What to see in Montepulciano in 2 days: itinerary through Renaissance palaces and vineyards
Guide on what to see in Montepulciano in 2 days: Piazza Grande, Nobile wine cellars, San Biagio Temple, Val di Chiana views and trips to Pienza.
Why visit Montepulciano in 2 days
Montepulciano is the quintessence of Tuscany: a Renaissance hilltop town perched at 605 metres, surrounded by vineyards that produce the celebrated Vino Nobile. Steep streets flanked by sixteenth-century palaces, underground cellars carved into tufa and sweeping views over the Val di Chiana and Val d'Orcia make this place irresistible. Two days are perfect to explore the town, visit the wineries and discover the surroundings.
Day 1: the old town
Morning: climbing to Piazza Grande
Start from Porta al Prato, the main gateway, and begin the ascent along the Corso, the street that crosses Montepulciano from south to north. The uphill route is lined with Renaissance palaces designed by great sixteenth-century architects: Palazzo Avignonesi, Palazzo Bucelli with its facade decorated with Etruscan urns, and the Palazzo del Capitano del Popolo.
Reach Piazza Grande, the monumental heart of the town. The Cathedral holds Taddeo di Bartolo's Assumption triptych. Opposite, the Palazzo Comunale, designed by Michelozzo on the model of Florence's Palazzo Vecchio, offers from its tower a view that on clear days reaches as far as Monte Amiata and Lake Trasimeno.
Afternoon: cellars and Vino Nobile
Montepulciano is a town built above a labyrinth of cellars. In the afternoon, descend into the caves carved into Etruscan tufa where Vino Nobile DOCG ages. The Cantine De' Ricci beneath Palazzo Ricci and the Cantina Contucci in Piazza Grande offer tastings in atmospheric underground settings. Vino Nobile is an elegant Sangiovese with hints of cherry and spice.
Then stroll through the side streets, discovering shops selling local products: Pienza pecorino, honey, artisan pasta and the prized local saffron.
Evening: sunset from the Fortress
Head to the Medici Fortress for sunset. The walls offer a privileged vantage point to watch the sun descend over the Val di Chiana, painting the cypresses and vineyards orange.
Day 2: San Biagio and surroundings
Morning: the Temple of San Biagio
Descend from the town towards the Temple of San Biagio, a masterpiece by Antonio da Sangallo the Elder. This centrally planned Renaissance church, set amid greenery at the foot of the hill, is one of the most harmonious buildings of the Italian Renaissance. The luminous travertine interior and the perfect acoustics are breathtaking.
Climb back via the panoramic road that offers views of the temple framed by cypresses: one of Tuscany's most photographed images.
Afternoon: Val d'Orcia
Devote the afternoon to the UNESCO-listed Val d'Orcia. Pienza, just 13 km away, is the ideal Renaissance city commissioned by Pope Pius II: the trapezoidal piazza, the Cathedral and the pecorino shops deserve at least a couple of hours. Alternatively, the thermal baths of Bagno Vignoni with their hot-spring piazza offer a surreal and relaxing experience.
On the way back, stop along the cypress-lined road of San Quirico d'Orcia for the quintessential Tuscan landscape photograph.
Evening: dinner with a view
End with a panoramic dinner in Montepulciano, accompanied by a glass of Nobile and the night-time view over the illuminated valley.
Viewpoints not to miss
- Palazzo Comunale tower: 360-degree view over Val di Chiana and Val d'Orcia
- Medici Fortress: sunset over vineyards and countryside
- Panoramic road to San Biagio: views of the temple and cypresses
- Via di Voltaia nel Corso: southward outlook over the Val d'Orcia
Secret corners
- The dead-end alley behind the Cathedral, with a hidden valley overlook
- The steps descending from Via del Teatro towards the medieval cellars
- The hanging garden of Palazzo Contucci, unsigned
- The fountain at Porta al Prato, an ancient washhouse beneath the walls
Practical tips
Montepulciano is entirely uphill and the streets are stone-paved: comfortable shoes are essential. Summers are hot but the altitude ensures cool evenings. The town is served by external car parks with an escalator. Wineries often require booking for tastings. The last weekend of August sees the Bravio delle Botti, a barrel race between the town's districts.
