Tuscany in Autumn: From Hilltowns to Harvest

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Last Updated on February 19, 2018 by Audrey Scott

As autumn advances, the sunflowers fall, the golden soil is turned for the winter. Grapes, too, are ready for harvest. People celebrate.

Tuscany's poetry is packed in the fields, the hills, the history, the food, and the people who make it all possible.

Earlier this month, we returned to Italy's Tuscany region ten years after we were married there in September 2000. Time can do funny things to one’s perceptions: we wondered if our memories had been unfairly overcome with nostalgia.

Tuscany Travel, Castles and Agritourismos
Our journey through Tuscany, complete with stops at small castles.

When we were married in Tuscany, it couldn't have been that beautiful, could it?

So we returned to investigate. And this is what we found.

Tuscan Landscape

Although the Val d’Orcia is itself a UNESCO site and many of the towns throughout are quite touristy, the region's focus on agriculture remains authentic. Tuscan farmers — the easily forgotten foundation of Tuscany's culinary depth — wave when you pull to the side of the road to admire their craft and to capture another image of the profoundly beautiful soil. Not to be outdone by the Tuscan earth, the sky dazzles, too — particularly as late afternoon autumn light fights to break through rolling thunderstorms.

Tuscany Travel, Val d'Orcia
Late Afternoon Light in the Val d'Orcia

Tuscan Hill Towns

If you look up every few kilometers while driving across Tuscany, you find yet another medieval hill town revealing itself perched cliffside or atop a patch of soft volcanic rock. Pinch yourself, this is no fairy tale. It's all very real, and has been so for hundreds of years.

Tuscany Travel, Pienza in the Distance
View of Pienza in Tuscany

Should you choose to take the climb to your hill town of choice, steep, winding cobbled streets will challenge your heart and reward you by depositing you somewhere within reach of a main plaza, cathedral and town hall.
Tuscany Travel, Montepulciano
Walking Up to the Palazzo Comunale – Montepulciano, Italy

Small towns may even feel abandoned, what with all the shutters drawn. But as lunchtime approaches, the symphony of dishes and pots and pans begins, and the aroma of garlic, tomatoes, and aged cheese wafts from kitchens and fills the narrow streets of old towns. Families gather to eat in the opening act of their afternoon pause.

We do want to mention our soft spot for Pienza. This was the scene of the crime: our wedding, ten years ago, in this UNESCO World Heritage Tuscan hilltown.

When we arrived, we picked up our uphill pace and turned the corner to enter Pienza's main piazza, the scene was that of the Tuscan hill town we remembered. Heads up, Renaissance stone, echoes of Pope Pius II's vision of a perfect town, delis stacked with wheels of pecorino (the local sheep cheese), hunks of wild boar salami, and piles of dried porcini mushroom slices.

But we felt like we owned a little piece of the place. Ten years ago, we ran across the plaza under a shared umbrella while locals chanted “Sposa bagnata! Sposa fortunata!” (a wet bride is a lucky bride). The entire event — from start to finish with all of its twists and turns, shared with friends and family — was wickedly magical and perfect in its own imperfect way.

Tuscan hill towns have this effect on you, whether you get married there or not.

Tuscany Weekly Markets

If you'd like a chance to rub shoulders (literally) with locals and join in animated discussions regarding the differences between Tuscan and Parma prosciutto, stop by one of the dozens of weekly markets. These Tuscan fresh markets are not fancy affairs. In fact, they usually consist of a lineup of delis-on-wheels pulled into a parking lot on the edge of town. Looks can be deceiving. These trucks are chock full of fresh Italian product to fashion your wildest of your gourmet Tuscan picnic dreams.

Tuscany Travel, Pecorino Cheese at the Market
Pecorino Cheese in Tuscany

And the vendors? Friendly and passionate. They focus, they laugh, gesticulating ferociously about who knows what. They enjoy the company of their customers, most of whom they've probably known for years. Tuscan vendors — their pride in product, palpable; their love of food, infectious. Free samples flow, just to ensure you choose the right cheese or smoked meat.
Tuscany Travel, Montepulciano Weekly Market
Preparing the Proscuitto – Weekly Market in Montepulciano


In the course of a week we traveled over 1,300 km (800 miles) through Montepulciano, Pienza, Montefellonico, Torrita di Siena, Montalcino, Cortona, Cinigiano, Manciano, Pitigliano, and Sorano. Even in this context, we barely covered a fraction of Tuscany. The region is vast and deep in geography, life and leisure.

This distance may not sound like much. However, the roads are windy and driving times are often double or triple initial expectations. In other words, if it's “an hour away,” it should take about two hours to get there.

Our advice: don't attempt to tackle the entire region in one visit, but choose a few areas to enjoy more deeply.

Special thanks goes to Alexandra from the social media team of the Region of Tuscany for answering a raft of questions and providing us with information about the region and its markets, festivals and art scene.

Note: In this post, we focus on northern Tuscany, the Valdichiana and Val d'Orcia regions in and around the towns of Montpulciano and Pienza, the setting of our wedding in 2000. We also spent a few days in the Maremma area of southern Tuscany, which we'll cover in a separate piece.

About Audrey Scott
Audrey Scott is a writer, storyteller, speaker and tourism development consultant. She aims to help turn people's fears into curiosity and connection. She harbors an obsession for artichokes and can bake a devastating pan of brownies. You can keep up with her adventures on Twitter, Facebook, and Instagram. And you can learn more about her on the About Page and on LinkedIn.

