Tuscany and nature: a tour of Crete Senesi, Val D’Orcia and Val di Chiana

If you have 2 or 3 days and you wish to elevate your soul up to a state of peace of mind, then the tour of Crete Senesi, Val D’Orcia and Val di Chiana is what you need! You’ll be simply amazed by the colours, smell and sounds of nature in this spot of land, which matches nature, culture and traditions.

Our opinion is you’d better do something like a “Fly & Drive” rather than staying for days in the same town: the medieval towns you come across are really nice and they definitely deserve to be seen but half a day to visit each place is more than enough, because they are quite small and you can visit them quickly.The towns themselves are open-air museums, so even by having a walk around, you’ll be satisfied!

Val d’Orcia is famous for its rolling hills and especially during spring, it seems that you may jump over dozens of green mattresses! It is included in the province of Siena and partly in the province of Grosseto. The main towns of Val D’Orcia are Castiglione d’Orcia, Montalcino, Pienza, Radicofani, and San Quirico d’Orcia.

Crete Senesi refers to an area in the south of Siena and it is characterized by a landscape that is often described as lunar: the greysh colour of the soil and its gullies make this land appear as a place where time has stopped. The main towns of Crete Senesi are Asciano, Buonconvento, Trequanda, Monteroni d’Arbia, Rapolano Terme and San Giovanni d’Asso.

Val di Chiana is a very wide area that stretches between the provinces of Arezzo and Siena but it is also including a part of the province of Terni in region Umbria. It is characterized by a landscape rich of vineyards but also of lovely Medieval villages and the main towns included in the area are Arezzo, Castiglion Fiorentino, Cortona, Foiano della Chiana, Lucignano, Monte San Savino, Cetona, Montepulciano, Chianciano Terme, San Casciano dei Bagni and many others.

Said this, we suggest you to choose one place to sleep (for example we decided to stay in a very nice B&B in Lucignano) and drive around. After all, the most interesting towns and attractions are at your fingertips, being about 30 minutes drive from each other. We suggest a couple of options: if you have 2 days, maybe you’d better concentrate on one area and visit it in detail. If you have 3 or more days, you can make a complete tour of Crete Senesi, Val D’Orcia, Val di Chiana and their towns.

We had 3 days available and we decided for a complete tour: obviously we didn’t have time to visit all the towns, but we made a good selection of the most interesting ones and we are glad to share our experience with you and hope you can find it useful.

Coming from region Marche, for our convenience we went for a “round trip”. So, we decided to start from Crete Senesi, also because everybody knows and praise other most popular areas in Tuscany, but just a few know how magic and surreal Crete Senesi can be! Creta means “Clay”, which is the main material, that characterizes this spot of land: gullies and hills of clay appare here in there and the tyical grey/beige colour of the land gives the landscape an appearance often described as lunar! During spring this magic landscape alternates with “soft”, green rolling hills and rows of cypress trees pop up here and there.

The first town we visited in the area of Crete Senesi was Trequanda, because we heard it was a lovely town and we can confirm it! It is very small but well kept. Trequanda is placed on a hill, completely surrounded by thick woods, tidy vineyards and olive groves, in one of the best preserved areas in the territory of Siena. What is really attracting for us about this town is that mass tourism hasn’t spoilt it: you can see it because there are not so many souvenir shops, but only what is necessary to live and because all the buildings are well kept, but not restored to forcedly attract the eye of the tourist. Trequanda is very real! So this could be an ideal place where to live: quiet, with all services, clean and close to many interesting places. Worth a look in Trequanda: the two medieval doors (Porta a Sole and Porta a Leccio) of the ancient defensive circuit and the Castle, built in the XIII century, characterized by the typical battlements, a cylindrical tower and a beautiful Italian garden. Just a few steps from the castle, there is the Church of Saints Peter and Andrew, built in 1327 in the Romanesque style and famous because inside there are interesting works by Sansovino. The facade has a two-coloured chessboard pattern, obtained by alternating tufo and travertine stones. In front of the church, there is a street sloping down and leading to a very nice belvedere, where there is a bench where you can seat and contemplate the breathtaking view or take some unique pictures! As for the rest, just enjoy a walk around and try to imagine how life during medieval times should have been!

The second stop was by Asciano, which is considered the main town in the area of Crete Senesi, being in the center of this magic spot of land. To be honest, Asciano is much less interesting than other towns in the surroundings because modern architecture has spoilt a little bit the look of the town but if you are in the surroundungs, it may be worth a short visit.

