A Road Trip Through Italy’s Val d’Orcia

In 2011 I spent Christmas in Italy during a break from teaching English in France. After two weeks of train rides between Milan, Venice, Florence, and Rome, I was set on returning one day to see more of the country. And hopefully by car.

I won’t lie and try to tell you that movies like Under the Tuscan Sun and Letters to Juliet didn’t play a role in my wish to zoom around the Italian countryside in a (preferably) tiny and stylish European car. They totally did. The idea of hopping behind the wheel, hitting the road, and stopping whenever and wherever I wanted to sounded so incredible. I figured it was unlikely that I would spontaneously buy a fixer-upper farmhouse – although a girl can dream – but I knew that a plate of pasta would never be too far away, and that felt exciting enough for me.

In March of this year I was finally able to spend some time experiencing Italy this way. More specifically, Tuscany. Even more specifically, the Val d’Orcia. It may have been Dan behind the wheel, and our car was a modern Fiat instead of a vintage Peugeot. But we hopped in and hit the road all the same, and it was worth the wait.

(In the interest of not perpetuating the myth that travel is glamorous all the time, in reality we hopped behind the wheel, hit the road, got lost, stopped at a gas station, received a handful of very sweet road diagrams from a helpful employee, finally decided to turn on our cell phone data, and then zoomed off to make my dreams come true.)

The Val d’Orcia

Italy’s Val d’Orcia is a UNESCO World Heritage Site. Its rolling green landscape dotted with Cypress trees, winding roads and hilltop villages are likely the exact scenery you picture when thinking about rural Italy.

We spent two days driving around the Val d’Orcia to enjoy the local culture, the views, the wine, and the food. Especially the cheese. Oh, the cheese! Here’s a rundown of where we stopped and what we loved. (Hint: basically everything.)

At the end of the post I’ll link to our route map. Bookmark it to use for your next Italian road trip!

Montepulciano

Montepulciano was our home base during our weekend in the countryside. We stayed at Agriturismo Pacifico and loved it. The quiet space has three guest rooms, a cozy common area and an outdoor space with beautiful views.

A varied breakfast buffet was served each morning, our table denoted by a little sign with our guest room’s name.

After settling in at the guesthouse on our first day, we decided to walk into the town center. We weren’t looking for anything specific but assumed we would happen upon the main piazza eventually. Even though Montepulciano is literally referred to as a hilltop town, we didn’t connect the dots that we might have a pretty steep walk ahead of us.

After passing through the Porta al Prato – the main city gate leading to the historic center – and following the signs for Piazza Grande up, up and up, we were a bit more tired than we had originally bargained for. The upside? We had a pretty amazing vantage point for sunset.

We later learned there is a shuttle that regularly runs to the top of the town and back… but where’s the fun in that?!

Montepulciano Highlights

Delicious food and warm service at La Vineria Montepulciano. This pint-sized wine bar creates gorgeous charcuterie boards to share between the members of your party. They’re piled high with local cheeses, cured meats, nuts, fruit and more.

Paired with the local wine (which happens to be world-renowned), it was one of my favorite meals of our whole trip. They even surprised us at the end with a small dessert and encouraged guests to write a message before leaving.

Reservations at this tiny and popular spot are recommended – we stopped by in person on our first night in town and made one for the following evening.

Sunset from the top of town, of course. For the best views, head to the Piazza Grande. Facing the Palazzo Communale, or Town Hall, follow the pathways on either side of the building heading away from the piazza. You can also continue along the Via Ricci past the Piazza Grande for another great vantage point by the Museo Civico Pinacoteca Crociani.

The Temple of San Biagio. This beautiful 16^th-century church sits just outside of town. You may see it in the distance from your sunset viewpoint, but I would recommend driving right up to it as well.

