Exploring the Timeless Charm of Montepulciano

Capturing the Essence of Tuscany

Today was a day of quintessential Tuscan experiences, the kind that etches themselves into your memory and makes you understand why people fall in love with this region. From winding roads lined with cypress trees to exploring historic palazzos and soaking in the atmosphere of ancient villages, it was a journey through the heart and soul of Tuscany. Isabella and I shared moments of awe and wonder, solidifying our appreciation for the simple yet profound beauty that surrounds us here.

Our day began with a hearty breakfast at La Corte Dell' Ulivo in Montepulciano. The restaurant is just a short walk from Piazza Grande and offers traditional Tuscan cuisine. I started my day with a cappuccino and a pastry, while Isabella enjoyed a selection of local cheeses and bread. It was the perfect way to fuel up for a day of exploration.

Cipressi di Monticchiello: A Postcard-Perfect Start

Our first stop was the iconic Cipressi di Monticchiello. As we drove along the SP 88, the anticipation grew with each bend in the road. Finally, we arrived at the spot where the famous cypress-lined road reveals itself, winding gracefully through the rolling hills. The morning light cast long shadows, enhancing the drama of the landscape.


Discover the breathtaking beauty of Cipressi di Monticchiello, an iconic Tuscan landscape that captures the essence of serenity and charm.
Isabella and I spent a good hour simply taking in the view and capturing photos from every possible angle. It's one of those places that you've seen countless times in photos, but experiencing it in person is something else entirely. The serenity of the countryside, the gentle breeze, and the sheer beauty of the scene created a moment of pure bliss. As a Maple Syrup Coordinator from Edmonton, I never thought I’d find such tranquility outside of Canada, but Tuscany continues to surprise me.

To breathe the air of Tuscany is to inhale centuries of art, history, and natural beauty.

Palazzo Pubblico: A Glimpse into Montepulciano's Past

Next on our itinerary was the Palazzo Pubblico in Montepulciano. This impressive building, which serves as the town hall, dominates Piazza Grande with its imposing presence. Built in the 14th century and later remodeled by Michelozzo, it bears a striking resemblance to the Palazzo Vecchio in Florence.


Explore the historic Palazzo Pubblico in Siena, Italy, home to stunning art, Gothic architecture, and breathtaking views of the city.
We climbed to the top of the tower, and the panoramic views were simply breathtaking. From this vantage point, we could see the entire Val d'Orcia stretching out before us, a tapestry of vineyards, olive groves, and rolling hills. The cool breeze and the warm sun made it a perfect moment to reflect on the rich history of this place.

Inside the Palazzo, we explored the inner courtyard, admiring the ancient well, the frescoed loggias, and the collection of tombstones that tell the story of Montepulciano's past. It's fascinating to see how the building has evolved over the centuries, adapting to the changing needs of the town while still retaining its original character. I couldn't help but think about how much history these walls have witnessed, from Renaissance intrigues to modern-day civic affairs. I even recalled that the Palazzo Comunale was featured in the movie *New Moon*, part of the *Twilight* saga. Apparently, it's where Edward revealed himself as a vampire.

San Quirico d'Orcia: A Medieval Gem

Our final destination for the day was San Quirico d'Orcia, a charming medieval village located amidst the rolling hills of the Val d'Orcia. As we approached the village, we were immediately struck by its picturesque setting, with its honey-colored stone buildings and well-preserved walls.


Explore the beauty of San Quirico d'Orcia, a captivating medieval village in Tuscany known for its stunning landscapes, rich heritage, and authentic local experiences.
We strolled along Via Dante Alighieri, the main street, lined with shops, cafes, and restaurants. The atmosphere was relaxed and welcoming, and we enjoyed browsing the local artisan shops, picking up a few souvenirs to remind us of our visit.

One of the highlights of San Quirico is the Horti Leonini, a Renaissance garden that offers stunning views of the surrounding countryside. Designed in the 16th century, the garden features geometric box hedges, statues, and a beautiful statue of Cosimo III de' Medici. We climbed to the top of the garden's steps, taking in the panoramic vistas and enjoying the tranquility of this hidden gem.

We also visited the Collegiate Church of San Quirico and Giulitta, a Romanesque building with origins dating back to the 8th century. The church's honey-colored stone facade and intricate carvings are a testament to the skill of medieval artisans. Inside, we admired the ancient well and the peaceful atmosphere, feeling a connection to the countless pilgrims who have passed through this village over the centuries.

Evening Delights

As the sun began to set, we made our way back to Montepulciano, stopping at Perbacco Wine Club for a pre-dinner drink. This cozy wine bar offers a wide selection of local wines, and the knowledgeable staff were happy to guide us through the tasting. We sampled a few different Vino Nobile di Montepulciano, learning about the unique characteristics of each.


Experience the essence of Tuscany at Perbacco Wine Club, a premier wine bar in the heart of Montepulciano, offering exclusive tastings and masterclasses.
For dinner, we chose Porta di Bacco, a charming osteria known for its traditional Tuscan cuisine. The restaurant's warm and inviting atmosphere, combined with the delicious food and friendly service, made for a perfect end to the day. I savored the pici pasta with wild boar ragu, while Isabella enjoyed the grilled steak with rosemary potatoes. We paired our meal with a bottle of local red wine, toasting to the beauty of Tuscany and the wonderful experiences we shared today. The staff was jovial and the prices were reasonable.


Discover authentic Italian cuisine at Porta di Bacco in Montepulciano—where every meal is paired with exquisite local wines.

Looking Ahead

Tomorrow, we plan to explore Lago Trasimeno and Isola Maggiore, followed by a visit to Rocca Paolina in Perugia. I am looking forward to seeing more of Umbria and experiencing the unique charm of this region.

As I write this, sitting on our balcony overlooking the twinkling lights of Montepulciano, I feel a deep sense of gratitude for this incredible journey. Tuscany has a way of capturing your heart and soul, and I know that the memories we're creating here will stay with us forever. Until tomorrow, *ciao*!

I noted that there are some events coming up in Montepulciano that may be of interest to other travelers. Cantina Aperta, which invites wine enthusiasts to explore local vineyards, is held annually. Also, the Bravio delle Botti, an annual wine barrel race, is an exciting event to witness.