From wine cellars in ancient tufa rock to the thermal cascades of Saturnia — a locals' guide to getting the most from your time in southern Tuscany.
The Real Montepulciano: A Local's Guide
Most visitors to Montepulciano arrive for the wine and leave two hours later. That's a shame, because the town and its surrounding countryside reward those who stay — deeply.
Here's how to fill a week without repeating yourself.
In the Town
1. Walk the Corso del Corso from bottom to top
The main street climbs steeply from Porta al Prato to the Piazza Grande at the summit. It's lined with medieval palazzi, Renaissance churches and enoteca after enoteca. Allow two hours and stop freely.
2. Piazza Grande at sunset
The main square at the top of town, framed by the Palazzo Comunale, the Duomo and the Palazzo Nobile-Tarugi, is one of the finest civic spaces in all of Italy. At sunset, with Vino Nobile in hand, it's unmissable.
3. Climb the Torre del Comune
The bell tower offers the finest views of the Val di Chiana and Val d'Orcia. Open most mornings for a small fee. The climb is steep but short.
4. Cellar bar-hopping
Many historic cellars beneath the town are open for tastings without appointments. Cantina de' Ricci, the Contucci cellars and Redi are all central and atmospheric. Bring your walking shoes — the stairs can be treacherous after three tastings.
5. Bravio delle Botti (last Sunday of August)
The town's annual barrel race — teams of two push enormous wine barrels up the steep Corso in a neighbourhood competition that's been running since the 14th century. If your trip overlaps, don't miss it.
The Surrounding Countryside
6. Pienza (20 min)
The "ideal city" of the Renaissance, built by Pope Pius II in the 15th century. Walk the main street in ten minutes, but linger in the side streets and the extraordinary cathedral that appears to hang over the Val d'Orcia. Don't leave without Pecorino di Pienza — the local sheep's milk cheese is exceptional.
7. Val d'Orcia scenic drive
The Cypress-lined roads between Pienza and San Quirico d'Orcia are among the most photographed landscapes on earth. Allow an afternoon, drive slowly, and stop wherever the light looks good.
8. Montalcino and Brunello (40 min)
Montepulciano's great rival for Tuscan wine supremacy. Brunello di Montalcino is arguably Italy's greatest red wine. The fortress at the top of town pours Brunello by the glass. Worth a half-day.
9. Cortona (40 min)
Made famous by Frances Mayes' Under the Tuscan Sun, Cortona is a beautifully preserved hilltop town with an excellent Etruscan museum and the finest views of Lake Trasimeno. Less visited than it deserves to be.
10. San Quirico d'Orcia and Bagno Vignoni (30 min)
Bagno Vignoni is unique: a medieval village whose central piazza is a large thermal pool rather than a square. No swimming (the waters drain to public baths below) but extraordinary to see. Combine with a coffee in San Quirico.
Food & Wine Experiences
11. Private Vino Nobile tasting at a producer
Any of the estates listed in our wine guide can be arranged with a private tasting — but as guests at Molino Nobile, we can set up access to producers who don't normally open to the public.
12. Cooking class with a local nonna
Several families in the Montepulciano area offer informal cooking lessons — pici (the thick hand-rolled pasta of the region), wild boar ragù, bruschetta with local olive oil. Ask us for our recommendation.
13. Truffle hunting at dawn
October to December is truffle season, but year-round experiences are available with a trained lagotto romagnolo dog. One of the most magical mornings in Tuscany.
14. Thermal baths at Saturnia or San Filippo
See our full thermal baths guide for details, but a morning at the Saturnia cascades is one of the great free pleasures of southern Tuscany.
15. Helicopter over the Val d'Orcia
For a special occasion, a 30-minute helicopter flight over the Val d'Orcia, Montepulciano and the surrounding countryside reveals a perspective that no road trip can replicate. Ask us for our recommended operator.
Getting Around
Montepulciano is not well served by public transport. A hire car is essential if you want to explore the surrounding countryside. We recommend:
- Car hire from Chiusi or Florence (both have train stations on the main Rome–Florence line)
- Private transfers from Florence airport (2hr) or Rome Fiumicino (2–2.5hr)
- Taxi from Chiusi-Chianciano station — about 20 minutes, around €30
As guests at Molino Nobile, we arrange all transfers on request.
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