Wine tasting at Talosa Cantina Storica. I’m no oenophile – whenever I’m tasked with choosing a bottle of wine, I still go by the one with the coolest label – but I didn’t want to miss tasting some of the region’s most revered varieties. Montepulciano is known for its Vino Nobile, a red wine with DOCG status made primarily from the Sangiovese grape.

At Talosa, you have the option of enjoying a free tasting or, for a more involved visit, booking a private tour. We chose the free tasting as we squeezed in a visit at the end of our second day. Before sitting down at their small counter to try a few varieties, they sent us to their underground caves to check out some of the gigantic wine barrels found many levels below the tasting room’s floor.

Pienza

The tiny town of Pienza is located a short drive from Montepulciano. We spent about an hour leisurely wandering the increasingly picturesque streets and appreciating the fact that Italians really know a thing or two about curb appeal.

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Along one of edge of town you’ll find a terrace walkway with lovely panoramic views over the cypress-filled countryside.

Piazza Pio II is a beautiful square and home to the town’s duomo, the Palazzo Piccolomini and a handful of other grand buildings.

Pienza Highlights

One word: pecorino.

Pienza is famous for its sheep’s cheese and you will find plenty of places to sample it, see how its made, buy some to take home and more. We stepped into the bustling storefront of Marusco e Maria Enoteca to sample a few varieties and package some up for a picnic.

Side note: One of the phrases Dan and I practiced the most in Italy was, “May I taste?” (Posso assaggiare?) We figured it would come in handy and it definitely did!

Pit stop: La Cappella della Madonna di Vitaleta

This tiny, beautiful chapel is a fun stop between Pienza and San Quirico d’Orcia. You can spot it from the main road (SP 146) but you can also follow signs to take a short detour, park and then walk the rest of the way to see it up close.

San Quirico d’Orcia

Continuing along our Val d’Orcia route, our next stop was in San Quirico d’Orcia. This peaceful and stunning town ended up being my favorite of all of the places we visited.

Just as we did in Pienza (and everywhere else on this list, to be honest), we enjoyed simply walking along the streets and taking in the architecture, street scenes, local businesses and pieces of everyday life.

For whatever reason, there were next to no tourists in San Quirico d’Orcia, allowing us to enjoy our time there even more.

San Quirico d’Orcia Highlights

Taking a coffee break at Bar Centrale (one each day, in fact) while enjoying views of the Chiesa di San Francesco.

Wandering the lush and tucked away corners of the Horti Leonini, a public garden.

Pit stop: Cypress Grove

If you’re as excited about seeing Tuscan cypress trees as I was, you’ll want to pull over to enjoy the Cipressi di San Quirico d’Orcia. Put exactly that into Google Maps and you’ll find a cluster of the towering green beauties along SR 2 (on your left as you’re heading out of San Quirico d’Orcia toward Montalcino).

Montalcino

Montalcino is a wine lover’s paradise. While Montepulciano is known for its Vino Nobile, Montalcino is celebrated for its Brunello wines.

While other wines in the region are made with a majority of Sangiovese grapes combined with other grape varieties, Montalcino’s Brunellos are made from 100% Sangiovese grapes. The town’s impressive hilltop perch and specific climate make the land particularly conducive to cultivating perfectly ripe vines for wine making. (That’s my simplified version, anyway, shaped by my limited understanding of the many intricacies involved in this process!) Many say Montalcino’s wine is the best in all of Italy.

Montalcino Highlights

The expansive views from the terrace by the Madonna del Soccorso church were incredible. We were there in March, so I can only imagine that it becomes even more beautiful as the warmer weather sets in.

Enjoying more quintessentially Italian street scenes.

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Monticchiello

The fastest route between Pienza and Montepulciano is SP 146. This route has beautiful views, but if you can, take the southern route between the two towns as well.

Heading out of Pienza on SP 18 will soon connect you to SP 88. SP 88 will lead you right into Monticchiello.

You’ll get amazing views of Pienza and there are a lot of scenic pull-offs and classic cypress-lined drives. (Including the one from Gladiator, which didn’t mean much to me at the time, but I’ve since watched it!)

