Montepulciano: all the places to visit in this renowned Tuscan village

Montepulciano rises among the gentle hills of the Val di Chiana and is regarded as one of Tuscany’s most enchanting villages. Wandering through its cobbled streets and Renaissance palaces offers not only architectural delights but also breathtaking views over the surrounding countryside.

Famed above all for its connection to the region’s wine production, this town also boasts a history stretching back thousands of years. It remains an unmissable stop for anyone exploring the Tuscan heartland, offering the chance to discover not only its celebrated wines but also the charm of a place steeped in history and tradition, with an identity that has endured through the centuries. Here is what to see in and around Montepulciano.

Where Montepulciano is located

Montepulciano lies in the province of Siena, in the southeastern corner of Tuscany, just a few kilometres from the border with Umbria. Perched on a ridge at an altitude of 600 metres, it offers sweeping views over the Val di Chiana and, further in the distance, the Val d’Orcia.

The town is easily accessible from Siena, Arezzo and Perugia, and is also well connected to nearby spa destinations such as Chianciano and Bagno Vignoni. It is an ideal spot for travellers seeking a blend of culture and relaxation.

A village with ancient roots

The history of Montepulciano stretches back to Etruscan times, as evidenced by artefacts unearthed in the surrounding countryside and underground structures that have been repurposed over the centuries. By the Middle Ages, the town had become an important strategic and commercial hub, fiercely contested by Florence and Siena due to its commanding position. 

During the 15th and 16th centuries, Montepulciano experienced a remarkable period of artistic and architectural flourishing, driven by the patronage of noble families who welcomed renowned architects and artists. This rich historical layering remains visible today in its palaces, churches and narrow alleys.

Why Montepulciano is famous

The first thing that comes to mind when Montepulciano is mentioned is undoubtedly its wine, which is the main reason for the town’s renown. This is the celebrated Vino Nobile di Montepulciano, one of Tuscany’s most prestigious labels and among the first to receive the DOCG designation. This full-bodied red was already renowned during the Renaissance and continues to attract producers, connoisseurs, and travellers from around the globe.

Beyond its wine, Montepulciano also captures the hearts of visitors with its remarkable artistic heritage. The town boasts stunning squares, medieval alleyways, cobbled streets, and Renaissance churches. Several film scenes have also been shot here, adding to its timeless charm.

What to see in Montepulciano

Piazza Grande

Undoubtedly the beating heart of the town, Piazza Grande is framed by some of Montepulciano’s most iconic buildings: the Palazzo Comunale, modelled on Florence’s Palazzo Vecchio; the Cathedral of Santa Maria Assunta; and the Renaissance palaces of Tarugi and Contucci. In the summer months, the square comes alive with cultural events and historical re-enactments, including the famous Bravìo delle Botti. 

Wandering down any of the narrow streets leading away from the square reveals a wealth of hidden details: coats of arms, secluded courtyards, loggias and charming balconies.

The Cathedral

Dominating Piazza Grande with its imposing façade, Montepulciano Cathedral offers a serene interior where notable works of art, such as Taddeo di Bartolo’s triptych, can be admired. The understated yet solemn atmosphere provides a moment of quiet reflection, far removed from the bustle of modern life.

The Medici Fortress

Partially restored, the Medici Fortress now serves as a venue for cultural events and wine tastings, while also offering one of the most breathtaking panoramas of Montepulciano. From its walls, the rolling hills of Tuscany stretch out towards the horizon, with Lake Trasimeno visible in the distance. The fortress also houses one of the offices of the Consorzio del Vino Nobile, where visitors can take part in guided tastings of the area’s celebrated wines.

The Corso and the historic wine cellars

The main street of the town is the Corso, a gently ascending road that links Porta al Prato with Piazza Grande. Along its route, visitors encounter artisan workshops, historic cafés and underground cellars carved into the tuff, many of which are open to the public. Some of these cellars date back to Etruscan times and contain enormous barrels. Among the most renowned are the De’ Ricci and Contucci cellars, true stone labyrinths where wine matures in secrecy.

The temple of San Biagio

Just outside the city walls, at the foot of the hill, stands the splendid Renaissance church of San Biagio, regarded as one of the most beautiful in Tuscany. Designed by Antonio da Sangallo the Elder, the temple is a masterpiece of harmony. Surrounded by greenery, it occupies an especially picturesque position and offers an excellent vantage point to admire Montepulciano from below.

Museums and small treasures

Among the cultural highlights of the town, the Museo Civico Pinacoteca Crociani is not to be missed. The museum houses an impressive collection of paintings, sculptures and liturgical furnishings dating from the 13th to the 19th century. Also worth a visit is the Church of St Augustine, notable for its façade by Michelozzo and a crucifix attributed to Donatello.

Traditions and events

The most renowned event is without doubt the Bravìo delle Botti, a historic competition in which the town’s districts challenge each other by rolling barrels uphill through the streets. In summer, the International Art Workshop fills various venues in the centre with concerts and theatrical performances. In winter, the town transforms into a magical setting, hosting a charming Christmas market within the walls of the Fortress.

Montepulciano, a town to experience

Visiting Montepulciano means discovering its wine, its history and its architectural treasures. It also means stepping into a world of unhurried rhythms. The sandstone houses, the tranquillity of its narrow lanes and the sweeping views over the Tuscan countryside make it a serene and welcoming place. Here, one can take a pause to savour a glass of wine in a cosy enoteca or simply sit on a bench, watching the sun set over the rolling hills.

What to see around Montepulciano

Montepulciano is also an ideal base for exploring the landscapes and villages of the Val di Chiana and the Val d’Orcia. Just a few kilometres away lies Pienza, another Renaissance gem created under the patronage of Pope Pius II.

Further south, Chianciano Terme has been renowned since ancient times for its therapeutic waters. The small fortified village of Montefollonico is also well worth a visit.

Nature lovers will discover a true paradise in the rolling hills, dotted with vineyards, olive groves and cypress trees, and interlaced with numerous trails perfect for walking or cycling. For those seeking relaxation, the thermal baths at Bagno Vignoni and Bagni San Filippo offer the perfect retreat.

Article translated by Agnese Giardini