Tuscany: the Valdichiana Senese trail

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

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.

Not 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.

Chiusi

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.  

Cetona

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. 

Sarteano

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.

Apart 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.

Castelmuzio 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!    

Trequanda

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.

The 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.

USEFUL TIPS

• 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,