The most interesting monument to see in Asciano is probably the XI century Romanesque Basilica of Sant’Agata, which was built with travertine marble. The church, is characterized by a nave with cross vaults and it is adorned with decorative elements in Lombard style. Outside you can admire its 13th century bell tower. The interior houses two XVI century frescoes, one by Il Sodoma and a Pietà probably from Bartolomeo Neroni. In general, the look of the church is very simple and plain, but it is typical of the Romanesque style and it conveys a sense of grandeur.

As for the rest you can have a walk along the main street of the old town of Asciano and its alleys. You’ll see that they are investing in the good restoration of many buildings. Hopefully, it will be brought back to its original splendour, in the typical senese style.

Anyway, whether you decide to visit Asciano or not, have a drive around the area, because you can enjoy some amongst the most magnificent landscapes in Crete Senesi, where gullies are stuck in front of you, showing all their grandeur and magnificence.

From Asciano, you may drive down to lovely Buonconvento: it wasn’t included in our plans, but when we passed in front of it to reach our destination, we couldn’t help stopping by! The look from outside is more like a huge villa with enclosure walls, rather than a town: indeed, what you can see from outside is the circuit of strong defense walls, whose architectural style recalls the one of Siena.

Inside the walls, the village is crossed from north to south by Via Soccini, where you can find, first of all Palazzo Podestarile, with the XIV century rectangular civic tower and the two Gothic arches in the façade, which has 25 stone coats of arms of the old podestas. The construction of the building and the tower was ordered by the Sienese Governors. It was initially the Vicari residence and of the Podestà after 1410.

After that you come across Palazzo Comunale (the Town Hall) with its attractive brick front, and the imposing Palazzo Taja, built entirely in brick in the second half of the 1700s by a noble family. On the southern side the façade is enlivened with a large balcony with a wrought iron railing and a sundial above.

Walking further you can find Palazzo Borghesi, built in the XIV century, which belonged to an old Sienese family whose coat of arms can be seen on the wonderful façade.

Nearby is Palazzo del Glorione and in front of it there is the Church of Saints Pietro and Paolo, which also has a fine brick façade. Its current classical style is the result of a restoration work in the 1700s. A small marble stone bearing a cross and inserted in the wall to the left of the façade is engraved with the date 1103, which could be the date of its founding.

There are two other important streets in the old town: one on the east side called Via del Sole (“Sun Street”), and the other one on the western side called Via Oscura (“Dark Street”), both communicating with Via Soccini and paved with stone slabs. The buildings on Via del Sole are more modest, and until the 1930s they were lived in by families of carriers, carters, people who transported goods. The initial stretch of Via Oscura has many overpasses with intermittent tunnel arches that create an atmosphere of light and shade. This area is called “chiasso buio” and is the most characteristic neighborhood, with part of the street paved with medieval cobblestones. They may be so called because, while Via Del Sole is quite sunny, Via Oscura is characterized by arches and vaults, creating a chiaroscuro effect.

Just a curious detail: the name Buonconvento derives from Latin Bonus Conventus, which means “happy, fortunate community”. How could you not see a happy place?!

Last but not least: Buonconvento is officially listed amongst the most beautiful Medieval villages of Italy and we do not wonder why!

Once said goodbye to the Happy Town, you can drive south to San Quirico D’Orcia. Now you are officially in Val d’Orcia, a UNESCO Heritage World Site since 2004. Have you ever seen that “magic” picture, probably the most representative of region Tuscany, with a house on top of a hill and a long path of cypresses? Yes, that’s the place! The countryside around San Quirico is amazing and it will leave you breathless, no doubt, any time of the year. Photographers from all over the world come over to take beautiful pictures of the landscape: they are good photographers, for sure, but… taking pics in Val D’Orcia is like portraing Gisele Bundchen instead of the witch in the Snow White fairy tale! Someone would ask: “You like an easy win, don’t you?”

Anyway, San Quirico is characterized not only by a beautiful countryside but also by interesting architecture and history: the town has grown up on the site of the medieval village of Osenna; in 1256 it became part of Siena’s territory and today it still preserves its original street plan. In the town center, encircled by fortified walls, a stop should be made at the Collegiata dei Santi Quirico e Giulitta, with its magnificent Romanesque-Gothic door, as well as at the Misericordia and Santa Maria di Vitaleta churches.