You’ll find that Monticchiello is very tiny, but unsurprisingly beautiful and definitely worth a walk around.

Plus, the countryside views from its hilltop perch are amazing. (That’s right – more hilltop countryside views. Better keep those camera batteries charged!)

Monticchiello Highlights

Stumbling upon a small public garden full of interesting artwork.

Pit stop: La Foce and Dopolavoro La Foce

La Foce is a countryside estate boasting multiple villas and impressive gardens. The gardens are open for guided visits on Wednesdays and weekends for part of the year. (This year, they opened on March 30th and will stay open through November 3rd.) Learn more here.

Right down the road from La Foce is Dopolavoro La Foce, a well-reviewed restaurant that originally opened in 1939 to cater to the nearby estate’s workers. Even if you aren’t hungry, pull over in the parking area across from the restaurant to enjoy one of the Val d’Orcia’s most popular views: an especially windy road lined with Cypress trees called the Strada di Valdoresi.

Bagno Vignoni

Bagno Vignoni is another tiny but worthwhile town. Its main square is actually a medieval thermal bath.

You can’t bathe in its waters, but there are places nearby where swimming is allowed. (More on that soon.) We found a little section that was perfect for dipping our feet in, and the couple next to us was reading the paper together while doing just that. It was precious.

Bagno Vignoni Highlights

Fueling up for the rest of our day at La Bottega di Cacio. This small grocery store with a deli counter is the perfect place to assemble a picnic. Dig in at one of their outdoor tables or save it for another point along your route.

With our limited Italian, it was especially helpful to be able to build our plates by simply pointing at whatever caught our eye in the glass case. Marinated stuffed peppers, crunchy garlic sprouts, and of course, a few wedges of pecorino.

Bagni San Filippo

From Bagno Vignoni we continued on to Bagni San Filippo. This area is a slight detour from our main Val d’Orcia route, but we were excited to check out its natural hot springs.

Once we found the path leading to the best parts for bathing, it was bizarre but fun scrambling around to try all of the different pools. Some parts were super hot and people were parking there for way longer than I could handle!

This huge calcium formation is known as the balena bianca, or white whale.

Bagni San Filippo Highlights

Enjoying the unique scenery while spending an afternoon doing something entirely different from anything I could do at home.

Pit stop: Cugusi Silvana

This stunningly situated pecorino maker will gladly let you sample some of their award-winning cheeses. They’ll even vacuum seal any purchases so that you can safely take them all the way home with you. Looking for a full meal? They’ll arrange a picnic basket for you based on the number of people in your party. You can then take the basket and enjoy it anywhere on their beautiful grounds overlooking lush green fields and Montepulciano in the distance.

Side note: We stopped here on our second day after making our way back to Montepulciano from Bagni San Filippo by way of San Quirico d’Orcia. It’s located just outside of Montepulciano on the way to Pienza, so you can plan a stop here whenever it makes the most sense for you.

Our Val d’Orcia Route Map

Here’s a map of our driving route through the Val d’Orcia that you can save for later!

A few notes: This map shows both the northern and southern routes between Montepulciano and Pienza, as referenced in the Monticchiello section. The destinations aren’t necessarily listed in the order we visited them, but it does show all of the exact roads we traveled. For the most part, we visited the top half of the route on our first day and the bottom half on our second day. Also, none of the pit stops are listed specifically on the map, but they are all found somewhere along these routes.

Due to the proximity of the different towns and stop-offs, we were able to enjoy a laidback pace throughout our Val d’Orcia weekend. We rarely felt rushed. As we were there during shoulder season, the roads and towns were generally uncrowded. This made it easier to navigate and find parking. Despite visiting a handful of towns, we knew we were barely scratching the surface of everything rural Tuscany has to offer. I would highly recommend a road trip in this area!

Have you been to Tuscany or the Val d’Orcia before? What did you think?

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