TThis itinerary links two of the most celebrated hill towns of southern Tuscany — Pienza and Montepulciano — through Renaissance architecture, historic wine cellars and the landscapes that have made the Val d’Orcia famous worldwide. You’ll follow a curated Google Maps route guiding the day step by step along scenic countryside roads. At the foot of Montepulciano, beside the Renaissance Temple of San Biagio, you’ll meet your licensed guide, who will accompany you through the historic centers of Montepulciano and Pienza, revealing the architecture, history and traditions that shape this remarkable corner of Tuscany.
Renaissance towns, underground cellars, countryside roads and the flavors of southern Tuscany — a day where architecture, landscape and food naturally come together
The day begins just outside Montepulciano at the Temple of San Biagio, one of the purest examples of Renaissance architecture in Tuscany. Designed by Antonio da Sangallo the Elder in the early 16th century, the church rises in perfect symmetry at the foot of the hill, surrounded by open countryside.
Seen from here, Montepulciano appears above the landscape as a compact stone crown. The stop offers a first introduction to the Renaissance vision that shaped this territory, where architecture, geometry and landscape were conceived as part of the same harmonious composition.
The route then continues into the historic center, reaching Piazza Grande, the monumental heart of Montepulciano. Here the Cathedral, the Palazzo Comunale and the surrounding Renaissance palaces create one of the most recognizable architectural ensembles in southern Tuscany — a setting so scenographic that it has served as the backdrop for several international films.
The walk continues toward the upper edge of Montepulciano, reaching the Medici Fortress. The original stronghold dates back to 1261, when the Republic of Siena fortified the hill during its long rivalry with Florence. The structure visible today reflects later Renaissance interventions associated with the Medici domination of the town and the military architecture developed in the 16th century.
Set at the highest point of Montepulciano, the fortress overlooks both the Val d’Orcia and the Val di Chiana, making it one of the most strategic viewpoints of the town. Today the complex hosts cultural spaces and the Enoliteca of the Consorzio del Vino Nobile di Montepulciano, representing the historic wine tradition of the area.
This part of the visit also becomes the natural setting for the first wine tasting of the day, introducing the territory and the long-standing culture of Vino Nobile before continuing the walk through the town.
The route then descends through Via di Voltaia, the lively street linking the upper and lower parts of the town. Small shops, artisan stores and wine boutiques line the path, offering a glimpse of the everyday rhythm of Montepulciano’s historic center and a bit of time to explore before the next stop.
The visit continues inside a second historic cellar carved beneath the town. Vast brick vaults, stone pillars and underground corridors reveal how Montepulciano extends below street level, where architecture and wine production have been intertwined for centuries.
Leaving Montepulciano, the route moves through the surrounding countryside between vineyards, rolling hills and farm estates. The landscape gradually opens toward the Val d’Orcia, transitioning from the stone urban fabric of the town to the agricultural scenery that defines this UNESCO-protected territory.
Arriving in Pienza, the rhythm of the day pauses for a light lunch in the historic center. The focus here is on the local specialties of the Val d’Orcia: Pecorino di Pienza in its different ages, traditional cured meats, and simple Tuscan accompaniments that reflect the agricultural culture of this landscape.
Served in a relaxed setting, the tasting offers a chance to experience the flavors that define this part of southern Tuscany — sheep’s milk cheeses, artisanal salumi and the rustic food traditions that have long accompanied life in these hills.
A moment to slow down, enjoy the atmosphere of Pienza, and taste one of the gastronomic symbols of the Val d’Orcia before continuing the visit through the town.
Guided visit of Pienza, the “ideal city” created in the 15th century for Pope Pius II. Perfectly proportioned squares, elegant palaces and harmonious streets make it one of the clearest expressions of Renaissance urban planning, framed by sweeping views over the Val d’Orcia landscape.
| Guests | Total price | Per person |
|---|---|---|
| 1–2 | €530 | €265 |
| 3 | €600 | €200 |
| 4 | €660 | €165 |
| 5–10 | + €60 per person | |
| 11+ | Available on request | |
