In spite of the freezing cold that is covering Italy during these first days of 2017, we had the desire to take a short break after Christmas celebrations. Instead of getting a plane flying somewhere in Europe, we preferred to organize a three days Tuscany tour between the Val di Chiana and the more famous Val d’Orcia.

Being out of the season, and just after Christmas, we found some attractions, restaurants, and shops closed. This was not a big problem, and we enjoyed this Tuscany tour going back home happy, full of good memories and suggestions to share. 

Fortunately, this kind of tour is ideal for every period of the year. While colors and atmosphere (and the crowd) change with the seasons, the beauty and the unique appeal of these places fortunately remain. So, whenever you come, you can follow this Tuscany tour.

Don’t miss our post about the weather in Tuscany to plan the best period for you to come.

Our Tuscany tour between Val di Chiana and Val d’Orcia

We are talking about one of the most tourist parts of Tuscany, but I have to be honest saying that for me, Nicola, it was the first time in almost every place we passed through (shame on me).
Our trip discovering Val di Chiana and Val d’Orcia started from Versilia, along the northern coast of the region, which is where we live. Anyway, wherever you are based this itinerary across southern-eastern Tuscany is perfect and easy to take. Here is a map with the roads we drove, starting from Arezzo, and the places we visited.

Places we visited during this tour


Piazza Grande in Arezzo at night
Piazza Grande in Arezzo

Arezzo was our first stop and personally, it is the place I enjoyed the most. I have always heard good reviews about the city and now I can confirm them.

The historical center is small, but plenty of things to see that a day could not be enough, especially if you love art and churches. Arezzo is known to be an important gold district, for its antique market (every first Sunday of every month), and to be the set of the famous movie “La vita è Bella” directed and performed by Roberto Benigni

Nevertheless, it is not so touristic. We started our walk from the Piazza Grande with its unique sloping pavement, continuing up to the Basilica of San Francesco to admire the marvelous frescoes by Piero Della Francesca representing the Legend of the True Cross.

After a lovely lunch at a local trattoria, we explored the Romanesque-style church of Santa Maria Della Pieve, the Duomo, and the Church of San Domenico which houses a real crucifix of the 13th century designed by Cimabue. We ended up with a walk at the Fortezza Medicea to enjoy a wonderful red-orange sunset.


The following stop of our Tuscany tour was the renowned Cortona, which is only 40 minutes driving away from Arezzo. The village, of Etruscan origins, lies on top of a hill that overlooks the Val di Chiana and the landscapes of the Umbria region with the Trasimeno Lake. We arrived in the dark just before dinner. Christmas decorations still enlighten the historical center. Walking along the paved Via Nazionale and the main Piazza Della Repubblica was nice and suggestive (even if you could feel a bit of sadness at the end of the holiday).

The morning after, we explored the town. I was curious to see what this village looked like. It became famous with the movie “Under the Tuscan Sun” based on Frances Mayes’ memoir. The main attractions are the Duomo, the cloister of San Francesco, and the Basilica of Santa Margherita.

There are also two interesting museums: the MAEC, the museum of the Etruscan Academy and of the city of Cortona, and the Museo Diocesano. Anyway, the best thing to do is just walk. Climbing the little stairs to reach the upper part of the town, enjoying the atmosphere of a traditional Tuscan hamlet with its pebbly roads and the old little houses made of stones.

Moreover, if you visit the Tuscan countryside outside of the season, my suggestion is to avoid Mondays. Here is our last post about the pros and cons of visiting Tuscany in winter. In Cortona, the museums were closed. Only a few bars and restaurants were open. Even the Duomo and the cloister of San Francesco were closed. That’s a shame, considering that we are talking about a place of worship that should be open all day.  

The thing I love the most in Cortona was the landscape from the street while we descend into the valley with the Dome of the church of Santa Maria Delle Grazie al Calcinaio, and the Val di Chiana as background.

After a quick stop to visit the Tanella di Pitagora, a little tomb dating back to the Hellenic period (2nd-century bc), we left Cortona with the promise of coming back with good weather and a livelier atmosphere. 

Chianciano Terme

Chianciano hot springs in Val di Chiana
Hot Springs in Chianciano Terme

Our Tuscany tour between Val di Chiana and Val d’Orcia went on with a stop in Chianciano Terme. With the cold winter weather, we decided to spend a relaxing day at the Terme. We could not make a better choice. The sun was shining and it was great swimming and basking into the hot water of the outdoor pools while the temperature of the air was about 4°C/39°F.

Chianciano was very famous in Italy for its thermal baths, but today it seems to have lost its charm, it would need a renovation and move with the times. Moreover, the thermal baths we chose were modern, clean, and comfortable, and we had a lovely relaxing time there.

