Whenever you think of Italy, besides the wonders of Rome, Venice, or Florence your mind goes to the little villages in Tuscany. From north to south, Tuscany is plenty of small jewels to discover like Montepulciano, Italy.

In order to help you plan your stay, we have selected the 4 best villages in Tuscany you cannot miss during your visit.

Montepulciano, Italy

Montepulciano, one of the jewels of the Italian Renaissance, is appropriately known as the “Pearl of the 16th century”. Montepulciano (Italy) is romantic and rural at the same time, surrounded by idyllic cultivated hills.

You will be drawn back in time visiting this majestic medieval village with its historic architecture and ancient piazzas brimming with activity. When you arrive in the old town you will not notice its well-known ‘S’ shape (clearly visible from above), but you’ll soon notice the medieval walls that surround it.

The town meanders along the crest, with the Corso main street ambling upward, punctuated by the Piazza Grande, the city’s primary gathering spot and its civic and religious centre.

Located in the heart of wine-country, Montepulciano is also well known for the “Vino Nobile” Montepulciano wines. Montepulciano wineries are one of the destinations that we suggest you include in your travel schedule.

Our tip: Rent a Vespa or bicycle for the whole day and go on a picnic in the olive groves, experience a Pecorino di Pienza cheese tasting, or take an Italian cooking class.

Don’t miss:

Bravio of the Barrels, each year on the last Sunday of August, Montepulciano hosts a race of medieval origins consisting of a run … pushing wine barrels uphill.

The challenge takes place amongst eight districts which, in various corners of the old town, try to roll 80kg barrels on steep slopes uphill! Similarly to the medieval tradition a painted cloth is awarded to the winner.

Why choose Montepulciano, Italy:

Located between the Val d’Orcia and the Valdichiana, it is close to famous towns like Pienza, Montalcino, and Cetona. The hot springs of Chianciano Terme are close-by, and Lake Trasimeno is only about a half-hour away. Siena, Arezzo and Città della Pieve are all in reach, cities of artistic value worth seeing.

Pienza

Just 15 km west of Montepulciano lies the so-called “ideal city of the Renaissance”, Pienza. Part of the UNESCO’s heritage, this enchanting Renaissance village is surrounded by the Val d’Orcia, one of Tuscany’s most celebrated landscapes.

Pienza is a small jewel set among the Tuscan hills, its splendid square, its Renaissance palaces, rich in history and art, the alleys and the romantic panoramic views that overlook the Val d’Orcia make it unique..

Of course, the area is also known for producing some of Italy’s most famous wines. Nobile di Montepulciano and Brunello di Montalcino are world-renowned. Schedule a winery visit to sample these vintages. Pienza is also known for its distinct and delectable pecorino cheese. Try its various forms!

Our tip: Be sure to drive some of the country roads: the classic landscapes of the Val d’Orcia are the perfect postcard pictures! There are plenty of trails for walking and biking, as well.

How to reach Montepulciano, Italy

By train
Train station of Chiusi – Chianciano Terme: main line Rome – Florence – Bologna – Milan.
Continue with the regional train to Siena and get off at the Montepulciano station: Empoli – Siena – Chiusi line

By bus
LFI Bus (La Ferroviaria Italiana): urban and extra-urban services for Montepulciano. To consult the timetable visit the company’s website

By plane
Florence Airport (120 km)
Pisa Airport (160 km)
Rome-Fiumicino Airport (200 km)