Montepulciano is a medieval town on a hilltop in Tuscany, Italy. The town is hidden away, surrounded by robust vineyards. It is known for its Vino Nobile Tuscany’s most serious, full-bodied red wine. Coming here is like traveling back in time, apart from sporadic restorations, no major building has taken place since 1580. The population of locals is almost 15,000, and even at the height of summer, you never feel like you are stuck in a tourist trap.
Driving through Tuscany has been one of my favorite experiences around Europe because of the medieval towns and history. The rare landscape gives a phenomenal drawl to the place. I like to spend a few days vineyard hopping and wine tasting, then a few days seeing the ancient town of Montepulciano – enjoying the Tuscan cuisine, and walking it off after. I end my Tuscan travels at the hotel Lupaia where I sit by the pool – taking in the picturesque scenery lined with Tuscan Cypress trees.
By now I have purchased quite a few bottles of ridiculously good Tuscan wine. When it rains, it is a blessing. I sit on the porch under the vines with a book, blanket, and glass of wine. This is one of the only places I can fully relax while anticipating the sunset. There is nothing quite like the sunsets in Tuscany. The dust from the vineyards rises into the atmosphere – allowing for some deep orange hues.
Here is a list of restaurants to check out:
Piccola Trattoria Gustini
Ristorante Villa Nottola
Here are two amazing options for booking wine tours. You can also follow their itineraries and do it yourself if you prefer. But never a good idea to drink and drive.
Tuscan Wine Tasting Tours
Montepulciano history dates back to the 4th century B.C. According to legend, it was founded by Porsenna, king of the Etruscan city of Chiusi. After the Etruscan rule, the Romans came who used the area as a military camp.
From the 12th century, this town became more prominent and entered the sphere of influence of the Siena Republic. During the 13th century, the strategic location and its many commercial and manufacturing activities made Montepulciano a very popular and disputed destination between the historical enemies of Florence and Siena. The next century is marked by constant struggles for power over these lands: at the end of this tumultuous period, the city chose to ally itself with Florence. The 15th century was the beginning of a thriving time, made up of political and social balance that favored a cultural renaissance that lasted until the mid-16th century.
Montepulciano, at that time, was the center of the commercial and artistic life of the Val di Chiana: in 1467, with the establishment of Monte Pio, one of the first banks in the world was founded here. Even then the Montepulciano red wine was known and sold abroad.
Vino Nobile di Montepulciano DOCG is grown in the areas of the province of Siena and is one of the oldest Italian wines. Some documents of merchants of the 14th century provide the first evidence of its value as an export product of top quality. Another clue to its fame can be found in the work ‘Bacchus in Tuscany’ (1685), in which the naturalist and physician Francesco Redi says ‘Montepulciano of every wine is King!’
The endorsement ‘Nobile di Montepulciano’ dates back to the 18th century, but the establishment of this as its official name came in the 20th century thanks to Adamo Fanetti, the first producer of this wine which is today still labeled as ‘Noble’.
Each year on the last Sunday of August, Montepulciano hosts a race of medieval origins consisting of a running while pushing wine barrels uphill. Similarly to the medieval tradition, a painted cloth is awarded to the winner.
The castle of Montepulciano
Piazza Grande, situated at the highest point of the town, is the center of Montepulciano and is dominated by the great tower and the Gothic façade of the Palazzo Comunale. From the top of the tower, you can see as far as Radicofani, the Val d’Orcia and the Lake Trasimeno. The square is lined with some grand buildings like the Cathedral and the Town Hall. There are also restaurants and cafes.
Montepulciano’s cathedral is situated on the southern side of Piazza Grande. Its façade is unfinished but inside there is a very impressive altarpiece created in 1401, painted on wood and decorated with gold.
The Palazzo Comunale (Town Hall) is situated in Piazza Grande and you can climb to the top of the tower to enjoy a fantastic view.
The church of Santa Maria delle Grazie (late 16th century) has a simple Mannerist façade with a three-arcade portico. The interior has a single nave and houses a precious terracotta altar by Andrea della Robbia.
Montepulciano is car-free. Cars are not allowed inside the historical old center unless you have a permit, so you must park at the edge of the town. Note that in summer it will be crowded. Wear your walking shoes, you will be walking uphill a lot.
There is no train station in Montepulciano so I recommend you either rent your own car or book a tour that includes a visit to the town.