One Day in Montepulciano: The Perfect Itinerary

One day in Montepulciano is never enough. But if that's what you have, here's exactly how to spend it — tested, hour by hour, by people who know the town well.

Morning: Arrival and the Historic Centre (9:00–12:30)

9:00 — Arrive at the Prato (the lower entrance to Montepulciano). Park outside the town walls — the historic centre is pedestrian-only and the walk up is part of the experience.

9:15 — Begin climbing the main corso. Stop at the alimentari on Via di Gracciano for a coffee and a schiacciata (Tuscan flatbread) from the local bakery.

10:00 — Arrive at Piazza Grande. Visit the Duomo (free entry), climb the tower of the Palazzo Comunale for the panoramic view (small entry fee, worth every cent), and walk the perimeter of the square.

11:00 — Visit the Museo Civico if you're interested in Sienese painting. Otherwise, explore the side streets — the area around Via del Teatro is particularly beautiful and rarely visited.

11:45 — Begin the descent to San Biagio on foot (20 minutes down the hill through the vineyards). This is one of the finest walks in Tuscany.

12:15 — Arrive at San Biagio. The Renaissance church in golden travertine is one of Antonio da Sangallo the Elder's masterpieces. Spend 20 minutes here in relative silence.

Midday: Pienza (13:00–15:30)

13:00 — Drive to Pienza (14km, 20 minutes). This is not optional — the "ideal city" of the Renaissance, with its extraordinary piazza and the best pecorino in Tuscany, is essential viewing.

13:30 — Lunch in Pienza. Buy bread, pecorino, local salumi and a bottle of Rosso di Montepulciano from the shops on Via Rossellino and eat in the Giardini Pubblici with a view of the Val d'Orcia.

14:30 — Visit Piazza Pio II. The proportions are extraordinary. Walk through the Palazzo Piccolomini if open (exceptional views from the loggia).

15:15 — Return to Montepulciano.

Afternoon: Wine and Rest (15:30–17:30)

15:30 — Rest at your accommodation or explore the wine shops on Via Voltaia. This is the time for a single cantina visit — choose Poliziano or Salcheto and book in advance.

17:00 — Freshen up. The main event of the day is about to begin.

Evening: Sunset at Eramo (18:00–21:00)

18:00 — Arrive at Eramo Secret Garden for the Sunset Wine Tasting. The garden opens as the light begins to shift towards golden hour.

The next 2.5 hours: five Vino Nobile wines, chef-prepared food pairings, a dedicated sommelier and a view that explains why people have been writing poetry about this landscape for 700 years.

20:30 — Dinner in Montepulciano. The Osteria del Conte or Ristorante Diva e Maceo for local cuisine at its best.

One day, done perfectly. Montepulciano will want you to come back.