Both of these medieval Tuscan towns are perched on a hill. Both are most known for their red wines. Both are ridiculously tiny and ridiculously crowded in August. Strolling the streets there is most certainly a Duomo to visit, another church or two, maybe a famous civic building or even a small museum, but the real draw is in the town itself. These aren’t destinations to visit to see a famous monument or tick off a site. You visit for the ancient stone streets, the Etruscan history, the paradisiacal views.

Montalcino and Montepulciano are separated by roughly 35 minutes of winding country road in Tuscany’s gorgeous Val d’Orcia. If you visit one, there’s no reason not to visit the other. A half-day visit is more than enough for each town. (You could even add Pienza located right between the two towns.) It’s two for the price of one! 



The entire town of Montalcino is just 94 square miles. To get there you’ll pass miles and miles of vineyards, winding your way to the top of this tiny mount where the town is perched. These are the vineyards of the excellent, if not expensive, Brunello di Montalcino, the town’s worldwide claim to fame.


Once upon a time, Montalcino was famous as a stopping point from Siena to Rome and an important fortress during the wars between Siena and Florence. Montalcino fought to hold out against Florence even after Siena fell, but was eventually economically suppressed in retaliation.


Once you finally make your way into the center (most parking is located outside the walls) you’ll immediately notice the imposing walls of the medieval fortress, and the views – Oh the views! Pay to climb to the top of the fortress to drink in even more views of Tuscany.



There’s more to drink than just the views. Montalcino is proud of its wine heritage, and the town is filled with dozens of enoteche (wine shops, often with tastings) to explore. After strolling the town and enjoying lunch al fresco, we headed out of town to the infamous Castello di Banfi vineyard to give the wines a try. The massive castle is actually a full fledged operation and a famous brand worldwide. We enjoyed a generous tasting of Brunello, Rosso di Montalcino, a younger, lighter, less expensive sister. Tourists milled about, eyeing the massive bottles and their massive price tags, the cyprus trees reached ever higher and we enjoyed our wine with views of the grapes growing right outside the window.

See more photos from Montalcino at A Tuscan Road Trip in Val d’Orcia



Like Montalcino, Montepulciano is characteristic, beautiful, filled with jaw-dropping views and excellent wine.

Still, the town holds its own. It was given an architectural facelift in the Renaissance after allying with Florence.

And I’d have to agree with Lee Marshall in the Telegraph who posits that Montepulciano hasn’t yet fallen into the tourist sinkhole that Tuscany’s San Gimignano or Cortona have. He says that the town is “below the radar enough and big enough (with a population of almost 15,000) to absorb its visitors gracefully, without becoming a tourist souk.”


A wine town since at least the 8th century, Vino Nobile reigns here. It was the first wine in Italy to gain a DOCG seal and one that has been called a wine of kings, of signori, throughout history. Be careful about drinking a vino nobile in the town’s cantinas though, if it’s too young it’s not holding up to its name. For a younger, less expensive wine, try the Rosso di Montalcino, made from the same grape but aged for less than half the time.

Montepulciano is also an excellent base for exploring the Val d’Orcia and north up to Florence. Siena, Florence, Cortona, Pienza, Montalcino, San Quirico d’Orcia, Bagno Vignoni, Monticchiello, and even Orvieto and Lake Trasimeno in Umbria are all an easy drive away.


Written by ginamussio

Leave a Reply

Your email address will not be published. Required fields are marked *