17 thoughts on “Tuscany in Autumn: From Hilltowns to Harvest”

  1. Wow, you got marry in Tuscany? That is so romantic, hahah kind of remind me the movie “Letters to Juliet”. You did an amazing jobs taking these photos. It brign me back lots of memory. Did you had the Florentine steak? haha

  2. There are a few place in the world that are hopelessly overdocumented and kind of cliched and you wonder, really, is there anything new to say about Italy, for example (I think of Hawaii as another such place) and yet, off we go, and we think, good lord, this place is STUNNING and the food it DELICIOUS and the Italian girls are so pretty wrapped around their handsome boyfriends on the Vespas… so yes, actually, I will sit through another slideshow or read another story about what some traveler ate because to be disappointed by Italy is to be half alive.

  3. Wonderful post. My family is considering a few weeks in Tuscany in a couple of years, though we were looking at June. Autumn sounds really nice.

  4. I probably sound like a broken record, but once again, beautiful photos. I was in Tuscany in March, but I’d love to see it in the fall.

  5. Love losing myself in your photos! Warm, beautiful, and definitely captured the sense of place.

    I definitely hear you on the winding roads!

  6. Audrey & Dan:
    The magic of Italy; the magic of Tuscany – it remains – confirmed by our recent visit to places where it all started ten years ago with your wedding and that special gathering of family and friends at Torre di Nano. Breathtaking is my description of that time as I watched that early evening golden glow roll across the vast fields and land on the back wall of Pienza. Capturing the moment is wonderful advice as is “roll with the punches”philosophy. We all did then and it guaranteed the fun, laughter and spontaneity that we enjoyed but that can be suffocated by perfect planning. Ten years later your desciptions instantly brought back fond memories and some unanticipated emotion. It was a delight. How could it not be. It was Italy; it was Tuscany.

    Your advice to deepen the experience by spending more time in fewer places is solid, but, alas, we failed. All of Tuscany and Umbria beckoned and we found ourselves dashing in all directions, almost unable to slow the pace that our aging systems were demanding. Perhaps next time.

    Overstimulated and overfed we brought our weary bodies home to our excited dog and cat and to some badly needed routine rest. But we know the pattern now. When we least expect it, music will occur or a brief travel section will appear on TV. We will look – we will laugh and almost in unison we will say “I miss Italy”

    It is a very diverse place of custom, culture, language (dialect) and food. It will never exhaust description. We are hooked. And it all began with family and friends and a wedding in Pienza. Thanks guys.

  7. @Michael: Even when we attempted to do as the Romans did — quite literally — we couldn’t drive quite fast enough to straighten out those Tuscan roads.

    @pam: Very well said. Though this time, I don’t know that we were treated to as many pretty Italian girls and handsome Italian men on Vespas as we would have liked.

    Like pearls to their grain of sand, clichés to their grain of truth.

    @sarah: We did get married in Tuscany. And it was romantic, in a hopeless, wide- and starry-eyed sort of way.

    Thank you for your compliments on the photos. But again, our hats go off to the people and to Mother Nature and the contours and shadows of the Tuscan landscape.

    Funny you ask about Florentine steak. When we were married, the man running the agriturismo where we were staying tried to convince us to eat 2 pounds of Florentine steak each. We negotiated him to 1 pound of steak each. It was still too much, as we allude to in this piece:

    @Keith: I’m sure summer in Tuscany is beautiful, particularly when the fields are green. But there’s something about the glow of Tuscany in autumn that does me right. Not to mention, once you get past summer, the crowds begin to drop off. If your family chooses Tuscany in late summer/early autumn, the first three weeks of September are ideal. The temperatures are still pretty warm, the sunflowers are still alive, though fading, the sun still shines (late September and early October bring on the rain, like clockwork) and all the September festivals (sagre) are in full swing.

    @Laura: I’m sure springtime in Tuscany is beautiful as well. Actually, just about any season. I actually harbor visions of holing up there in winter one of these years.

    @Sonya: As a place to kick off a life together, Tuscany certainly worked for us. It was also just as much how we kicked it off, as where:

    @Lola: Thanks! Yep, those winding roads — some dating to the Estruscans, others to the Romans — make for a bit of a real-life roller coaster. But it’s all worth it.

    @Don: Ah Tuscany and the wedding. One of those well-worn and deservedly dog-eared pages in the book of a life well-lived.

    Regarding the desire to chase it all at once, I think everyone reading and commenting can identify with that.

    Italy will always tug at the heart strings, even on the backs of the cheesiest of travel television shows. That’s just its way.

  8. What a romantic place to get married! I love the pictures, and now I want some cheese. 🙂 I have a friend who moved to Rome so I hope to visit Tuscany when I go visit him.

  9. @Jennifer: I don’t think we knew how romantic it would be.

    Those wheels of cheese were something else…both to ogle and to eat. Enjoy your visit to Rome (and Tuscany) and let us know if you’d like any other recommendations.

  10. Italy is a beautiful, special country and certainly a culture that cherishes its food. If you go to Tuscany you must try out their wine, red meat, pasta, pizza and gelato .

  11. Loved every word of this post…Tuscany was one of our favorite places to visit while in Italy. Your photos are beautiful and bring back so many memories. And I like your reference to the windy roads, they do take time to navigate!

  12. @Barbara: Glad this article and photos brought back great memories. This area is a truly beautiful part of the world, not just for physical beauty but for the culture and food. And yes, the windy roads do take time and patience 🙂

  13. Wow, such a great post. We have been to Milan, Rome, West of Sardinia and Sicily. After reading this post, Tuscany is our next Italian stop =) thanks

  14. @Adam: Although all the places you’ve been in Italy are pretty fabulous, I don’t think you’ll be disappointed by Tuscany when you go. Enjoy!!


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