Tuscany Road Trip: Siena and Val d'Orcia

Discover the real Tuscany road trip you've seen in the movies right from your own car.

Siena, San Gimignano, and the Val d'Orcia will not disappoint.

When you type “Tuscany” into Google Images, you find green rolling hills with gentle curves. Like turtle shells, stacked one after another until the horizon fades out of sight, dotted with tall, dark cypresses pointing to a blue sky scattered with fluffy, passing clouds. Sometimes, these cypresses line a zigzagging path; other times, the meadow is blanketed in poppies, or has turned a warm yellow-orange after the summer heat. In the background, or just behind the ridge, you can spot a rustic farmhouse.

These are images that radiate peace and pure inner calm. And from that moment on, you might just start dreaming of traveling to Tuscany. That’s exactly what happened to me.

But watch out, Tuscany is huge and packed with charming medieval towns and gorgeous scenery, though not all of them look exactly like the ones in those photos—it all depends on where you go.

If you fell in love with those pictures just like I did and want to see these landscapes with your own eyes, you'll need to head to the Val d’Orcia, in the province of Siena.

Feel free to grab some inspiration from this 3-day road trip we took back in April 2015.

Siena

Siena has always been considered Florence's rival, and I must say, in my opinion, it’s a really close call. If you want to know more about Florence, don’t miss the post Strolling Through Florence.

Siena's city center is a beautifully preserved medieval town—and for good reason, it's a UNESCO World Heritage site.

Small and easy to explore on foot, it sits perched atop a hill. You can easily wander through it in a single day and check out its top highlights, like these:

Piazza del Campo

It’s a unique, slanted fan-shaped square right in the heart of Siena.

Twice a year (specifically on July 2nd and August 16th), it hosts the Palio di Siena, a famous horse race where Siena's rival districts compete against each other.

At the lower end of the square sits the ‘Palazzo Pubblico’, which houses a museum and the ‘Torre del Mangia’, offering spectacular views of the city and surrounding hills. Tower admission was €10/adult in 2015.

Duomo

It’s part of the Opera Metropolitana di Siena complex. Built in Gothic style, it boasts a gorgeous white, green, and red marble facade.

Its interior is even richer than the Duomo in Florence, and tucked off to one side is the Piccolomini Library, which is said to be an absolute must-see.

We couldn't go inside because Holy Thursday Mass was underway, but we’ll definitely be back.

The Opera Metropolitana di Siena also houses the Opera Museum, a baptistery, and the crypt.

Where to sleep

We spent a night at B&B Le Chiarine.

It offers great value for money, with spacious and clean rooms, plus comfy beds. Breakfast is simple yet hearty.

It’s located in a quiet residential area, slightly outside the medieval center, with an easy 10-15 minute walk into town.

A huge bonus of this stay is the view of the Duomo towering over the city, which you can catch near the B&B on your way to the center. We wouldn't have enjoyed it if we hadn't spent the night there, and trust me, it’s totally worth it.

Plus, around B&B Le Chiarine, it's easy to find free parking (a pretty rare find in Italy!).

Just make sure to check the street signs at the start of each block to see which day street cleaning takes place, as cars must clear out from one side of the street to let the street sweepers pass at the scheduled time.

Val d’Orcia

Below, I’ll take you through the route we followed in the Val d’Orcia—a photo-worthy road trip through some of Tuscany's most pastoral landscapes.

Remember, especially on this route, it's all about enjoying the journey.

San Quirico d’Orcia

This was our first stop after leaving Siena. A charming, walled medieval village perched on a hilltop.

Cobblestone streets with flowers in the windows, the quaint little church of ‘Collegiata dei Santi Quirico e Giuditta’, and the ‘Horti Leonini’ gardens will make your visit a truly pleasant stroll.

La Foce

If you check out the route map at the bottom of the page, you can see the drive we took from San Quirico d’Orcia to La Foce. I highly recommend taking the exact same path!

Here you'll find all the photos you want to take on this trip.

You'll be able to pull over at viewpoints or wide shoulders along the road and spend minutes—or hours—etching into your memory winding cypress-lined roads that lead up to a farmhouse on a green hill.

Wherever you look, you'll be amazed.