Instead, if you prefer the wild hot springs skipping the equipped wellness centers, here is a list of the free hot springs of Tuscany, which is the richest region of Italy for Terme


The temple of San Biagio in Montepulciano, Val d'Orcia
The temple of San Biagio in Montepulciano

After every bath at the thermae, I usually feel so hungry (don’t you?). A Merenda was the perfect thing we need. On the way to Montepulciano, we stopped at a store selling traditional food and wine. We ordered a delicious Panino with finocchiona (a tasty cold cut with fennel seeds) and fresh pecorino cheese. To drink, a glass of red Vino Nobile di Montepulciano.

We spent the night at a nice Agriturismo, just behind the wonderful Tempio di San Biagio. The location was great at the foot of the village of Montepulciano. Exactly what we were looking for, deep in the countryside. A rural apartment with a garden, barbecue (for the lucky people who come here in summer), the farmer’s granary, tractors, and plows. And a lovely view of the landscape of Val d’Orcia and the village. The following morning, after breakfast there was nothing better than spending a few moments of silence admiring the panorama.

Set 605 meters above sea level between Val di Chiana and Val d’Orcia, Montepulciano is a quite big village compared to the other gems of the area. Of Etruscan origins, the height of Montepulciano’s splendor was during the 16th century under the dynasty of Medici.

Being a car-free village, visitors can leave their car in one of the parking just out of the defensive walls, and walk into the historical center.

There are both pay and display parking within the blue lines, and free spaces within the white lanes).

We started our tour of Montepulciano from the Church of Santa Maria dei Servi and the fortress, at the highest point of the village.

We continued in the Piazza Grande, the heart of the village. The Piazza hosts some of the main attractions of the village like the Duomo and the Palazzo Comunale. It was built with the same style as Palazzo Vecchio in Florence as per Cosimo I Medici’s wishes. Even the historical Palazzo Nobili-Tarugi overlooks the square, just beyond the old well with the Medici Coat of Arms.

The day was not so warm, so we took a break with a hot chocolate in a lovely chocolate lab along the Via Ricci. Then we walked to the lower part where we entered the Church of Santa Lucia and Sant’Agostino.

Before leaving Montepulciano, we had the time to take a free tour of the underground of the town. Beneath three ancient buildings we walked along hidden crypts, chambers, tunnels, and even a “well of love”.

The entrance is inside the small Bottega Ercolani where you can even buy local products and wine.

Montepulciano is also the set of the movie New Moon, the second chapter of the Twilight Saga, and of the recent TV show Medici Masters of Florence.

Consider taking part in a guided tour of a wine cellar in Montepulciano. We are in the birthplace of the excellent red Vino Nobile.


Pienza was the next stop of our itinerary. From Montepulciano, instead of following the Strada Statale 146, we chose to drive along a Strada Bianca (white road), an unpaved countryside road that offers wonderful scenery and panoramas to admire. Many white roads cross the Val d’Orcia connecting the villages. There are a lot of itineraries that bikers can take to explore this fairyland (better with the good weather). If you have time I suggest you also take a look at the little hamlet of Monticchiello di Pienza.

The main Square of Pienza in Val d'orcia
Piazza Pio II in Pienza

Considered the perfect Renaissance town, the historical center of Pienza is UNESCO World Heritage since 1996. The hamlet is lovely, well-preserved, and clean. Due to the winter season and the cold weather, the streets were empty. Only a few tourists like us and almost every shop closed. Wonderful is the main Piazza with the Duomo and the Palazzo Piccolomini (unfortunately closed during wintertime).

Unique is the panorama of the Val d’Orcia you can admire from the Terrazza at the end of the Via del Bacio and Via dell’Amore. Anyway, it didn’t strike me. I find it too much perfect, almost unreal, a restored tiny village made for tourists.

And more expensive than the other towns we visited. A simple soup warmed in a microwave, small water, and a disgusting espresso in an anonymous bar cost us like a two courses menu plus water, wine, and grappa in a traditional trattoria in Arezzo.

As I said about Cortona, I definitely have to come back in spring to enjoy a livelier atmosphere, breathe the good aroma of Pecorino cheese in the air, and visit the Palazzo Piccolomini. 

The Abbey of Monte Uliveto Maggiore

Taking the advice of the owner of the agriturismo, we decided to end our Tuscany tour visiting the Benedectine Abbey of Monte Uliveto Maggiore, nearby the village of Asciano. The Abbey is located in the moon scenery of the Crete Senesi, hidden by a dense group of high cypresses. Honestly, I did not know much about this place. What a big surprise when, after five minutes walking into the cypress grove, the abbey appears.

The abbey was founded by San Bernardo Tolomei. He was a professor of law and a member of one of the most powerful families of Siena during 1300. They built the church between 1400 and 1417 in the Romanesque-Gothic style. Then, during the 18th century, it was turned into a baroque style.

