A Val d’Orcia Scenic Drive to Discover the Wine Region of Tuscany: What to Do, Where to Stay, and What to Eat. A Four-Day Road Trip Itinerary from My Travel Journal

HOW TO GET TO AND WHERE TO STAY IN VAL D’ORCIA, TUSCANY

Here we are: under the Tuscan, wintery, beautiful sun. With our Gambero Rosso Food & Drink Guide and facing an amazing valley called the Val d’Orcia region of Tuscany.

This is the Italian version of paradise.

We got here yesterday: getting to Val d’Orcia from Rome takes a two hours and forty minutes car drive, more or less.

Our base is in Montalcino, in a cute tiny hotel, surrounded by pines & cypresses and some of the best winemakers of the peninsula.

DAY 1: MONTALCINO

MONTALCINO: WINE, FOOD, AND TUSCAN CHARM

Yesterday, upon our arrival in the Val d’Orcia valley, we had an aperitivo in Montalcino: a glass of the world-famous Brunello di Montalcino, bruschetta, and crostino toscano (chicken liver pâté – sounds awful, tastes delicious).

Two hours of tasting and chatting, no one pressing us out to give the table to someone else, no one asking us to order more food to stay: surreal for us people from Rome.

After a fifteen-minute walk through the beautiful, Christmas-decorated streets of Montalcino, we were already seated for dinner.

A glass of wine, bruschetta, and our Tuscan antipasto: salami, prosciutto, mushroom, onion, and more crostino toscano.

Polenta for me, and wild boar for Luca.

Back to the hotel, time to watch some TV – less than 15 minutes of a cooking show, and we were asleep, dreaming of vineyards, good wine, and excellent Tuscan food…

TUSCAN FOOD FACT N. 1

Tuscan bread has no salt.
There is a historical explanation: the past high prices of salt. But I prefer the gastronomic answer: all the other flavors of Tuscan cuisine are so intense you must accompany them with a plain, simple flavor.

DAY 2 OF THE VAL D’ORCIA SCENIC DRIVE: SIENA & MONTICCHIELLO

Siena

After a very nutritious breakfast (poor things, we’re eating so little these days…), we decided to drive to the beautiful, magical city of Siena in Tuscany.

We were welcomed by the impressive Piazza del Campo, the one where the Palio is raced – one of the most extraordinary places I’ve seen in my life.

Still more impressive when we climbed up Siena’s Torre del Mangia (400 steps are a lot, but we were motivated: we were burning the upcoming lunch calories – yeah, sure).

Anyway… after the climb, we visited the “Antica Pizziccheria Miccoli,” a historic grocery store in Siena. Unfortunately, photos were forbidden, so I cannot show you the mustached showman behind the counter. While wrapping up boar salami, pecorino cheese, and Tuscan crostini seasoning, he was talking, smiling, laughing, and slicing prosciutto, cheese, and salami for us, so we had an aperitivo right there while he was packing our stuff.

After the climb, we visited Antica Pizziccheria Miccoli, a historic grocery store in Siena. Unfortunately, no photos allowed, so I cannot show you the mustached showman behind the counter. While wrapping up boar salami, pecorino cheese, and crostini seasoning, he was slicing prosciutto, cheese, and salami for us – we had an aperitivo right there.

Tuscan people are so elegant! I’m impressed. They have understatement and that calm only people used to beauty and charm have. Decorations are tasteful, details are impressive, streets are spotless, and people are so educated…

Lately, being Italian didn’t feel like something to be proud of. But these days, I realize that’s just Rome. There’s more to Italy than chaos and politics.

I left the shop with my mouth and hands full of cheese and local bread, ready for…

LUNCH, of course.

At the Compagnia dei Vinattieri, we savored Tuscan red wine while waiting for our adventurous antipasto: tongue.

It wasn’t easy to get the first bite; it never is…

But we had to: we are foodtrotters!

It was so hard not to think that a tongue was on my tongue…

But the truth is: it’s just meat. Tastes like meat. Looks like meat. I just don’t feel the urge to repeat the experience.

What came next was much better: pumpkin soup with balsamic vinegar and caramelized leeks, and pappardelle al ragù.

Finally, the traditional sweet ending: Cantucci & Vin Santo – almond cookies dipped in sweet wine (in case you haven’t drunk enough).

TUSCAN FOOD FACT N.2

The most famous traditional pasta shapes in Tuscany are Pici (or Pinci) and Pappardelle.
But there are also tons of delicious, hot, tasty Tuscan soups.

MONTICCHIELLO: A HIDDEN GEM IN VAL D’ORCIA

In the afternoon, a wonderful surprise: we drove from Siena to Monticchiello, the tiniest, cutest village I’ve ever seen.

Monticchiello reminds me of Calcata: perched, decorated, tidy, with a stunning view… only 80 people living there!

At the tourist info point, we met Mr. Roberto, the most clever cicerone ever. He took us around the village and even introduced us to a Teatro Povero rehearsal – something this tiny place is world-famous for.

You know how theater makes people hungry, right?

So imagine how much we enjoyed our Tuscan dinner back in Montalcino (Re di Macchia restaurant): a 1-kilo Fiorentina steak, boar Pici, and honey “cacio e pepe” croutons…

This time digestion was tough; I could hardly sleep, despite the wine. Detox plans for next week…

DAY 3 OF THE VAL D’ORCIA SCENIC DRIVE: MONTEPULCIANO & PIENZA

Montepulciano

Nope, we didn’t comply with the “let’s eat light” resolution… but I am still counting on the detox plan.

