There are few places better suited to a road trip than the beautiful sun-kissed Val d’Orcia. 

On trips to the area I’ve stopped in Siena, Monteriggioni, Buonconvento, Montalcino and Montepulciano. Each are a quintessential Tuscan town: small, gorgeous, filled with wine and perched on a hilltop. Siena being the only truly influential town in the area’s history. 

Dodging the potholes and cyclists as much as possible while still ogling our surroundings, there was one other town in Val d’Orcia that we absolutely had to see: Pienza.   

Pienza, Tuscany

Pienza is more village than city. Located between Montalcino and Montepulciano, a stop makes sense if you’re looping the area by car. Pienza as we see it today was essentially created by Pope Pius II, who was determined to transform his hometown into his idea of the perfect Renaissance city. He poured money and influence into it, creating a beautiful central piazza known as Piazza Pio II and the buildings that surround it: the Piccolomini Palace, the Borgia Palace and the cathedral.

Located in UNESCO World Heritage Site Val d’Orcia, Pienza itself has enjoyed UNESCO World Heritage status since 1996 thanks to Pope Pio II. 

Pienza, Tuscany Pienza, Tuscany

Beyond the main square, the sandy bricks of the buildings frame gorgeous doors and ancient houses, restaurants filled to the brim with cinta senese ragù and the infamous local pecorino cheese and overly-romantic street names. Tourists stroll down Via del Bacio (Kiss Street) and Via dell’Amore (Love Street), snapping pictures of the suggestive names. 

Pienza, Tuscany

Besides the exaggerated street names, there is little as romantic or breathtaking as the panorama stretching out beyond the city walls. A natural balcony, the view from Pienza stretches across the greater part of the Orcia Valley, offering low-hanging clouds and undulating fields that range from vibrant summer green to burnt amber depending on the season.  

Pienza, Tuscany

Pienza is small – you don’t need to dedicate much time to get a feel for this village – but it’s well worth exploring. Known as the capital of pecorino cheese because of its sheep that live the life in the beautiful valley, the town has the best local dishes Tuscany has to offer. Think truffles, prime cuts of beef, homemade cheeses and fresh pasta. You’ll find Tuscany’s famous leather goods, artisan ceramics and artwork and small boutiques, but no souvenir is as relevant or delicious as a hunk of truffle cheese… or maybe that’s just me. 

Pienza, Tuscany

The charm of Tuscany is found in its small towns, its known and lesser-known villages. For me, the charm is in the beautifully-kept balconies, the local dialect and the hyper-local food. A roadtrip in Val d’Orcia, Tuscany is a perfect way to explore these tiny hilltop towns, to slow down and soak in the atmosphere and history, and Pienza is a beautiful stop along the way! 








Written by ginamussio

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