Wine Tasting in Montepulciano’s Historic Center

Montepulciano is a stunning hillside town in Southern Tuscany, not far from Siena and easy to reach by car when traveling between Florence and Rome.

The town has Etruscan origins, and the medieval center boasts beautifully preserved Renaissance palaces, ancient churches, wine cellars, quiet side streets, and unmatched panoramic viewpoints over the nearby valleys. Montepulciano offers easy access to the towns in its own Val di Chiana, such as Siena, Cortona, and Chianciano Terme and in the nearby Val d’Orcia—Pienza, Bagno Vignone, Montalcino, and Radicofani.

I recommend that you have a car if you’re visiting Montepulciano. The historic center is a 20-minute bus ride from the Montepulciano train station and with all of the towns to explore in Southern Tuscany, a car will make that more possible. I rented one at the Florence airport and drove to Montepulciano, but you could also rent one from Rome. According to my research, there are no car rental agencies in town or near the train station. You can find my tips for renting a car in Italy here.

Perhaps the biggest draw to Montepulciano is its wine--Vino Nobile di Montepulciano. To be labeled as such, the wine must be produced in the defined geographical area surrounding Montepulciano and must be at least 70% Sangiovese.

One of the things I love about Montepulciano is the tasting opportunities within the historic center. Especially if you are traveling solo and want to make a day out of tastings, to do so with a car may not allow you to drive back safely or you would need to arrange transportation or a group experience ahead of time. Those are good options, but if you want to be a bit more spontaneous, you can leave your car parked and “walk and taste” instead.

These are my recommendations for wine tasting in Montepulciano’s historic center.

1. Cantina De’Ricci

Palazzo Ricci is an impressive Renaissance building in historic Montepulciano and serves as the entrance to Cantina De’Ricci, which is owned by the Trabalzini family.

I joined a group tour that ended with a tasting of either three or six wines (go for six if you've come all this way!) after visiting and learning the history of one of the most impressive cellars I've seen. With the long aisles and arches, it's as though you're walking through an underground cathedral. The photos will not do it justice. This is a place you have to see in person to fully appreciate.⁠

To schedule a tour and tasting, contact De'Ricci via their website.

The tour + tasting lasted about 1.5 hours, and the entrance is in the historic center on Via Ricci (Via di Ricci, 11, Montepulciano).

2. Cantina Chiacchiera

You can visit the vineyards and cellars of this family winery in Cervognano, southeast of Montepulciano, where Emanuela Mancianti, the winery’s founder, is heavily involved in all aspects of the business. Or, enjoy a wine tasting and food at the family’s wine stop in the historic center, as I did for aperitivo.

The staff was cheerful and helpful. I did not order food since I was on my way to dinner, but the shop receives great reviews for their offerings.

“Chiacchiera” means “chatterbox” in Italian, and is the nickname for Emanuela’s father Mario.

You can find the wine shop at: Via di Voltaia Nel Corso, 50, Montepulciano

The winery is located at: Via di Poggio Golo, 12, 53045, Cervognano

You can find more contact info on their website here.

3. Talosa

The Jacorossi family has run Talosa since the 1970s. Their vineyards are located in the hills surrounding Montepulciano, but their main cellar is in the historic center, located under Piazza Grande.

The “basement” of two of the town’s oldest buildings, Palazzo Tarugi and Palazzo Sinatti, serve as Talosa’s cellar. You can walk through the cellar on your own, without a reservation, by visiting the wine shop in Via Talosa, 8, or you can arrange a guided tour of the cellar and a wine tasting at the end.

You can find more details on their website.

4. E Lucevan Le Stelle

The name of the charming wine bar in Piazza di San Francesco translates to “And the Stars Were Shining.” How romantic! Like the ambiance inside. The back walls are lined with bottles of wine, mostly local. Soft light filters in through the large windows. The welcoming patio was not open on the chilly, rainy evenings when I was there, but it would be the perfect aperitivo spot overlooking Piazza di San Francesco and its unmatched view of the sunset over the valley.

The bistro has a feature I hardly encounter in Italy—bar seating. Perfect for solo travelers!

Aside from the impressive wine list and welcoming vibe, E Lucevan Le Stelle offers a small menu of local dishes. I opted for pici (think: fat spaghetti), one of the local pasta types, with a beautiful ragu bianco (a white meat sauce). ⁠From my cozy table in the back, I watched locals linger over dinner and bottles of local wine, and I popped outside every few minutes to watch the sunset from Piazza di San Francesco.

If you have favorite spots for wine tasting in Montepulciano, please share them!