La Foce isn't a town in itself; it's an old estate with gorgeous gardens and several types of rental accommodations in a privileged setting—all of them quite pricey.

We didn't go inside, but I recommend walking around its outer wall down to the lowest part. From there, you can admire one of the most photographed cypress zigzags, which you'll have already spotted from the road. But this time, you'll see it straight on, without any telephone lines or trees getting in the way of the view.

Simply breathtaking.

Monticchiello

Monticchiello is a delightful medieval village, once again perched high on a hill.

Enjoy the views of Tuscany, with Pienza in the background, stroll along its cobblestone streets and, if you can, have lunch, dinner, or grab coffee and pastries on the terrace of restaurant ‘La Porta’.

The location alone would be reason enough to recommend it, but on top of that, the food and wine are amazing. Make sure to call ahead and book, though, or you won't get a table.

Pienza

This is another walled medieval town, slightly larger than Monticchiello, perched on a hilltop with winding alleys and gorgeous views of the Tuscan valley.

We stayed here at ‘Piccolo Hotel La Valle’, a very clean and decent 3-star hotel offering free parking and a simple breakfast included in the price. Being just outside the city walls, it was super quiet at night.

Montepulciano

Montepulciano is a walled medieval town with quite a few slopes and steep hills perched on a ridge, the most touristy of all the ones we visited in the Val d’Orcia.

It's famous for its wines, so it's no wonder it's dotted with wineries offering tastings to visitors.

Architecturally speaking, in my opinion, its biggest standout feature compared to other medieval towns in the area is the colossal San Biagio Sanctuary (Santuario della Madonna di San Biagio): a temple located at the foot of the hill where Montepulciano rests.

As you approach it from Pienza, you'll get to admire this wonderful picture-perfect scene, which photography lovers will absolutely adore.

San Gimignano

Our last stop was San Gimignano, north of Siena, in the Val d’Elsa.

This small walled city is dotted with towers (although there used to be many more, only 15 remain standing), making it look like a medieval New York. Wealthy families showed off their power by building towers taller than everyone else's, hence the town's unique skyline.

San Gimignano is internationally famous, or in other words, very touristy. You'll understand why once you see it with your own eyes, though it means sharing its streets and squares with hundreds of people, which takes away quite a bit of its charm.

We were very lucky, as it poured rain the day we visited.

Sure, we were dashing around with a battered umbrella trying not to get soaked, and the sky was gray, which didn't do the photos any favors.

But the streets were almost deserted—everyone had taken shelter in bars, restaurants, hotels…

Suddenly, that town felt genuinely medieval: gray stone, soaked by relentless pouring rain, empty… It felt like we had traveled back in time.

We spent the night at ‘Agriturismo Sulle Orme Di Dante’, with free parking just a short walk from town.

I recommend walking—the parking lot outside the walls is pretty expensive and fills up quickly (as long as it's not pouring, like it was for us).

This agriturismo has lovely decor with vintage furniture in both the rooms and bathrooms, all very well kept and clean. Plus, it has a pool in the garden overlooking San Gimignano.

Breakfast is good, but it's not included in the rate—you have to pay for it separately.

In San Gimignano, I can recommend ‘Pizzeria Ristorante Il Trovatore’, outside the town walls. Delicious pizzas and Florentine steak. Remember to book well in advance by phone if you want a table here.

If you have any questions or doubts, or need extra details I haven't covered, don't hesitate to leave a comment below. I'll be more than happy to help you out!

Useful links

• B&B Le Chiarine.
• Other hotels in and around Siena.
• La Porta, Monticchiello.
• Piccolo Hotel La Valle, Pienza.
• Agriturismo Sulle Orme Di Dante, San Gimignano.
• Flights to Italy: Trabber, eDreams, Momondo, and Vueling.
• 5% discount on IATI insurance.

Oh! And if you're touring Italy, don't miss these blog posts:

• Venice in low season.
• Weekend in Rome.
• A walk through Florence.
• San Galgano Abbey in Tuscany.
• Lake Como itinerary.
• Maremma Natural Park and its pristine beaches.
• Bologna, the city of porticoes.
• Road trip through Umbria, Tuscany's secret neighbor.
• The wonders of the Amalfi Coast.

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