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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.”
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For the ultimate vantage point to take in the entire Val d’Orcia region, Monteverdi Tuscany commands the most iconic views and stands as nothing short of a design lover’s dream, a boutique hotel that masterfully fuses rustic stonework with contemporary art. I fell in love with its serenity, from the perfect, crisp C&C Milano handmade linens sheets to the Santa Maria Novella bath amenities that make every moment feel like pure indulgence. Oreade offers an intimate fine dining experience for 14 guests every evening, with exquisite dishes prepared by executive chef Riccardo Bacciottini. The restaurant design is rooted in local Tuscan culture, emphasizing natural materials and aligning with the chef’s passion for sustainability, storytelling, and foraging locally sourced ingredients—making it the hottest new reservation in the area, paired beautifully with under-the-radar wines like Cantina Cignus et Leonis S uthi Usil Grand Cru Metodo Classico, an exceptional sparkling Tuscan wine.
In recent years, Val d’Orcia has evolved to boast a new wave of design-forward luxury hotels and boutique stays that blend seamlessly into its landscape. To reach this serene haven, I always recommend flying into Rome and stay at Hotel d’Inghilterra Roma to acclimate, and then on the way back, drive to Florence and stay at one of Betty Soldi and Matteo Perduca’s dreamy hotels (Ad Astra is always my number one, but their newest, Stella d’Italia, is in the heart of it all but still feels like countryside). You must rent a car: Sixt is my trusted source for navigating those winding roads that unfold into vistas so breathtaking, they feel like driving straight into a postcard.
Here’s everything you need to know for each of Val d’Orcia’s five municipalities:
Montalcino
Beyond its legendary Brunello wine, Montalcino’s magic extends from its 14th-century fortress to the tranquil, vine-draped village of Sant’Angelo in Colle and the serene, Romanesque masterpiece of the Abbey of Sant’Antimo in Castelnuovo dell’Abate. For an immersive vineyard experience, Mastrojanni offers stylish, contemporary suites and a gorgeous pool overlooking the Orcia valley—a quintessential stay for any serious Brunello aficionado seeking to sleep amid the very vines that produce it. Another hidden gem, Castello di Velona, offers a delightful stay, tucked behind ancient gates on the commune’s winding roads.
Boccon DiVino stands as a venerable institution, serving elevated Tuscan classics from a terrace that perfectly frames the rolling vineyards, while within the grandeur of Rosewood Rosewood Castiglion del Bosco, Campo del Drago offers a Michelin-starred dining experience where organic ingredients and exquisite Brunello pairings are the norm. For a hip, modern vibe that feels like a chic beach club amidst the vines, don’t miss Vineria Aperta—a wine bar boasting over 1,500 labels, including their own standout wines from the farm. And if you’re within the Montalcino walls, book a table at Osteria di Porta al Cassero for refined Tuscan cuisine with breathtaking valley panoramas and savor an espresso at Caffè Fiaschetteria Italiana afterwards.
This commune is also a true cradle of sustainable wine production: explore Col d’Orcia, Tuscany’s largest organic estate; discover Podere Le Ripi, a biodynamic trailblazer; and be sure to experience Donatella Cinelli Colombini’s all-women-run winery, showcasing female leadership in wine with tastings—and don’t miss her Cenerentola (Cinderella) wine, your chance to give Orcia DOC wines a proper chance. A must-see is Poggio di Sotto, the cult estate known for benchmark, classical Brunello with an astonishing 182 different Sangiovese clones planted randomly throughout their vineyards, creating a true monovarietal “field blend” that produces wines of radical elegance and finesse. For historic prestige, Il Poggione stands as one of the oldest and most respected estates, while Stella di Campalto represents the new guard—a tiny cult producer run by a passionate woman winemaker whose natural approach yields some of the most sought-after bottles in all of Tuscany.
Beyond wine, stop by FradO for handmade leather goods and the stunning Montalcino 564 Di Massimo Gorelli S.n.c., hunt for treasures at the vibrant Saturday market, and explore artisanal boutiques tucked into ancient stone buildings. The imposing fortress offers sweeping Val d’Orcia views and houses the Civic and Diocesan Museum with masterpieces by Simone Martini and Giambologna.
