Things to Do in Montepulciano: The Complete Insider Guide

Montepulciano is one of Tuscany's most rewarding destinations — and one of its most misunderstood. Most visitors come for the wine, tick the main square and leave. Those who stay longer discover something richer: a genuine medieval town with extraordinary food, art, architecture and experiences that go far beyond the obvious.

Here is the complete insider guide.

The Historic Centre

Start at the bottom — the natural entrance to Montepulciano is the Prato, where the road from Chianciano Terme meets the town walls. From here, climb the main corso through Via di Gracciano, Via di Voltaia and Via dell'Opio all the way to Piazza Grande. The walk takes about 20 minutes and passes through some of the finest Renaissance streetscaping in Tuscany.

Piazza Grande is the destination: a perfectly proportioned Renaissance square surrounded by the Palazzo Comunale, the Duomo, the Palazzo Nobili-Tarugi and the Palazzo Contucci. The proportions, the materials, the skyline — it is one of the most beautiful public spaces in Italy.

The Unmissable Sights

San Biagio (Church of the Madonna of San Biagio) — outside the town walls, about 20 minutes on foot from the Prato. A Renaissance masterpiece in golden travertine, designed by Antonio da Sangallo the Elder from 1518. At sunset, the building glows in a way that's almost supernatural.

The Torre del Palazzo Comunale — climb the tower for 360-degree views over the Valdichiana, the Val d'Orcia and, on clear days, Monte Amiata. The best viewpoint in town.

The Museo Civico — housed in Palazzo Neri-Orselli, containing Sienese paintings from the 13th–18th centuries. Quiet, rarely crowded, genuinely beautiful.

The Food

Montepulciano's cuisine is deeply Tuscan: simple ingredients, extraordinary quality, no concessions to fashion.

Pici all'aglione (thick handmade spaghetti with a Valdichiana garlic sauce) — at every serious trattoria. Bistecca di Chianina — the local breed of beef, some of the finest meat in Italy. Pecorino di Pienza — the famous sheep's milk cheese from 14km away, in every stage of ripeness.

The Wine Experiences

Wine is the obvious reason to come to Montepulciano — and the opportunities are excellent if you choose carefully.

For cellar visits: Avignonesi, Poliziano, Boscarelli, Salcheto.

For a genuinely exclusive private experience with a panoramic setting, maximum group size and a dedicated sommelier: Eramo Secret Garden. Our Sunset Wine Tasting, Tiramisù & Vino Nobile class, and Chef's Secret Table are all available by reservation.

Day Trips

Pienza — 14km, 20 minutes. The "ideal city" of the Renaissance, UNESCO-listed, famous for its pecorino and its extraordinary piazza.

Montalcino — 40km, 45 minutes. The home of Brunello — powerful, tannic, age-worthy reds from Italy's finest Sangiovese.

Chianciano Terme — 10km, 10 minutes. Thermal baths — an excellent way to spend a morning before an afternoon and evening in Montepulciano.

Practical Information

• Best time to visit: April–June and September–October
• How to get there: from the A1 motorway (Chiusi–Chianciano exit), 30 minutes by car. Nearest train: Chiusi (30km), with bus connection
• Parking: outside the town walls — the historic centre is pedestrian-only
• Language: English is widely spoken in wine and food establishments