Horti Leonini gardens represent a beautiful example of Giardini all’Italiana: they were designed in the 1540s by Diomede Leoni and from time to time, sculpture exhibition take place in this evocative place.

A final stop should be made by small but very characteristic church of Santa Maria Assunta, dating back to the XII century. The church has a plain rectangular plan with a wall covering in square stones. The apse is crowned with corbels and decorated with suspended arches. Probably the most spectacular part of this extremely plain church is the massive portal, embellished with decorations. Right behind the church, there is the rose garden, where you can romanticly sit for some time in the shade.

San Quirico D’Orcia has been totally and carefully restored, without spoiling, but preserving the original structures, so it will be a pleasure to walk along its streets, sit outside having an espresso and feel one with the town.

While leaving San Quirico, you could stop by the so called Boschetto dei Cipressi (Little wood of cypresses): it is another typical image of Val D’Orcia and Tuscany in general and a very good place to take some beautful pictures, especially at dawn, when the sky turns from blue to red emphasizing the colours of the hills and the contrast with the little wood of cypresses!

From San Quirico D’Orcia we decided to drive to Lucignano first and then to Cortona, being on our way back to region Marche. Both these towns are part of Val Di Chiana: Medieval Val Di Chiana is still evident, albeit reshaped and reinterpreted by the inescapable passing of time, in its stones, scenery and myth. Testimony are castles, churches and fortresses spread here and there.

Lucignano is located on top of a hill, and with its distinctive elliptical shape with concentric ring roads, the fortified village of Lucignano is one of the most interesting examples of medieval town planning. Walking along the streets you will have the feeling of a nice game through an intricate maze that is resolved once you finally arrive in the upper area of the town, where you can find the most interesting monuments of Lucignano, including Palazzo Pretorio (now the Town Hall), the Church of St. Francesco, and the Collegiata.

Palazzo Pretorio is standing right beside the monumental complex of San Francesco. The main facade opens onto Piazza del Tribunale and has many coat of arms and memorial stones with symbols of the various families, that had the power over the years. Probably it was built at the end of the 1200s, and many changes occured over the years. In the 1800s the Milanese painter and sculptor Luigi Ademollo painted some rooms. The building has a basement, once used as a prison, as evidenced by written inscriptions and graffiti on the walls.

Beside Palazzo Pretorio, you can see the church of San Francesco, which is one of the most important examples of the Franciscan Gothic architecture. The construction was probably begun in 1248 and finished in 1289. The facade, high and bright, is made of blocks of sandstone and travertine stone; in the center is placed a travertine portal surmounted by a large rose window. Inside the church there are altars in stone and in wood painted with gold (ranging from the sixteenth to the eighteenth century). The church, originally fully painted, still retains some fragments of frescoes depicting the stories of St. Francesco. Particularly charming and appealing is the great fresco above the first altar on the right wall of the nave, known as “The Triumph of Death,” which shows the precariousness of human life.

The church of the Collegiata is located on top of the town center with its façade overlooking an ellipsoidal scale, connected to a long ramp from Via Rosini and Piazza delle Logge. The Church of the Collegiata stands on the site where once stood the church of St. Michele Arcangelo and a large building, comprising a tower. Of this construction, which was the ancient fortress, the chronicles tell us that it was used as a gunpowder, weapons and supplies depot,. The church is characterized by a Latin cross plan and at the center of its façade opens a majestic door. At the foot of the façade, the beautiful travertine staircase represents the design of the ellipsoid urban structure of the town.

A chronicle from the 1371, states that the towers of Lucignano were built by the Sienesi. As a matter of fact, in 1370 Lucignano subdued the city of Siena. The 3 main doors of the town are: Porta S. Giovanni, Porta S. Giusto and Porta Murata (bricklayered door), so named probably after its closure in the 1500s. The remains of the round towers you can see on the wall circuit are probably dating back to the 1400s.

As for the rest, you can enjoy a relaxing walk along the streets of this quiet, lovely town, that has recently gained the Orange Flag as one of the most beautiful medieval villages in Italy.

From Lucignano, we decided to end our brief Tuscan tour in Cortona, the town of arts, history and culture. Here you will see a totally different environment: tourists crowd Cortona all year around; the streets are full of fashionable art and antique shops; people wearing their designer clothes are having an aperitive in a classy bar, while waiting for the latest exclusive event. After all, Cortona itself, from its dominating position 500 metres above the sea level, seems to be saying “hey, Val di Chiana, I am the sovereign and I hold the very best!”