The place I appreciate the most is the cloister where 35 frescoes, representing scenes from St. Benedict’s life, cover the inside walls. Today the abbey has 450 monks that live in seclusion. Visitors also find a cellar and an herbalist’s shop where buying monk homemade products.

The abbey was the last stop of our three days Tuscany tour between Val di Chiana and Val d’Orcia. It was already sunset when, on the way back home, we followed the panoramic Via Cassia. The historical road runs along the crests of the Crete Senesi up to Siena, and we enjoyed very much the marvelous scenery that everyone wishes to see at least once in a lifetime.

Crete Senesi in Val d'Orcia at Sunset
Sunset along the Crete Senesi

Did you find this tour of Tuscany interesting? Leave a comment with your opinion and do not forget to pin it!

Tour of Tuscany in 3 days between val d'Orcia and Valdichiana

27 thoughts on “3 days in Tuscany: Val d’Orcia and Val di Chiana

  1. Jamie says:

    Your photos are stunning! The countryside and architecture is superb. I like the idea of strolling through the car-free village. I’ve pinned this for future reference. Thank you!

    • Nicola - My Travel in Tuscany says:

      Thanks a lot Jamie!! I am happy you liked my pics and the post. If, in the future, you need any kind of information, let me know. 🙂 Car-free villages during the off-season are a sort of paradise for photographers…no people in the streets! 🙂

  2. Sonia Sahni says:

    The place looks so lovely, deviod of the crowds. I would love to be here in off season on shoulder season to truly enjoy the place. I also would love to join an Italian cooking class in Tuscany …I hear they teach you to make the world’s best tiramisu!

    • Nicola - My Travel in Tuscany says:

      Tuscany off the season is great cause you won’t find too many tourists. But you have to better plan your itinerary because not all the attractions and museums are open everyday. Mostly all of Mamma and Grandma prepare tiramisù…you could learn their secrets to make the best tiramisù ever. 🙂

    • Nicola - My Travel in Tuscany says:

      Hi Paulina, thanks for reading and for the comment. Next time you come to Italy you have to stop between Northern and Rome, and visit us. Concerning food, we had great traditional food (especially in Arezzo and Cortona) during those days without paying too much. Depending on where you are you can taste different specialties that you won’t find elsewhere 🙂

  3. Tweet E says:

    It sounds like you got a great deal done in just 3 days. Tuscany has been on my bucket list for years. After seeing this I think that I might be able to make swing through the city while in the country visiting other places. Thanks so much for the great pics all these places look like they’re right out of a movie!

    • Nicola says:

      Thanks a lot Tweet E. Traveling in Tuscany you can do a good mix of cities of historical importance, and beautiful countrysides. Without forgetting the seaside. 🙂

    • Nicola says:

      Dear Chloé, thanks for reading. Happy you find the post interesting, and I hope it will be helpful whenever you come to Tuscany. 🙂

  4. Marissa Abao says:

    This tour was awesome! After I have watched the ‘Under the Tuscan Sun’ a few years ago, I have added Tuscany on my bucket list. The place is just perfect.

    Iza c/o Kathy James (Walk About Wanderer)

    • Nicola says:

      In Cortona you can even walk a little away from the town and reach the lovely house were the movie was filmed. 🙂

  5. Nicole Anderson says:

    I notice you mentioned Under the Tuscan Sun film – and even though this is one of my very favorite movies – I have wanted to travel to experience Tuscany well before I saw the film. Everything that I have read or seen has shown this to be a wonderful place, full of beautiful culture and warm, genuine people. Your lovely post has again confirmed this and I really did enjoy reading it so much. I will get there for myself one day!

    • Nicola says:

      Cortona, became famous worldwide thanks to that movie…I am happy you enjoyed the reading and thanks for consider us warm and genuine. 🙂 I hope one day to welcome you in Tuscany. 🙂

  6. Ling Ge says:

    Wow, you really saw a lot in just three days! We’ve always talked about visiting Tuscany the next time in Italy, and we’ll keep in mind about which season to visit (we had that same experience in France). Love your photos of the architecture there. We loved the show Medici: Masters of Florence, so it’s great to know where the site of the show is. When we get there, I’ll keep your post in mind and hopefully see some of the places you didn’t get to see as well.

    • Nicola says:

      Hello Ling. Having only three days, two nights, we did not stop in every place for so long. Of course the same itinerary can be done in a more relaxing way, especially in spring when days are longer. We enjoyed the Medici TV show as well, and was nice to see with my eyes the places where they filmed it. Last summer we were some of the first websites to write something about the show:

  7. Tatum Skipper says:

    Italy is it’s own world in itself; so magical! When I was there I only explored Tuscany for one day and that was only some of the vineyards (still amazing!) Those thermal baths look so cozy and relaxing after a cold day walking around. I must go back and explore more!!!

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