After our usual “nutritious” breakfast, we drove to Montepulciano, a Tuscany wine town totally dedicated to… guess… wine!

Also famous among Twilight Saga fans as a Volterra filming location.

We climbed up the fortress and explored a surprisingly authentic Montepulciano, with artisanal shops, wineries, and fewer tourists than expected.

We found a cute Christmas market in Piazza Grande and bought a unique cinnamon beer jam (for cheeses), then devoured a burger: Chianina meat, truffle cream, and mushrooms.

To cheer up after missing out on other stands, we had a cup of vin brulè (mulled wine) and a delightful chat with the guys at the polenta stand – one of them even shared his perfect polenta recipe.

Later, we visited Cantina De Ricci, an ancient wine cellar where some Twilight scenes were filmed. We walked through caves and oak barrels, ending with a wine tasting and buying six bottles of Montepulciano.

TUSCAN WINE FACT N.3

Some of the best Tuscan wines, known as Super Tuscans, have no DOC or DOCG.
Winemakers are free to experiment—manna from heaven for wine lovers.

PIENZA: CHEESE HUNT AND HOLIDAY TOURISM

Here comes the bad of this Val d’Orcia scenic drive…

In the afternoon, we drove from Montepulciano to Pienza, to see the little village and to buy the famous Pecorino di Pienza.

I was excited: I had read there were different flavors and wanted to bring some back home.

Well… I entered three different cheese shops in Pienza and bought… nothing.

I entered the first one, captivated by the banner announcing at least twelve different flavors. But when I asked for them, they didn’t really have them.

I entered the second shop, fascinated by the beautiful shelves full of pecorino cheese.

I patiently waited for my turn while a big family was tasting every flavor in the shop. While looking around, I spotted a basil and pine nut pecorino. So, when it was my turn, first thing, I asked to taste it.

The I-hate-the-world saleswoman rudely answered I couldn’t taste that one. And no, not even the second one I asked for. As I never pay for mistreating, I left the shop.

I entered the third store, a little desperate, nervous, but still wanting my Pecorino di Pienza. When I asked if they could vacuum-pack my stuff (no, I didn’t even want to taste them at that point), again, I was rudely told I would have to wait until they had served everybody in the shop.

So I ended up running away from these horrible people.

As I was a little depressed, my husband took care of dinner reservations…

Here comes the best part of the vacation.

I’ll tell you just one thing, to help you understand how amazing this place (Il Leccio) is: we left the restaurant booking a table for tomorrow night.

I never, never, never do that on the same trip: I’m always looking forward to eating in as many different places as possible. But this time, we had to come back!

DAY 4: VAL D’ORCIA SPRINGS, BAGNO VIGNONI, A VINEYARD AND NEW FRIENDS

Bagno Vignoni pools

Today was the best day of this Val d’Orcia itinerary.
Sadly, the last one.

My breakfast was light (I swear), because I was going to wear my swimsuit (lucky me, I brought the black one).

Why? Hot springs!

We went to Bagno Vignoni, where thermal spring waters face the beauty of the Val d’Orcia valley.

One word: RELAX.

A few more words? A perfect lunch.

Polenta and boar, pici with sauce – I had taken off the swimsuit by then, and who cared for bellies, fat, or calories… I’ll think of them next week.

The sun was high, the temperature perfect, and the food, as usual, absolutely delicious.

At that point, I had taken the swimsuit off, and who cared for bellies and fat and calories… I’ll think of them next week.

The sun was high, the temperature was perfect, and the food, as usual, was delicious.

After lunch, we drove to our wine tasting experience.

The lovely, cheerful Alessandra from the Leccio restaurant had given us the name of a friend of hers: Marcello, a really passionate Val D’Orcia winemaker.

We were looking for the real thing, no touristic paths.

Wine tasting in a vineyard

After lunch, we drove to our wine tasting experience.

The lovely, cheerful Alessandra from Il Leccio restaurant had given us the name of a friend of hers: Marcello, a truly passionate Val d’Orcia winemaker.

We were looking for the real thing – no tourist paths.

So we called Marcello, and he welcomed us to the Collemattoni estate.

We talked for hours about:
Tuscany, boars, and roes.
What a perfect night out for locals looks like: a bath in wild hot springs (those secret places only locals know), followed, of course, by a big Tuscan dinner.

We talked about Food Inc., sustainability, and organic farming.
About being demitarians.
About Nature and humankind.
About wine, food, and gaining weight (of course).

{Italians always talk about food. At work, at home, even while dining out. I’ve noticed that we’re eating at a restaurant and talking about the next restaurant we must try.}

This was our most authentic Val d’Orcia afternoon: tasting wine and honey (also made by Marcello), and promising to meet again (next year?).

Locals – Or friends?

Later that night, we had our delicious dinner again at Il Leccio.

At the end of the meal, drunk on wine and grappa and hardly upright, Alessandra took us to the winery next door.

For two hours, we drank beer, we chatted with Marcello, Alessandra, Gianfranco (owner of Il Leccio), and Fabian(winemaker at La Magia), we drank more beer, we laughed, and we drank more Val d’Orcia-brewed beer.

It was one of those nights with new friends that feel like old friends.

Talking about everything: what’s wrong in this world, what’s right in this world, the places we’ve been, the places we want to go…

And food, of course.

This is the real magic of Val D’Orcia,
this is the secret of life,
this is what I like:
slow food, slow living, and mindful moments when you realize that paradise is probably here, exactly where we are…

If you’re looking for the same nirvana, I heartily suggest you plan your Val d’Orcia trip ASAP!

Enjoy food, life, Italy, and people!
Claudia