The Ideal 2-Day Itinerary for Montepulciano

Two days in Montepulciano, planned well, offer one of the most complete Tuscan experiences available in any short trip. Art, wine, food, landscape and genuine cultural immersion — all within a single medieval hilltop town and its immediate surroundings.

Here is the hour-by-hour plan.

Day 1 — Arrival and the Town

Morning (9:00–12:30)

Arrive at Montepulciano from Florence (1h30) or Rome (2h30). Park at the Prato (lower entrance, free parking).

Walk the entire corso from bottom to top — Via di Gracciano, Via di Voltaia, Via dell'Opio to Piazza Grande. Stop at an alimentari on the way for a coffee and a piece of schiacciata (Tuscan flatbread, olive oil, rosemary).

At Piazza Grande: visit the Duomo (free, extraordinary Taddeo di Bartolo triptych inside) and climb the tower of the Palazzo Comunale (small fee, 360° view).

Midday (12:30–15:30)

Take the footpath down to San Biagio (20 minutes through the vineyards — NOT the road). This is one of the most beautiful walks in Tuscany and almost nobody does it.

Spend 30 minutes at San Biagio — the golden travertine church, alone in its vineyards, is one of Antonio da Sangallo the Elder's masterpieces. The silence here, compared to the crowds above, is part of the experience.

Drive to Pienza (14km, 20 minutes). Buy lunch from the producers on Via Rossellino — pecorino in every stage of ripeness, local salumi, Tuscan bread. Eat it at the Giardini Pubblici with a view of the Val d'Orcia.

Afternoon (15:30–17:30)

Return to Montepulciano. Visit one cantina — Salcheto is the best for visitors (sustainable winery, excellent guide, great wines). Book the day before via their website.

Evening — The Highlight (18:00–21:30)

Eramo Sunset Wine Tasting: 2.5 hours, five Vino Nobile wines, chef-prepared pairings, AIS sommelier, panoramic private garden. This is the defining experience of the first evening.

Dinner: light, after the tasting. Ristorante Diva e Maceo for pici al ragù and a glass of Rosso di Montepulciano.

Day 2 — The Val d'Orcia and the Final Experience

Morning (9:00–12:00)

Start early. Drive the Val d'Orcia circuit: south from Montepulciano on the SP146 towards San Quirico d'Orcia. Stop at every viewpoint. This is the landscape on a thousand postcards — you're driving through it.

At San Quirico d'Orcia: visit the Collegiata and the Horti Leonini (the Renaissance garden behind the main square). Almost no tourists.

Continue to Bagno Vignoni — the extraordinary medieval thermal piazza (a square filled with hot thermal water instead of a fountain). Have a coffee at one of the surrounding cafés.

Return via Pienza if you want more pecorino. Otherwise, return directly to Montepulciano.

Midday (12:30–14:30)

Pasta Fresca & Vino class at Eramo — if booked. Three hours of hands-on pasta making followed by lunch with what you made, paired with Vino Nobile. This is the second major experience of the trip.

Alternatively: lunch at Caffè Poliziano (the 1868 literary café) for the terrace view.

Afternoon (14:30–17:00)

The Museo Civico (Palazzo Neri-Orselli) for those interested in Sienese painting. Otherwise: walk the less-visited parts of town — the area around Via del Teatro and the northern bastions.

At 17:00: buy the wines to take home. The Enoteca Consortile on Via di Gracciano is the best place — knowledgeable staff, honest prices, the full range of the denomination.

Evening (17:30–)

Watch the sunset from the western walls. Then dinner — and a final glass of Vino Nobile Riserva before departure.

Two days done properly in Montepulciano. You'll be back.