The town is entirely surrounded by Etruscan walls and fortifications, constituting an important archaeological element as well as one of its most beautiful features. Most of the buildings and streets in town date back to Medieval times and still hold the same charme, thanks to the careful renovation carried out. The only horizontally-running street in Cortona is Via Nazionale, leading straight to Piazza della Repubblica where you’ll be able to admire the imposing Palazzo Comunale, a Medieval building, built in the XII century, on the ruins of a Roman forum. The access to the building is through a magnificent staircase and during sunny days it’s nice just sitting on the steps, looking at passers by to observe how people enjoy this lovely town! Inside the Town Hall there is the Council Hall, with a stone fireplace from Cristofanello dating back to the XVI century.

From Piazza della Repubblica you can easily reach Piazza Signorelli, where Palazzo Casali stands. It is one of the oldest civic buildings of Cortona, also known as Palazzo Pretorio (Praetorian Palace), for having hosted the Florentine commissioners at the end of the Middle Ages. Today it houses the Museum of Etruscan Academy, where a very interesting collection of Etruscan and Roman artefacts are preserved. The architecture dates back to the XIII century and up to the XV century it was inhabited by the Casali family, an aristocratic family of Cortona. Some coats of arms, still visible, are indicating instead the following power of the Florentine commissioners. The facade of Palazzo Casali shows an XVIII century style, a result of the renovations that took place in this century.

On the same square, you can also admire Teatro Signorelli, built in the XVII century. The style adopted by the designer, Carlo Gatteschi, follows the neoclassical trend of that time. When the theater was completed in 1857, it was called Imperial Theatre or Leopold Royal Theatre in honor of the Grand Duke Leopold of Tuscany. Externally Teatro Signorelli shows a long porch with seven arcate. Through the lobby of the theatre, you can reach the horseshoe shaped hall, where the shows are held. If you are fond of theater and you have a free evening, check out the calendar, because Teatro Signorelli always offers a rich theatre season starring great actors and well known companies, that enrich the cultural life of the city. Tickets can be purchased directly from the theater. For the schedule of events or for more info, you can visit http://www.teatrosignorelli.it/ : it is in Italian, but google translator may be helpful. On the other hand you can ask us!

From Piazza Signorelli, with a 150 mts walk along Via Casali, you can easily reach Piazza Duomo, where the Duomo of Cortona (also known as the Cathedral of Santa Maria Assunta) stands. The original church dates back to the XI century and it was built on the ruins of a pagan temple, but only at the beginning of the XIV century it finally got the title of cathedral. Despite the prevalent Renaissance style, due to subsequent renovations, the church shows medieval details and some Romanesque features The Cathedral is divided into three naves, separated by a series of columns and capitals. The barrel vault that dominates the interior dates back to the XVIII century and shows some XIX century decorations. Inside the cathedral is preserved a rich historical and artistic heritage: The Adoration of the Shepherds by Pietro da Cortona, above the altar Capulli and The Descent of the Holy Spirit Tommaso Bernabei. Inside the Duomo, in the right nave, it is also possible to admire the pipe organ, built in the XIX century.

Right in front of the Duomo, you can find the Diocesan Museum, which is divided into nine exhibition rooms, where works of art dating from the II century A.C. to modern art are shown. They come from the churches of the city and from the Duomo itself. A must see is the Painted Cross by Pietro Lorenzetti and the Annunciation by Fra Angelico. The museum also exposes the precious pontifical vestments belonging to cardinal Silvio Passerini.

As you will see, Piazza Duomo is characterized by a natural terrace, with a beautiful view over the surrounding valleys, so you can take panoramic pictures with your beloved ones!

Unfortunately we had to end our trip around Cortona here, because we hade to take our way home, but if you have some more time, Cortona still has quite a lot to offer. Amongst the most interesting monuments, we suggest the following:

  • Melone I and II of Sodo
  • Eremo Le Celle
  • Grifalco Fortress
  • Church of San Francesco
  • Church of San Niccolò
  • Abbey of Farneta
  • Church of Santa Maria delle Grazie al Calcinaio
  • Basilica of Santa Margherita

We’ve given you quite a lot of “work” to do, now it’s your time for a trip to Tuscany!

Our Tip: The towns included in these areas are quite small and you can easily and quickly visit them. We suggest you to book a place to sleep somewhere in the middle, like Lucignano or Trequanda, so that you can easily and quickly reach all the surroundings.