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Tuscany: the Valdichiana Senese trail

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The Valdichiana Senese is a stunning stretch of Tuscan countryside known for its Vino Nobile di Montepulciano and top thermal centers.


Valdichiana Senese is a stunning stretch of beautiful Tuscan countryside where you’ll find pretty hamlets, producers of Vino Nobile di Montepulciano and some of the most renowned thermal centers in the region.


A short drive south of the lush vineyards of Chianti and the elegant towns of San Gimignano and Siena brings you to Valdichiana Senese, a corner of Tuscany that truly looks like a painting. Its luxuriant green hills and yellow wheat fields lead from one pretty village to the next and fill your eyes with the beautiful shades of the Tuscan countryside. It’s the ideal choice for those seeking a holiday in a peaceful and scenic location.

Here’s a little itinerary to explore the Valdichiana Senese. It starts from Montepulciano and brings you through less-traveled villages immersed in the pristine countryside


Montepulciano is the main municipality in Valdichiana Senese and it’s a true architectural gem steeped in history, culture, and tradition. From the imposing Porta al Prato, the northern city gate, you can walk uphill to Piazza Grande, the main square and the highest point in town. This iconic piazza (Twilight fans, this is where Bella saves Edward from the Volturi in New Moon…) is dominated by the Gothic façade of the Palazzo Comunale and lined with stunning historic buildings.

Tuscany-valdichiana-senese-montepulcianoNot to miss are the XVII-century Cathedral of Santa Maria Assunta, with masterpieces from the Sienese school, the Town Hall, where you can climb to the top of the tower to enjoy beautiful views, and the Church of St. Augustin, with a pretty white stone façade and a beautiful array of artworks inside. Oh, and of course you can’t leave Montepulciano without a glass (or two) of Vino Nobile, the high-quality red wine produced here.


About 25 km south of Montepulciano you’ll find Chiusi, a charming town perched on a hill at the border between Tuscany and Umbria. This place dates back to 1000 BC and was once a key settlement of the Etruscan empire. Definitely a must-see for archeology lovers, who will be amazed by the fantastic findings on display at the National Etruscan Museum, one of the most important collections of Etruscan remains in Italy.

If you’re not really into ancient history, I’m sure you’ll enjoy exploring the vast network of tunnels and passageways stretching underneath the village, known as Porsenna’s Labyrinth, from the name of the legendary Etruscan king of Chiusi. Also, just 4 km from the old town center is the pretty Chiusi lake, where you can immerse in nature and enjoy some bird-watching.  


A short drive from Chiusi leads to Cetona, a quintessential Tuscan village located at the foot of the homonymous mountain. Here it’s all about charming paved streets, stunning villas and beautiful panoramic spots (check out the views from via dello Steccato…).

Things to see in Cetona include the XI century Church of San Michele Arcangelo, the frescoes by Pinturicchio in the Collegiata of Santissima Trinità and the Belvedere Archeological Park with caves that were once used as places of worship and burial. Another interesting site is the monastery founded by Saint Francis of Assisi in 1212, where you can explore the grounds and then dive into a unique (but expensive) dining experience at La Frateria


Next stop is Sarteano, a tiny, yet very lively, village dominated by a massive XI-century castle. Despite its small size, there are lots of interesting sights to explore here, including the stunning medieval loggia in the central square, the magnificent XVII-century Arriscianti Theater, the Church of St. Martin in the Forum with its extraordinary works of art, and the historic Bologni pharmacy displaying herbals, antique ceramic, and glass jars.

Sarteano is also home to one of the most beautiful Etruscan tombs in Tuscany, the IV-century Tomb of the Infernal Quadriga. In this delightful Tuscan hamlet, you’ll also find renowned thermal baths where water flows naturally at 24°C!  

Chianciano Terme

Time to hit the spa! Just a short drive north of Sarteano, Chianciano Terme is a popular spa town whose healing thermal waters have been well known since Etruscan times. Surrounded by century-old oak trees and olive groves, this is a place of beauty and relaxation that can easily be used as a base for exploring the treasures of Valdichiana.

Tuscany-valdichiana-senese-chianciano-termeApart from its spa parks, Chianciano features a pretty old town with some interesting sights, such as the works of art on display at the Collegiate Museum of San Giovanni Battista, the Archaeological Museum inside a former granary and the medieval Clock Tower with great views over the surrounding countryside.

Montisi and Castelmuzio

Driving further north through lush green hills and wheat fields, you’ll reach two picturesque villages you probably haven’t heard of before: Montisi and Castelmuzio. Montisi is a vibrant hilltop village adorned with the colorful flags of its four contrade (districts). It features one of the world’s smallest functioning theatres and the famous Piccolo Accademia conservatory which draws harpsichord teachers and students from all over the globe.