Pienza
Pienza beckons as the “Ideal City of the Renaissance” with its perfectly proportioned piazzas and the irresistible allure of its famed pecorino (seriously, the city smells of deliciously stinky cheese in the best way possible), a commune that also encompasses the raw, authentic charm of the medieval hamlet of Monticchiello.
For accommodation that feels like a chic home away from home, La Bandita Townhouse offers a distinctive experience: a Renaissance convent brilliantly reimagined as a boutique hotel, where owner John Voigtmann—a former Sony executive who fell in love with Pienza and now lives in the walled city—and his ex-wife, writer Ondine Cohane, created an intriguing space filled with music memorabilia, an honor bar, and daily complimentary aperitivo that fosters a “staying with friends” ambiance. If you’re lucky, find his wire-haired dachshund, Giulietta, playing her never-ending game of ball at the hotel’s outdoor courtyard. (You can also quickly get lost with all the delicious bottles of wine from the region at the restaurant with the sommelier.) For two options not inside the walls, consider L’Olmo—an intimate retreat amidst ancient cypress trees in a beautifully converted 17th-century farmhouse—and Casa Newton, a top pick from the Mr Mrs Smith team.
For eats, The Townhouse Café, under Chef David Mangan, serves gourmet comfort food including a truly legendary burger (so legendary that esteemed Hotel Il Pellicano, in Porto Ercole, now offers it), while La Terrazza della Val d’Orcia, owned by the founders of the Brunello di Montalcino Consortium, offers seasonal Tuscan classics with breathtaking valley views. For a true farm-to-table experience, Podere Il Casale allows you to savor delicious meals with unbeatable views and witness cheese being made from their own sheep, still produced organically in the age-old way. As dusk settles, Idyllium transforms into the go-to spot for sunset aperitivo, and no visit is complete without Buon Gusto Gelateria. Owner Nicola Scgarbi, a former chef, also has locations in San Quirico and Montepulciano, and the spot features inventive, all-natural flavors like summer sheep’s ricotta and blueberry or the decadent sbagliato stracciatella dipped fresh into a cascading chocolate fountain.
Beyond culinary pleasures, the Renaissance streets feature artisan boutiques, pecorino from specialized shops (OFFICINE 904 is a must for posh leather bags and accessories), and so much more. Visit Palazzo Piccolomini for glimpses into 15th-century aristocratic life and breathtaking views with a stunning garden that overlooks the region.
For a modern dip into the wine world, adventure out to Fabbrica Pienza, a winery and cultural hub seamlessly blending art, architecture, and organic production—they’re bucking tradition with a pet nat and wines beyond the typical regional offerings, plus stunning art installations including colorful sculpture made of painting stones by Ugo Rondinone.
In nearby Monticchiello, Ristorante Daria offers an elegant atmosphere on the main street with tradition meeting innovation, while Osteria La Porta serves exceptional Tuscan cuisine on a terrace with stunning views of Pienza and the entire Val d’Orcia—grab an outside table for the best experience. And don’t miss Teatro Povero, a social and cultural project dating back to the 1960s that stages local theater productions.
San Quirico d’Orcia
Maybe I’m biased, but San Quirico d’Orcia is my favorite commune—a beautifully preserved medieval walled town on the ancient Via Francigena, renowned for its exquisite Horti Leonini gardens, Collegiata church, and the unique thermal village of Bagno Vignoni, where the main square is an actual ancient thermal pool.
For a truly unique stay, Hotel La Posta in Bagno Vignoni is like euphoria—you enter the door and enter a world of serenity, where you can bask by the thermal pools and have a leisurely lunch at Il Chiosco (arguably the best club sandwich in all of Tuscany), providing historic charm directly in the village’s heart and allowing guests to effortlessly transition from elegant rooms to soak in the very same ancient Roman thermal pools that have drawn visitors for centuries.
