arezzo dominating the Casentino valley, Poppi is a very tiny village and one of the most stunning hill towns of Tuscany. Poppi is dominated by the Castle dei Conti Guidi, impressive castle with a beautifully frescoed chapel.

The landscape surrounding the village is of exceptional beauty.

 9. Radicofani


Rising south of Siena near the Monte Amiata, Radicofani is a small charming hamlet dominated by a spectacular medieval fortress. The panorama from the top of the rocca is something that takes your breath away! During the Middle Ages the fortress also had its Italian Robin Hood!

10. Pitigliano

Though more famous and well known than the previous destinations, Pitigliano is often left out from the common tour of Tuscany, also due to its location at the far end of Tuscany on the border with Lazio.

Pitigliano, also known as the little Jerusalem, is a real treasure of Tuscany, an exceptional and unique sight! It rises from the rocks and seems to be suspended up in the air. Its houses seem to be part of the rock itself and its town center is exceptionally astonishing! Narrow streets, arches, Etruscan tombs, wells, and cellars. The green landscape surrounding the village is then fabulous! Sorano, Sovana, and Pitigliano are known as the Città del Tufo, as they are carved into the tuff stone in a unique territory with countless remains of ancient civilizations, such as the Etruscan necropolis along the Vie Cave.

This is just a little personal selection of the endless sights and hill towns in Tuscany that are less popular but incredibly worth your visit! 🙂

Which other hill town would you add to the list? More hidden Tuscan hill top towns to discover? Go to our Part II! Suggestive Tuscan hill towns off the beaten path, Part II


  • Allen ha detto:


    Thank you very much for investing so much enthusiasm (and time!) in sharing information on lesser-known / less-visited places in Tuscany. Allen in the U.S.

    • elena nacci ha detto:

      Dear Allen,
      thanks a lot for your message 🙂
      I’m happy you like my post.
      Have a nice day,
      elena from Florence

  • Martha ha detto:


    I was lucky enough to have spent a month in the hill town of Anghiari! Not enough adjectives to describe my tiime there. If anyone is thinking about visiting Tuscany this town should be considered!!

    • elena nacci ha detto:

      Dear Martha,
      You’re so right! Anghiari is a very beautiful and suggestive town. If you like to tell more about your holiday on Tuscany, do not hesitate to come back here and see your story published in this special section of the blog.
      Have a nice weekend,

  • Sara ha detto:

    Hello Elena!

    We are looking for an intact village with train acces to Florence. Thank you for your advice.

    • elena nacci ha detto:

      Dear Sara, here I’m am finally 🙂 thanks a lot for your comment! Among the most beautiful and intact villages with train access to Florence, you may consider the fascinating and panoramic Cortona, and also the beautiful Arezzo or the amazing medieval Siena. Another real jewel with train access to Florence is Montepulciano, follow the links to see these unique destinations in Tuscany:-) For any other tip just contact me again, elena

  • Noel Mackenzie ha detto:

    A very useful article describing the beautiful and historic villages of Tuscany. My wife and I are planning a two- week trip to Tuscany in early October this year and we were struggling to get good information on places to visit where one can enjoy smaller more quaint places rather than the big cities and towns. Your article was brilliant.Thank you.

    • elena nacci ha detto:

      So happy you found my article about these lovely and lesser known Tuscan villages so helpful! Thank you so much! and get back to me telling about your visit to Tuscany ❤️

  • Marc Deutscher ha detto:

    Hi Elena,

    Thank you for this very helpful information. I will be traveling with my 15 year old son this summer and we will be driving from Rome to Siena and then from Siena to Scandicci in one day and then from Scandicci to Pisa and from Pisa to Florence back to Scandicci on the next day, then Scandicci to Florence spending the full day there and finally leaving Tuscany driving from Scandicci to Venice. I am trying to plan the most beautiful routes with some amazing stops along the drives. If you can help us narrow down the very best not to be missed places I would greatly appreciate it. I know that we can’t see everything and I also know trying do this trip with a teenager can be trying in and of itself.
    Thanks for your help.

    Marc D from NYC

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