If you love wine, history, and charming Italian streets that seem like they were plucked straight out of a painting, Montepulciano is your dream destination. Nestled in Tuscany, this hilltop town is famous for its Vino Nobile di Montepulciano, an exquisite red wine with centuries of tradition. But Montepulciano is not just about sipping wine; it’s about savoring the culture, exploring the architecture, meeting passionate winemakers, and walking through streets that whisper stories of the past.

From my own personal experience, Montepulciano has this magical way of making every wine tasting feel personal, every sunset unforgettable, and every cobblestone street worth wandering. If you’re planning a trip here or simply want to live vicariously through someone who has, let me take you through ten things you truly need to see and do as a wine lover in Montepulciano.

1. Tour the Historic Cellars of Montepulciano

Montepulciano isn’t just about drinking wine; it’s about understanding it. One of the best ways to do this is by visiting the town’s historic cellars. Many of these cellars are carved directly into the limestone beneath the town, some dating back hundreds of years. Walking down these cool, dimly lit tunnels, you’ll see barrels stacked like ancient treasure and learn about the meticulous process of aging Vino Nobile.

From my own personal experience, the best part isn’t just the wine—it’s listening to the winemakers share stories about the families who have been making this wine for generations. Some even let you try small samples directly from the barrel. There’s something about drinking wine in the place where it’s been born that feels extraordinary.

2. Stroll Through Piazza Grande

No visit to Montepulciano is complete without a walk through Piazza Grande, the town’s main square. Surrounded by Renaissance architecture, including the impressive Palazzo Comunale, this square is where locals gather, artists perform, and wine lovers soak in the atmosphere before heading to the tastings.

Grab a gelato or a cappuccino and just watch life happen around you. The sense of history here is palpable—every building has a story, every corner a secret. If you’re feeling adventurous, climb the Palazzo Comunale tower. The view of the rolling Tuscan hills covered in vineyards is breathtaking. You might even feel like a Renaissance lord surveying your domain—but with better shoes and less responsibility.

3. Visit Cantina Contucci

Cantina Contucci is one of Montepulciano’s oldest and most celebrated wineries, with a lineage going back to the 18th century. Here, wine isn’t just a product; it’s a family legacy. A tour of Cantina Contucci includes walking through centuries-old cellars, learning about traditional winemaking techniques, and of course, sampling their exceptional Vino Nobile di Montepulciano.

From my own personal experience, their guided tasting is one of the most engaging in town. You don’t just taste wine; you taste history, tradition, and passion poured into every bottle. And if you’re lucky, the staff might share a funny anecdote about a particularly stubborn barrel that refused to cooperate for decades.

4. Explore the Wine Museum of Montepulciano

For a more structured dive into the history of wine, the Wine Museum of Montepulciano is a must-see. This museum showcases ancient winemaking tools, traditional fermentation techniques, and detailed explanations of the Vino Nobile di Montepulciano production process. It’s both educational and visually stunning.

Walking through the museum, you’ll find yourself imagining the vintners of the past, carefully tending to their vines with the same dedication you see today. It’s a reminder that Montepulciano’s wine culture is not a modern invention—it’s a centuries-old tradition, perfected over generations.

5. Participate in a Wine Tasting Workshop

Tasting wine is fun, but understanding wine is unforgettable. Montepulciano offers several wine tasting workshops where you learn to identify aromas, pair wines with food, and even understand the subtle differences between vintages. These workshops are hands-on, making them perfect for both novices and seasoned wine lovers.

From my own personal experience, a workshop where I learned to distinguish subtle notes of cherry, leather, and spice in Vino Nobile changed the way I appreciate wine forever. You don’t just drink it—you understand it, and that makes every sip more meaningful. Plus, these sessions are often accompanied by a generous spread of local cheeses and meats, making it a deliciously immersive experience.

6. Walk the Wine Road of Montepulciano

For those who love scenery as much as wine, the Wine Road (Strada del Vino Nobile) is a must. This route winds through the Tuscan countryside, passing rolling hills, lush vineyards, and charming farmhouses. Along the way, you can stop at small, family-run wineries for tastings that are less commercial and more personal.

It’s an experience that combines physical activity with indulgence. Imagine walking through vineyards with a glass in hand, the sun on your face, and the smell of grapes in the air—it’s practically a scene from a movie, only better because it’s real.

7. Discover Local Artisan Shops

Montepulciano isn’t just about wine; it’s about the full sensory experience. While wandering its narrow streets, take the time to visit local artisan shops. From handcrafted leather goods to ceramics inspired by the region, these stores showcase the creativity and tradition of Tuscan artisans.

Some of these shops even offer small wine pairings with local delicacies, allowing you to taste the town while you shop. Based on my overall experience, these little detours often become highlights, giving you a richer, more personal connection to Montepulciano than any guidebook ever could.

8. Enjoy a Sunset from the City Walls

Montepulciano’s location atop a hill provides some of the most stunning views in Tuscany. For wine lovers, watching the sun set over vineyards while sipping a local vintage is nothing short of magical. The city walls provide perfect vantage points for photography, quiet reflection, or just soaking in the peaceful atmosphere.

Trust me, you’ll want to schedule your wine tastings and strolls around sunset. The warm hues of the sky, the silhouette of the town, and the rolling vineyards below create a scene that feels almost surreal. It’s a moment that makes you appreciate why Montepulciano has inspired poets, painters, and wine enthusiasts for centuries.

9. Attend a Seasonal Wine Festival

Montepulciano comes alive during its seasonal wine festivals, especially during the Vino Nobile Wine Festival. These events are a celebration of local culture, featuring tastings, food pairings, music, and sometimes theatrical performances. It’s a festive way to experience the town while indulging in its main attraction—wine.

From my own personal experience, attending one of these festivals felt like being part of a giant family reunion. The locals are friendly, passionate, and love sharing their wine heritage with visitors. You’ll leave not only with a fuller glass but also with a deeper appreciation for Montepulciano’s unique wine culture.

10. Savor Local Cuisine with Wine Pairing

Finally, no visit to Montepulciano is complete without indulging in local cuisine. Tuscan dishes, like pici pasta, wild boar ragù, and pecorino cheese, pair beautifully with Vino Nobile. Many restaurants in town offer curated wine pairings, making your meal a true gastronomic experience.

Based on my overall experience, the best way to enjoy Montepulciano is to combine wine and food in every meal. A perfectly paired dish elevates both the wine and the food, and every bite becomes a celebration. Don’t rush it; take your time, savor each flavor, and enjoy the rhythm of Tuscan dining.


Montepulciano is more than a town; it’s an experience. From wandering historic streets and tasting centuries-old wines to watching sunsets over rolling vineyards, it’s a place that stays with you long after you’ve left. If you’re a wine lover, it’s a destination that satisfies all senses—sight, smell, taste, and even touch, as you feel the history beneath your feet.

Exploring Montepulciano is like opening a bottle of Vino Nobile: rich, complex, and unforgettable. Each of these ten experiences offers a unique perspective on the town and its wine, and together, they create a journey you’ll truly love. So pack your curiosity, your love of wine, and a comfortable pair of shoes, because Montepulciano is waiting—and it’s worth every sip and every step.