10 Hidden Gems in Montepulciano You Won't Find in Guidebooks

Montepulciano is one of Tuscany's most visited hilltop towns — and yet it hides an extraordinary number of things that most visitors never find. Here are 10 of the best.

1. The Eramo Secret Garden

The name says it. A private walled garden with 360-degree panoramic views over the Val d'Orcia, accessible only by reservation and hosting a maximum of 18 guests at a time for exclusive wine and food experiences. It does not appear on tourist maps. Our Sunset Wine Tasting is the way to discover it — at the moment when the light on the hills is most extraordinary.

2. The Underground Cantina Network

Montepulciano is built on tufa — a volcanic rock that creates natural cellar conditions. Beneath the streets, an extensive network of ancient cellars runs under the town, some dating back to Etruscan times. The Cantina della Fortezza (under the old fortress walls) is one of the most spectacular. Most tourists walk past the entrance.

3. The Saturday Market

Every Saturday morning, local producers set up outside the town walls. Here you'll find pecorino directly from the Pienza farms, local honey (including the extraordinary chestnut honey from the Monte Cetona forests), seasonal vegetables, wild herbs and salumi from the local pig breeds. Prices are a fraction of the tourist boutiques.

4. The Western Wall at Sunset

Walk the western ramparts of Montepulciano in the final 90 minutes before sunset — from the Porta al Prato to the Bastione di Sangallo. The views over the Val d'Orcia, with Pienza visible on its ridge 14km to the southwest, are among the finest in Tuscany and remarkably uncrowded.

5. Monticchiello and Its Teatro Povero

15km from Montepulciano, this tiny medieval village is entirely unknown to most tourists. Every summer, the whole community writes and performs a play (Teatro Povero) commenting on contemporary Italian social and political life. The village itself, with its intact 14th-century walls and a single perfect piazza, is extraordinary at any time of year.

6. The Palazzo Contucci Cellar

The Palazzo Contucci is one of the palaces facing Piazza Grande — and beneath it runs one of the oldest operating wine cellars in Montepulciano. The Contucci family has been producing Vino Nobile since the 18th century. Tastings are informal, personal and completely different from the commercial cantina experience.

7. The Dawn Light on Piazza Grande

Visit Piazza Grande before 8am. The square — which by 10am will be dotted with tour groups — is completely empty. The travertine of the Palazzo Comunale catches the early light differently than at any other time of day. It is one of the most beautiful spaces in Renaissance Italy, and in the early morning, it feels entirely private.

8. The Wine from the Producers' Cooperatives

Not every Vino Nobile is from a famous estate. The Cantina Cooperativa di Montefollonico produces wine from small growers throughout the denomination — wine that rarely appears in export markets but is excellent value. Ask for it at the local alimentari rather than the tourist enoteche.

9. The Pici at the Thursday Lunch Crowd

At the small trattorias that cater primarily to locals — find them on the streets parallel to Via Voltaia — the Thursday lunch menu invariably includes fresh pici al ragù. This is when the pasta is freshest (market day is Thursday), the customers are all regulars and the kitchen is cooking for people who live here. The experience is completely different from dinner for tourists.

10. The Vineyard Road to San Biagio

Most visitors take the road to San Biagio. The real experience is the footpath: a 20-minute walk downhill from the Prato, through the Prugnolo Gentile vineyards, with views back up to the town walls. In April-May, the vineyards are flowering and the air smells of blossoms. In September, the grapes hang heavy and ripe. It's free, it's beautiful and almost nobody does it.