Tuscany’s sunlit hills have long called to me, but it was during my extended time at Podere Aiole—a newly restored agriturismo in Castiglione d’Orcia—that I truly fell for the quiet allure of the Val d’Orcia. This isn’t the Tuscany you think you know; this region, nestled in southern Tuscany within the province of Siena, stretches from the Orcia River southward toward the border with Grosseto. Here, winding roads unfold into vistas so breathtaking, they feel like driving straight into the Emerald City from the Wizard of Oz, its timeless beauty inspiring everyone from Renaissance artists to masters of the silver screen.

What truly sets Val d’Orcia apart is its untouched authenticity—and its extraordinary culinary heritage. This is the land of handmade pici pasta, liquid-gold olive oil from producers like Chiarentana, and pecorino so sublime it perfumes entire villages. The world-famous Brunello wine pairs perfectly with cinta senese cured meats, while a slow morning at a cafe in the quaint Castiglione d’Orcia, savoring an espresso and pistachio-filled cornetto, epitomizes what la dolce vita is all about. Beyond the obvious—unforgettable wine and amazing gastronomy—you’ll also discover charming antique shops, elevated cheese purveyors, hidden art galleries, and even a few fantastic cocktail bars.

“My love affair with the Val d’Orcia region began in 2003 when I visited Tuscany for a birthday celebration,” says Michael Cioffi, founder and owner of Monteverdi Tuscany. “A friend suggested a hike up to a hilltop village, Castiglioncello del Trinoro. Upon reaching the village, I was awestruck by the incomparable beauty of the surrounding landscape and instantly felt as though I had stepped out of time. That timelessness was so captivating that it led me to buy, preserve and restore one building, which grew into many more, creating Monteverdi Tuscany.”