A Week in Val d’Orcia, Tuscany: A Journey Through Rolling Hills and Timeless Villages
Val d’Orcia, a UNESCO World Heritage site, is a stunning region in Tuscany known for its rolling hills, cypress-lined roads, and medieval villages. This picturesque landscape has inspired countless artists and is a testament to the harmonious relationship between humans and nature. The region is also famous for its exquisite wines, such as Brunello di Montalcino and Vino Nobile di Montepulciano, making it a paradise for wine enthusiasts.
Beyond its natural beauty, Val d’Orcia is steeped in history, with towns like Pienza, Montepulciano, and Montalcino offering a glimpse into the past. These towns boast Renaissance architecture, charming piazzas, and vibrant local markets. Visitors can explore ancient fortresses, sample local delicacies, and immerse themselves in the rich cultural heritage of the region.
Travelers to Val d’Orcia can expect a delightful blend of relaxation and adventure. Whether you're savoring a glass of wine at a local vineyard, wandering through cobblestone streets, or enjoying a traditional Tuscan meal, this itinerary promises an unforgettable experience. Be sure to pack comfortable shoes, a camera, and an appetite for discovery!
Pienza
Pienza, often referred to as the "Ideal City," is a Renaissance gem nestled in the heart of Val d’Orcia. Designed by Pope Pius II in the 15th century, Pienza is a masterpiece of urban planning, with its harmonious streets and stunning views of the surrounding countryside. The town is famous for its pecorino cheese, a must-try for any visitor.
Morning: Begin your journey in Pienza with a leisurely stroll through its charming streets. Visit the Piazza Pio II, the town's main square, and admire the stunning architecture of the Pienza Cathedral and Palazzo Piccolomini. For breakfast, stop by Bar Il Casello for a cappuccino and a freshly baked pastry.
Afternoon: Explore the Pienza Cheese Festival, where you can sample and purchase the town's renowned pecorino cheese. For lunch, head to Trattoria Latte di Luna, known for its delicious pici pasta and warm hospitality. Afterward, take a scenic walk along the town's walls for breathtaking views of the Val d’Orcia landscape.
Evening: Enjoy a traditional Tuscan dinner at Osteria Sette di Vino, where you can savor local dishes paired with a glass of Vino Nobile di Montepulciano. After dinner, take a leisurely walk through the town's illuminated streets, soaking in the serene atmosphere.
For accommodations, consider staying at a charming local property through VRBO or Hotels.com.
Montepulciano
Montepulciano, a hilltop town renowned for its wine, offers a perfect blend of history, culture, and gastronomy. The town's medieval and Renaissance architecture, combined with its vibrant wine culture, make it a must-visit destination in Val d’Orcia.
Morning: Start your day with a visit to the Piazza Grande, Montepulciano's main square, and explore the Palazzo Comunale and the Duomo. For breakfast, enjoy a coffee and pastry at Caffè Poliziano, a historic café with stunning views.
Afternoon: Embark on a wine-tasting tour at one of Montepulciano's renowned wineries. Consider the Small-Group Wine Tasting Experience in the Tuscan Countryside for an immersive experience.

Evening: After a day of exploration, unwind with a glass of Vino Nobile at Enoteca La Dolce Vita. For dinner, savor a meal at Ristorante La Grotta, located near the Church of San Biagio, offering exquisite Tuscan cuisine in a romantic setting.
Stay overnight in Montepulciano by booking through VRBO or Hotels.com.
Montalcino
Montalcino, the birthplace of the prestigious Brunello wine, is a charming town surrounded by vineyards and olive groves. Its medieval fortress and panoramic views make it a captivating destination for travelers.
Morning: Begin your day with a visit to the Montalcino Fortress, where you can enjoy panoramic views of the surrounding countryside. For breakfast, stop by Caffè Fiaschetteria Italiana for a cappuccino and a slice of torta della nonna.
Afternoon: Explore the town's wine culture with a visit to a local winery. Consider the Wine Safaris: Chianti, Val d'Orcia, Brunello Wine Tours & Lunch for an unforgettable experience.

Evening: Conclude your day with a visit to the Abbey of Sant'Antimo, a beautiful Romanesque church located just outside Montalcino. For dinner, indulge in a culinary experience at Ristorante Il Leccio, known for its creative take on traditional Tuscan cuisine.
Book your stay in Montalcino through VRBO or Hotels.com.
As your week in Val d’Orcia comes to a close, you'll leave with memories of breathtaking landscapes, exquisite wines, and the warm hospitality of Tuscany. This journey through Pienza, Montepulciano, and Montalcino offers a perfect blend of history, culture, and gastronomy, ensuring an unforgettable experience in one of Italy's most enchanting regions.