One of the highlights of our Etruscan Trails in Central Italy tour in May is our hotel stay immersed in the Tuscan landscape that surrounds Montepulciano. But the town’s midway location right in the heart of Italy makes it an ideal top or tail to any central Italy tour, an opportunity to explore more glorious architecture, wonderful vistas and to learn about some of the country’s finest wines.

Why visit Montepulciano?

One of Tuscany’s larger medieval hilltop towns, Montepulciano’s architecture displays multiple echoes of Florence, but while equally refined, the town’s overall atmosphere is less frenetic. The town dates back to the 4th century BC, although the existing walled town was built around the 14th century AD.

The surrounding countryside is another good reason for visiting. Set on a chalky hilltop on a ridge that divides the Val D’Orcia from the Val di Chiana, the town is surrounded by hills, fields, and fertile vineyards. Not surprisingly, food and wine are a highlight, with the town best known for its Vino Nobile red wine.  Our tour here runs in May when the landscape is a glorious, vibrant green.

Top things to see in Montepulciano

Wander leisurely through the streets to really absorb the atmosphere. Enter the long, narrow town via Porta al Prato at the north end, and climb uphill along the town’s main road, Il Corso. The street’s name changes as you proceed past the late Renaissance Palazzo Avignonesi and Palazzo Cocconi, ultimately leading to Piazza Grande, the centre of town. Take time too to veer off down side streets, past boutique shop windows and wine cellars, to enjoy the view.

Torre di Pulcinella

One of the first sights is the Torre di Pulcinella, opposite the church of Sant’Agostino. The medieval tower is topped by the town clock and the unlikely statue of Pulcinella (or Punch of ’Punch and Judy’ fame), a traditional ‘commedia dell’arte’ figure which was apparently brought to the town by a bishop of Neapolitan origins.

Piazza Grande

The main Piazza Grande is home to some of the town’s most important buildings and grand façades, including the Palazzo Comunale, the Duomo, the Palazzo del Capitano del Popolo and the historic Palazzo Contucci. Set at the highest point of town, this is also the place to catch up on cultural events, summer festivals and open-air concerts under starry skies. The square has also been used as a film set on several occasions, including in Under the Tuscan Sun, and in the Twilight vampire series, where Montepulciano stood in for Volterra.

The Palazzo Comunale (the Town Hall) is set on the south side of the square. Originally constructed in the 14th century, and remodelled in the 15th century by Michelozzo, the building’s Gothic-style façade and tower is reminiscent of the Palazzo Vecchio in Florence. Climb to the top of the clock tower (or take the lift) for the best views as far as Pienza and Montalcino.

The 16th century Duomo, or Cathedral of Santa Maria Assunta, sits opposite the Palazzo Comunale. Its façade is surprisingly simple, contrasting with a more elaborate interior that includes a huge altarpiece, the huge Assumption triptych (1401) by Taddeo di Bartolo.

Other historic buildings on the Piazza Grande include the Palazzo del Capitano del Popolo and the Contucci Palace, built by the Florentine architect Antonio di Sangallo the Elder. The palazzo has been home since the 11th century to the aristocratic Contucci family who today offer wine tastings and cellar tours.

Sangallo was also responsible for the Palazzo Nobili-Tarugi and the adjacent Pozzo dei Grifi e dei Leoni, a well bearing a gryphon and the Marzocco, representing Montepulciano and Florence respectively.

Chiesa di San Biagio

The Basilica of San Biagio is generally regarded as the town’s tour de force. Set just outside the historic centre, against a backdrop of vineyards and oak forests, the white travertine church, with its Greek cross plan and central dome, is slightly atypical of other Tuscan churches. This too is the work of Antonio da Sangallo and is said to have inspired Michelangelo’s first plans of what became St Peter’s Basilica in Rome.

Places to visit near Montepulciano

Montepulciano is a great base for exploring much of Tuscany and neighbouring Umbria. Siena, Cortona, Perugia and Arezzo are all within an hour’s drive while Volterra, San Gimignano and Florence are a little further.

Don’t miss tiny Pienza, renowned for its pecorino cheese, and Montalcino, home to Brunello di Montalcino wine. We recommend Sarteano and Chiusi for anyone interested in Etruscan history, and, to the south of Montepulciano, Chianciano Terme is known for its thermal waters.  There are also natural hot springs at nearby Bagno Vignoni which are definitely worth a visit after a day of sight seeing.

You’ll also find plenty of pleasant hiking routes, including an 8km half day walk along a cypress-lined avenue and country lanes to the walled hamlet of Montichiello.

What to eat and drink in Montepulciano

This is the heart of the world-famous area responsible for producing Nobile di Montepulciano and Brunello di Montalcino wines. Its Vino Nobile is one of Tuscany’s most esteemed wines, made from grapes grown in surrounding vineyards, with a minimum of 70% Sangiovese grapes. The wine is aged for at least 2 years, one of which must be in an oak barrel.

Unsurprisingly, the food is every bit as good as the wine. Feast on Cinta Senese prosciutto, platters of cold meat and cheese, pappardelle pasta with wild boar sauce, ‘pici’, a thick, hand-rolled spaghetti with a spicy tomato sauce, and hearty meat dishes, including bistecca alla Fiorentina from Chianina cattle.

Cultural events in Montepulciano

Montepulciano’s best-known event is the Bravìo delle Botti which, each August, sees the 8 districts of Montepulciano compete in a race to push a heavy wooden wine barrel uphill through the medieval centre to the finish line in front of the Duomo in Piazza Grande. Other events include Carnevale and an annual Easter festival, when classical music concerts are held in palazzos, churches and other sites in the town over a 2-week period. For wine-lovers, Montepulciano’s participation in the Cantine Aperte initiative is an opportunity to visit some of the superb wine cellars.

Transport and travel connections in Montepulciano

Montepulciano is easily accessible by road, rail, or air. The nearest airport is around 70km away in Perugia, Florence Peretola airport around 120km away, and Rome around 190km.

To reach Montepulciano by train, there are two options. Montepulciano station is about 15km outside town, requiring an onward 20-minute journey by bus (limited service), or a taxi transfer. Alternatively, Chiusi-Chianciano station in Chiusi is around 30 minutes from Montepulciano.

Travelling by car is probably the easier option. Choose from one of several car parks around town, including one near the fortress or just outside Porta al Prato.