In Bagno Vignoni, Il Barrino beckons for perfect under the Tuscan sun cocktails and a coveted front-row seat to the village’s steaming piazza pool. La Bottega di Cacio remains one of my personal best-kept secrets—this family-run delicatessen invites you to select exquisite oil-soaked delights, local cheeses, and cured meats, all perfectly paired with hand-selected local wine to savor al fresco amidst the sun-drenched piazza. La Rocca restaurant offers large windows with charming views of the pools and lush Tuscan garden—a step back in time where wait staff wear fluffy oversized red bows and formal attire, where you can go super traditional Tuscan or try something modern, and where every meal should end with proper crêpe tableside service à la flame.
Note: If you’re staying in an agriturismo, it’s highly suggested to visit La Bottega delle Carni Srl—the best butcher in the region hands down—and grab a bistecca alla Fiorentina to cook for a feast.
Beyond the thermal delights, visit the Chapel of the Madonna di Vitaleta—this UNESCO chapel of late Renaissance origin offers single nave beauty and commanding views of the entire Val d’Orcia region. Do the art and history tour with Serena Tarquin at Vitaleta, a sommelier who will teach you so much about the region, including that Moscadello di Montalcino—a sweet white wine—was actually pre-Brunello dominance until the mid-19th century. It’s best to go for sunset and then open a bottle or two, sit back with local meats and cheeses, and take it all in.
Don’t miss the charming shops along the medieval streets of San Quirico, either: Manufacto Store offers handmade objects of refined design that resonate with stories and craftsmanship, while Val d’O la Vineria Letteraria provides a unique literary wine experience. The town also comes alive during community festivals throughout the year, celebrating everything from harvest season to medieval traditions. After shopping, experience Antica Trattoria Toscana Al Vecchio Forno for its wood-fired specialties and convivial service that epitomizes genuine Tuscan hospitality.
Castiglione d’Orcia
Beyond the postcard-perfect vistas, the commune of Castiglione d’Orcia offers a less-trodden Val d’Orcia, inviting exploration from its majestic medieval fortresses and charming hidden hamlets like Vivo d’Orcia (whose core is the ancient Eremo Camaldolese monastery) to the ethereal, milky-white thermal springs of Bagni San Filippo—trust me when I say these thermal springs are unlike anything you’ve experienced. For a touch of fresh, understated luxury, book a room at Locanda Tuscany offers countryside tranquility just a short drive to the fairytale village of Rocca d’Orcia, where their newly renovated sister property, Rocco d’Orcia Suites and Villas, provides a minimalistic stay in the heart of the village—and a pool that offers some of the best views of Val d’Orcia.
For those nights when only hearty, rustic Tuscan fare will do, Il Cerchio Delle Streghe delivers the finest, most perfectly cooked bistecca alla Fiorentina with panoramic views that stretch endlessly to the horizon, while Osteria Santa Caterina (a few miles in the country) is perfect for a leisurely lunch with friends—especially during porcini season from late summer through the fall. Rocca d’Orcia Grill is an absolute must, reached by a charming walk down into the cobblestone village streets—it’s like walking around in a fairytale. It’s wise to have a drink at Enoteca Dell’Orcia first, then stroll to dinner.
Radicofani
Dramatically perched atop a volcanic outcrop at Val d’Orcia’s southern edge, Radicofani feels refreshingly untouched—a fortified medieval time capsule that somehow escaped the usual tourist throngs. The star here is the imposing Fortezza di Radicofani, where climbing to the summit rewards you with sweeping 360-degree views across the entire valley toward distant Monte Amiata. It’s the kind of panorama that stops you cold.
For dining, Restaurant Fortezza serves exceptional pici ragu with those million-dollar fortress views, while intimate Trattoria La Grotta offers traditional cuisine in a cozy stone-walled setting that feels authentically local. Don’t miss the mysterious Bosco Isabella—a 19th-century romantic garden filled with exotic plants and intriguing Masonic symbols, including an enigmatic stone pyramid. The 13th-century Chiesa di San Pietro showcases exquisite terracotta and wooden artworks, including masterpieces by Francesco di Valdambrino. Radicofani is where medieval Tuscany reveals its most dramatic, unvarnished self.