Pienza and the Val d’Orcia – Perfect Symmetry to Amazing Scenery

Pienza and its city walls

There is good reason that central Tuscany is on most travel bucket lists – it’s almost a perfect combination of history, culture, food and scenery. Pienza, noted to be the “ideal” renaissance city, is not as well visited as Florence or Siena but I think is worth a trip especially to spend time roaming and driving through the surrounding Val d’Orcia which contain so many iconic Tuscan scenes.

Pienza's main cathedral
Pienza’s cathedral’s facade
Mailboxes in Pienza
Perfect mailboxes
Entering Pienza
One of the main entries to the city

I was here last year in May and unfortunately my trip coincided with a long weekend in Italy so Pienza was exceptionally crowded with local visitors. Part of this is because Pienza is fairly easy to get to being just over a two hour fifteen minute drive from Rome Airport and around one and a half hours from Florence. I stayed the week nearby in La Bandita (see blog), which gave me time to max my exploration of this area without having to drive too much.

Pienza and its city walls
View of Pienza from the road leading to it

Pienza is called the ideal Renaissance city because this is the first city where town planning was taken seriously when Pope Pius II hired an architect to renovate his hometown. So it was here that the town square became a key focal point with main buildings such as the town hall and cathedral surrounding it. It’s not a big place so around two hours should be adequate (excluding the time spent looking for parking). If you plan on eating here, allocate more time. Some of the best pecorino cheese comes from the area. We also found some nice linen stores so shopping may also take a bit of time.

Pienza's main cathedral
Pienza’s main cathedral sits next to the town hall on the main square
Pienza's town hall
Looking up at the town hall’s facade
Shopping in Pienza
All sorts of stuff to look at

From Pienza, if you have time you can do a walk around the city on the hill that it sits on or in the surrounding countryside. A roundtrip probably takes around three to four hours. I didn’t have time for this so I opted to drive in search of one of the more iconic scenes in Tuscany – that of a tiny chapel. It’s called the Chapel of Our Lady of Vitaleta and it sits between some farm land. We found it after taking numerous wrong turns and had to park the car on a dirt road to walk through a gate to get to the chapel. I’m not completely sure I’ll find it again. But if you have time and the interest, I think it’s worth it – the setting is very pretty, especially on a sunny day. If I had more time, I’d take the walk here from Pienza and back.

Iconic tuscan chapel with cypress trees
Approaching the Chapel of Our Lady of Vitaleta  – this is actually the back of it
Chapel of Our Lady of Vitaleta
The front of the chapel

The valley south of Pienza is known as the Val d’Orcia or the Orcia Valley. The Orcia is a river that runs through the area. This is an agriculturally rich part of Tuscany with the hills planted with grapes for wine and wheat for pasta. Since I was here in early May, the valley was green but in the summer, the wheat fields will be golden (see photo below). I’m sure it must be stunning when the lavender is in bloom as well. But besides the tall cypresses, the hills are also dotted with the remnants of medieval towers.

Medieval tower in central Tuscany
A medieval tower stands in the Val d’Orcia
Winding roads, hills and cypresses in the Val d'Orcia
A famous scene of a winding road in the Val d’Orcia
Val d'Orcia sheep
I took this photo during a prior trip in July – when the hills turn golden

Some of these scenes are well known as they’ve been featured in movies such as The Gladiator and The English Patient. The winding road above is a frequently pictured scene with the cypresses lining the way up the hill. Notably, it was also the road the we drove up and down every day while we stayed at La Bandita. There were great views from the road itself too.

Another iconic tuscan scene
Another view of a winding road in the Val d’Orcia

If you have time, you may want to spend a couple of hours exploring Montepulciano, which is just a 20 minute drive from Pienza. Unfortunately my visit got rained on which meant we sat in a wine bar drinking at eating salami. Not a bad thing (but no photos, alas).

A good place for dinner nearby is Osteria La Porta (website: http://www.osterialaporta.it/en/) which is just inside the wall of another small town, Monticchiello (20 minutes drive from either Montepulciano or Pienza). This is a simple restaurant but with very good pasta and meat. Since we were there in early May, spring lamb was on the menu and this was very good. The owner is jovial and welcoming and this made our visit all the more enjoyable.

Montichiello's entrance
Behind the wall to this town is a great eatery – Osteria La Porta