Your calves will register the slope long before your eyes settle on the Piazza Grande. Built along a narrow limestone spine between the Val di Chiana and the Val d'Orcia, this high medieval town funnels you upward past sixteenth-century palazzi to vaulted cellars cut straight into the tufa. You come for the Vino Nobile di Montepulciano, aged in massive oak casks underground, and stay for plates of hand-rolled pici tossed in garlic and breadcrumbs.
Last updated 28 Aug 2026



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Montepulciano runs along a steep single ridge, demanding sturdy shoes and rewarding you with underground cellars and high Renaissance stone. Days revolve around cellar tours, unhurried lunches of thick pici pasta, and evening strolls along Via del Corso. It suits independent walkers, wine lovers, and travellers who prefer quiet evenings over late-night commotion.
Enter through Porta al Prato at nine and wind up Via di Gracciano. Tour the subterranean vaults of Cantina Ercolani or De' Ricci, pause for pici all'aglione on Via di Voltaia, then reach Piazza Grande before climbing the town hall tower by four for sunset. Select 1 Day above to see it.
A second day lets you walk out through Porta delle Farine down to San Biagio in the morning light. