The most beautiful villages in Tuscany, Part II

Following the great success of the article dedicated to the most beautiful villages in Tuscany, I’ve decided to make a Part II.

Tuscany, the cradle of the Renaissance, is also a land rich in medieval villages and citadels that are part of a bucolic landscape made of enchanting valleys and scenic hills. Each borgo has its medieval story to tell, a story made of towers, walls, fortresses and narrow streets.

As there are really many surprising and suggestive smaller hill towns in Tuscany, here you’re going to find further special places to visit! Extraordinary medieval villages and fortified towns that rise spectacularly on the wonderful Tuscan hills.

Great scenery, fantastic views, picturesque alleys, lovely squares and medieval buildings… enchanting places not to be missed! Let’s discover some of them 🙂

Best Towns and Villages of Tuscany


We are in the famous Chianti area between Florence and Siena, where lovely hill towns rise here and there amid verdant hills and lush forests. Montefioralle is one of the many charming villages of Chianti, it is very tiny but incredibly beautiful and characteristic in itself. Its stone houses adorned with flowers and its incredibly narrow alleys paved with stone, make it absolutely peculiar! Here is also produced a superb Chianti wine.


Rising at the center of the Elsa valley in the province of Florence, Certaldo is extremely beautiful and suggestive. The dominant color of this little hamlet is the one of the red bricks of its impressive and magnificent medieval buildings. The views from Certaldo are also amazing, especially on the part that looks at the wonderful San Gimignano with its unmistakable towers. Here, the famous Tuscan writer Boccaccio spent the last days of his life.

Bagno Vignoni

Bagno Vignoni is a unique peculiar village in Val d’Orcia, where you find the most suggestive and impressive landscape and hill towns of whole Tuscany.

This is a beautiful and very characteristic place, with fantastic thermal springs and an amazing square with an ancient Renaissance pool at its center and magnificent buildings all around. For its suggestive atmosphere suspended in time, Bagno Vignoni is also one of the most romantic places to stay in Italy.


Rising on a hill top in the province of Grosseto, Sorano is also defined as the Matera of Tuscany for the peculiar characteristics of its wonderful buildings carved directly into the tuff rocks. The same characteristics are also peculiar of the more famous Pitigliano and Sovana, that all together make the so-called the città del tufo.

The village is perched at 379 meters above the sea level on a spectacular cliff overlooking the river Lente. Its suggestive center is a maze of alleys, courtyards, arches, stairs, balconies and cellars dug into the stone.


Very close to Sorano and almost on the border with Lazio, lies another hidden gem of Tuscany, the Etruscan town of Sovana. Its enchanting center developed during the Middle Ages over an Etruscan necropolis, under the control of the Aldobrandeschi family, who built the castle and the Rocca.

The heart of the village is the fabulous Piazza del Pretorio, a peculiar square unique in itself, overlooked by beautiful ancient buildings. Sovana also preserves an ancient gold treasure, that was accidentally discovered here in recent years! Follow the link above to know more!

Don’t miss the Best Towns and Villages of Tuscany – Part I, that covers San Gimignano, Volterra, Cortona, Pitigliano, Pienza, Montalcino, Montepulciano, Monteriggioni, and also has a Map!


  • Marcia Aevermann ha detto:

    I have lived in Vicenza and traveled in Italy to many sites. This April I am traveling back to Italy and will be staying in Livorno for a week. I will be heading to Cinque Terra to explore those villages as I have not previously made it to these towns. I have explored Florence, been to Pisa. What would you recommend as day trips from Livorno for unique travel in Tuscany? Maybe two or three?
    Thank you,

    • elena nacci ha detto:

      Dear Marcia,
      Seems like you really love Italy 🙂
      The Cinque Terre area is one of the most beautiful sights to visit in Italy! the landscape overlooking the sea is amazing.

      Among some great day trips to Livorno, I suggest the lovely medieval village of Castagneto Carducci, accessed via a wonderful cypress lined road, and the beautifl Etruscan town of Volterra more inland. On your way to or back from Volterra you may considr a little detour to the charming hill town of Montecatini Val di Cecina, offering splendid views. I imagine you’ve already visited the fantastic Lucca. While, heading inland in direction of Florence you may pay a visit to the small village of Vinci, birthplace of the great Loenardo da Vinci, and pay a visit to the interesting museum devoted to the genius and his inventions, from there a visit to the stunning Certaldo might be a great idea 🙂

      I remain at your disposal for any further help,
      Enjoy your Sunday,

  • Cathy Brabant ha detto:

    Hi Elaena,
    Loved your description of the small towns in Italy. My husband and I are coming to Italy in late October 2015. We want to spend time in Rome, Florence and Tuscany. We have two weeks. We are not sure how to proceed but threw around the idea of after we arrive grab a car at the airport and drive to Montipulciano (only because we are wine lovers and your picture of it is beautiful!). From there somehow go to Florence and Cinqueterra and then back to Rome for a couple of days.
    We open to suggestions! Thanks Cathy

    • elena nacci ha detto:

      Hi Cathy,
      Happy to hear you like my blog. All of these small towns are incredibly suggestive! There are lots across Tuscany.

      You can decide to visit Florence and the Cinque Terre at the start or towards the end of your trip. I would spend 1 or 2 days in Florence; the Cinque Terre can be reached via train from Florence, they can actually be visited on a day trip from Florence, but the journey is quite long so my suggestion is you spend a night there. In case you’re coming back home from Rome then I’d suggest this plan: 1.Florence and Cinque Terre, 2. Montepulciano and Tuscany, 3. Rome.

      Definitely rent a car in Florence and then start to explore Tuscany. Montepulciano is wonderful and a good base, with many charming places to stay, the same can be said about the near Pienza and all the splendid Val d’Orcia area. To get an idea of how to spend 2 weeks in Tuscany and particularly what to visit from Montepulciano, take a look at this useful post of the blog.

      Take a look and get back to me for any further advice,
      elena from Florence 🙂

  • Rabpk ha detto:

    Hey! We are planning on going to Italy coming April and my main focus is Tuscany. Id like some help with my itinerary. After reading your blog I have fallen in love with all these places.
    We are thinking of one whole day in Rome next day we plan on going to Siena by bus. I believe its going to take 2h 39 minutes (15 euros per person)? We are planning on staying here for 3 days. We will probably reach mid day and would like to explore Siena the first day. The second day we would like to go to valdorcia, pienza, Montalcino and Montepulciano to mt amiata. You you think we can do it all in one day? We would like to stay the night in Siena.
    The next day we would like to go to monteriggioni , san gimignano, Castelnuovo Berardenga and san gusme and back to siena.
    Next we have two options either go to Chianti or go to Florence first. We would be hiring the car from Siena anyways so we can go to Chianti first too right? I plan on booking an AirBnb in Chianti region. which town will you suggest to make as a base. plan on staying in Chianti for two days. Siena to(chianti) greve, Montefioralle
    greve to radda, gaiole,panzano, castellina in two days? and stay in one of these villages/town? Which ones the most beautiful? (I apprciate nature and greenery)
    From these towns id like to go to florence. drop the car.Stay a day in florence and next day for pisa,lucca and stay the night at cinque terre. Spend the day in Cinque terre and at night come back to florence and then go to venice stay two days in venice?
    I think its going to be veryyy hectic. Help me Organise my trip please.

    • elena nacci ha detto:

      Thanks for contacting me 🙂 I’m happy to help you 🙂

      A car is actually recommended to tour Tuscany, especially for exploring the countryside.

      Here are my tips on using Siena a base to explore Tuscany with a list of the best day trips to make from there.

      For discovering the Val d’Orcia and its beautiful hill towns I would recommend 2 days, as you have the car you may consider spending one night there. You might visit both Monteriggioni and San Gimignano when leaving Siena for Chianti. Chianti is a great base for day trips, and among its many villages, I particularly like Castellina in Chianti.

      I second your plan to drop the car in Florence and also all the program after Florence 🙂
      Enjoy your trip,

  • Kate Huet Burns ha detto:

    Buongiorno Elena
    I have loved finding your beautiful Tuscany Chic blog…Thankyou…we are in Tuscany for 5 days in October touring in an Alfa Romeo.
    Before reading your great blogs I had already planned our trip to explore and meander through Tuscany…a base 2 days in Villa Sabolini in Colle Val d’elsa, one night in Villa Sant Urburto near
    Radda and 2 nights based at Casa Bolsinia Monteroni d’Arbia
    You may wish to check these awesome places out
    grazi milli Kate

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