Tuscany-valdichiana-senese-montisiCastelmuzio is an enchanting hamlet of 200 souls with one of the most beautiful panoramic terraces I’ve ever seen! Far from the glamorous Tuscan resorts you often see in magazines, this is a totally untouristy corner of Tuscany, with just a bunch of sloping streets, a bar/restaurant, and a tiny supermarket. It’s so peaceful here that the only ‘noises’ you’ll hear are birds chirping and bell ringing from the church!    


I suggest to visit Trequanda at dusk and head straight to Conte Matto restaurant to dine on the fantastic terrace overlooking the valley. Weather permitting, it’s truly an unforgettable experience! Trequanda is another Tuscan gem where life is centered around the piazza.

Tuscany-valdichiana-senese-trequandaThe entrance to the village is still partially guarded by the remnants of the ancient Cacciaconti Castle, with an imposing cylindrical tower. There is also an interesting Romanesque church boasting a unique brown-and-white-checkered façade.


  • For this trip, I stayed at Casa di Castello, a fantastic holiday home in Castelmuzio with the most welcoming hosts
  • Food and wine are an essential part of every trip to Italy and here in Valdichiana you shouldn’t miss pici, Tuscan-style hand-rolled pasta served either all’aglione (a garlic and tomato sauce) or with wild boar ragù sauce, pecorino cheese, and Chianina meat, all washed down with some good Vino Nobile di Montepulciano red wine
  • Restaurants I can recommend in this area are Conte Matto in Trequanda, Locanda di Casal Mustia  in Castelmuzio and Da Roberto in Montisi

Until next time,

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35 thoughts on “Tuscany: the Valdichiana Senese trail”

  1. Tuscany is so beautiful. It’s been on my list since long and I always wanted to visit it. This post is really useful And will keep it handy when I book my holiday here.

  2. I would love to visiti Tuscany one day. Get a gorgoues little villa with a pool in the summer. I had no idea there were so many little small towns to explore and there was so much to do. And yes…. I’d be drinking and eating absolutely all day.

  3. Tuscany is home to some of the cutest Italian towns and villages and you’ve done a great job by putting together a list of some of the best ones! I especially love Cetona (I have not been there but from the pictures, I mean). Chianciano Terme also looks pretty cool and the fact that its a spa town adds to its appeal!

  4. Tuscany is so beautiful! I have been several times and your post makes me want to go back there so badly!!!

  5. I always love reading post about new places 😉 Your photos have perfectly captured the beauty of the Tuscany ! These photos definitely make me want to book a trip right now to Italy. It’s not easy to pick just a few places when you consider that Tuscany is full of wonderful hidden gems, especially when considering that “beauty” is subjective and depends on what you are looking for. Thanks for sharing your travel experience !

  6. Thank you for this compiled list! I’ve always wanted to take a Tuscany trip that explores the smaller towns, but have gotten a little overwhelmed trying to decide or do research. Can’t decide which one I’d like to visit most!

  7. I love this list. I have never explored Tuscany but this post is giving me some good ideas. Montepulciano, Cetona and Chianciano Terme look very nice. But I wonder how easy it would be to get there for someone who doesn’t drive.

  8. I love Tuscany, and I’ve stayed in Montepulciano two times over the years. I have not been to Trequanda, Montisi, or Castelmuzio — and they are now on my list for my next road trip there. I love the more quiet, unvisited towns in Tuscany, and these look PERFECT. Thanks for sharing!

  9. I’m not sure I’d say I’m an archeology fanatic, but I just think it’s so cool standing on the same ground where you know people lived and stood all the way back to 1000BC! Chiusi would definitely be on my list for that reason alone. Honestly I’d love to visit all of these places. They just look so quaint and picturesque.

  10. You’ve given me some great ideas for my next European/TUSCAN roadtrip. Let’s hope that I can get around to that soon, because I’m generally always missing Italia and it’s been too long since I’ve had an Italian Summer. Cheers!!

  11. Before reading your posts, I never knew the names of these stunning Tuscan towns. They are amazing with those narrow streets and old architecture. Though, I visited Florence but did not visit these beautiful, quirky towns. I loved pictures of Cetona and Montisi the most.

  12. This looks incredible! I would love to travel each and every one of these small villages, as they look so picturesque, simply adorable! I will bookmark this for future reference. if the travel gods are with me, I will get there sooner, rather than later. Thank you for such an amazing post!

  13. Who doesn’t love Tuscany– esp in the summer… this has me wanting to book a trip back it italy asap!! 🙂

  14. Wow! These little villages look incredibly beautiful. I love their rustic architecture, cobblestone streets and narrow alleys. Although they all look so picturesque and it’s quite difficult to choose the best, Montisi and Castelmuzio would be my favourites. Thanks for sharing the amazing photographs and useful tips.


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