Driving around in Tuscany is one of the best ways to appreciate its scenic countryside. With this Val d’Orcia itinerary we take you around one of its most enchanting areas, to discover why it’s considered the jewel in Tuscany’s crown.

The Val d’Orcia is an area south of Siena that has a unique beauty all of its own. With its verdant rolling hills, poetic views and picturesque villages, it’s an unspoiled paradise for visitors, and a UNESCO site of outstanding beauty.

tuscan countryside

Enjoy the best of the Val d’Orcia in a day

Take the SR2 from Siena and head south, towards a world of pure beauty and enchanting views. These are the vistas that have made Tuscany famous. The graceful rolling hills punctuated here and there with cypress trees. The solitary country churches set in the midst of fields. All of it creating an atmosphere of idyllic tranquility.

Revel in the old-world-charm of small towns like Pienza and San Quirico d’Orcia, where stone is the colour of honey, flowers pots dot the streets and even the simple old doors have you reaching for your camera. Find old-fashioned botteghe, quiet sun drenched squares and trattorie where the traditional pici pasta is served with the local pecorino cheese.

Are you ready for the Valdorcia? The trick is not to rush. The pace is slower here, so you’ll be able to take your time, drive slowly and enjoy the new sights behind every bend in the road.

val d'orcia

Val d’Orcia itinerary – Buonconvento to Montalcino

Starting from Siena take the SR2 direction south. Stop at the tiny walled village of Buonconvento, whose name tells you everything. It means “happy, lucky place”. After a cappuccino break, drive on to Torrenieri where you take the SP14 to Montalcino. Its huge Medieval fortress dominates the valley, and welcomes the visitors to Val d’Orcia’s wine capital. Wine lovers know the place well, and come here to sample the local speciality – the famous wine Brunello di Montalcino.

Montalcino offers plenty of wine tasting opportunities, shopping for local delicacies and if you’re in the mood for a bit of Medieval art, you can poke your head inside the Museo Dioceziano. After lunch it’s time to go back onto the SP14 road, towards San Quirico d’Orcia, to one of the most scenic stretches of road in the whole of Tuscany.

⇒ Top tips on How to Plan a Road Trip to Tuscany.

DETOUR: If you’ve got time you can visit Monte Oliveto Maggiore, an active monastery set in an impressive location that boasts some intriguing Renaissance frescoes. (it is 9 km. from Buonconvento, in the area of the Crete Senesi).

scenic drives in tuscany

Pure beauty – from San Quirico d’Orcia to Pienza

We have a soft spot for the small, quiet town of San Quirico d’Orcia. The main sight is the Collegiata, an evocative Romanesque Church built at the time when pilgrims were passing trough here on the Via Francigena. The weathered lions guarding the entrance, and the monsters sculpted on the portals are simply fascinating.

After a relaxing stroll around the Horti Leonini Gardens, back to the road to reach Pienza. Along this scenic stretch of the SP146 road you’ll spot the famous Vitaleta Chapel seen so many times on the classic postcards of Tuscany. Taking a picture of this chapel is a must on any Val d’Orcia itinerary.

=> Discover some truly magical places to visit in Tuscany.

=> 5 Picturesque small towns to see in the Val d’Orcia!

Pienza is the queen of the Val d’Orcia, a delightful small town with a history as impressive as its views. It is a town literally born from a dream. Silvio Piccolomini, aka Pope Pius II, employed the architect Rossellino to convert his home town into a place where the ideal of the Renaissance could be translated into an architectural plan. Have a look for yourself and decide if he succeeded. Visit the Palazzo Piccolomini and enjoy a walk around the town with stunning views over the valley. If you have dinner in Pienza, the trattoria Buca delle Fate is the one to try. Pecorino served with honey, and the local salumi are a must.

DETOUR: Bagno Vignoni – The town is built around a great pool of thermal water. Unfortunately you can’t have a refreshing swim here, but the effect is truly wonderful, with the stone houses reflected in the water (6 km. from San Quirico d’Orcia).

Find out about the most romantic destinations in Tuscany. And 10 charming small towns to visit.


The best time of the day to take pictures is early morning and late afternoon, an hour or so before sunset. This is when the colours of the countryside and details in the towns are at their most photogenic.

VAL D’ORCIA ITINERARY TOTAL DISTANCE: 70 kms – Using Siena as a starting point this route will take one day.

For more road trips ideas, check out our article about the most scenic drives in Tuscany.

val d'orcia itinerary