Approaching Montepulciano is like watching a postcard come to life. As the rolling Tuscan hills give way to a skyline crowned with medieval towers and rooftops, it’s impossible not to feel a sense of anticipation. For us, Montepulciano is more than just a destination—it’s a town that holds a special place in our hearts thanks to its rich history, stunning vistas, and, of course, its wine.
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This picturesque hill town, nestled in the Siena province of Tuscany, is famous for its Vino Nobile di Montepulciano, a wine celebrated worldwide for its elegance and depth. This delightful grape variety brings a unique charm to Montepulciano’s wines, making them a must-try for any wine enthusiast.
A Perfect Blend of Old and New
Montepulciano is a town of contrasts: ancient history meets modern life. Spanning 64 square miles and perched at an elevation of 2,000 feet, Montepulciano offers sweeping views of the Val d’Orcia.
The streets are a feast for the senses. Quaint shops line the cobblestones, offering everything from artisanal cheeses to beautifully crafted ceramics. I am particularly fond of and collect oversized dishtowels sold at many shops. These dishtowels are practical souvenirs—perfect for baking bread, drying pasta, and adding a touch of Tuscany to your kitchen.
What Makes Montepulciano Special?
This charming town is celebrated for its culinary and cultural treasures. Here’s a closer look at what makes Montepulciano so unforgettable:
- The Wine: Montepulciano is synonymous with Vino Nobile di Montepulciano, a wine prized since the 8th century. With its velvety texture and complex flavors, it’s a delight to sip while overlooking the rolling vineyards where it was born. Many wineries offer tastings, and visiting a local cantina is a highlight of any trip.
- The Views: From the town’s highest points, you can gazeat the iconic Tuscan landscape—a patchwork of vineyards, olive groves, and cypress-lined roads.
What is the Town Known For?
The town is renowned for its pork, cheese, pecorino cheese, pici pasta, lentils, honey, and Vino Nobile wine.
Pici are thick, hand-rolled pasta, like fat spaghetti. It originated in the Montalcino area. The dough is typically made from flour and water only.
The Beautiful Town
Photography enthusiasts will love capturing the town’s details—from weathered wooden doors to vibrant flower boxes perched on window sills. I’m always drawn to the little nooks and crannies, those quiet spots where time seems to stand still.
Be prepared for some climbing; the town is perched on a hill, after all. But the effort is well worth it. The views from Montepulciano are nothing short of spectacular, with the Tuscan countryside stretching out in every direction.
Here is a view of the main piazza. You have to climb a pretty steep hill to get to it!
Wandering through Montepulciano feels like stepping into a museum. The cobblestone streets wind through a labyrinth of alleyways, with each turn revealing something new: a charming café, a hidden courtyard, or a shop filled with treasures.
History
According to legend, the Etruscans founded the town around the 3rd or 4th century BC. The town’s loyalty to Florence shaped much of its destiny. In the 12th century, Montepulciano found itself in constant conflict with the Republic of Siena but managed to fend off attacks with the help of allies like Perugia and Orvieto. After Florence conquered Siena in 1559, Montepulciano’s strategic importance declined, but its artistic and architectural heritage flourished. The Medici family ruled the town from 1609 to 1636, commissioning stunning churches and palaces that still stand today.
A Stroll Through Town
Here is a view of some of the streets and alleyways. I also included a few doors that are my love and passion for photography. You can see my other post with pictures of wooden doors.
As we walked, the small nooks and crannies that lead from one street up or down to another are such a treat. Yes, it requires climbing but the little shortcut paths are quaint and full of fun. You don’t know when exploring exactly where you will emerge but it’s fun to guess.
We love this town. It truly has charm and is exactly what you would expect in the Tuscan region. In the picture to the right below, I caught a little cat stretching. We spent about 10 minutes watching him chase a small rodent and then gave up and stretched. It was cheap entertainment for the day!
Both these books beautifully capture the essence of Italy, its people, and the strong sense of community that defines life in small Italian towns. With lyrical prose and reflections, Ilene & Gary invite readers to accompany them on a journey of self-discovery and transformation in the heart of Tuscany.
Both books have won the Reader Ready “Recommended Read Award”
Festivals and Events
If you plan a visit, try to time it with one of Montepulciano’s vibrant festivals. The most famous is the Bravio delle Botti, held on the last Sunday of August. This thrilling event sees teams from different districts rolling enormous wine barrels through the town’s steep streets. The race dates back to the 14th century, accompanied by parades, costumes, and plenty of celebratory spirit. You can find more information here at one of my favorite sites for event discoveries in Tuscany, Discover Tuscany.
Wine Tasting
We went to a wine tasting while we were in Montepulciano. It was down in a cave under the street. The wine was excellent and we stumbled upon them cleaning the barrels. All of a sudden I see a blue hand! I didn’t know they scrape the inside of the barrel to clean them for the next use. Not a job I would want to be a little claustrophobic!
Beyond the Town: What to See Nearby
Montepulciano is also a great base for exploring the surrounding region. Nearby attractions include:
- San Biagio Church: This stunning Renaissance church is a masterpiece of harmony and symmetry just outside the town.
- Pienza: This UNESCO World Heritage Site is a short drive away, known as the “ideal city of the Renaissance.”
- Val d’Orcia: This iconic landscape has inspired countless artists and photographers with its rolling hills and picturesque farms. And don’t forget the little single room church!
In Closing – Final Thoughts
Montepulciano is a town that stays with you long after you leave. Whether you’re sipping a glass of Vino Nobile in a sun-dappled piazza, exploring the cobblestone streets, or soaking in the breathtaking views, Montepulciano offers a quintessential Tuscan experience.
Make time to visit this enchanting hill town—you won’t just fall in love with Montepulciano; you’ll find a piece of Tuscany to carry in your heart forever.
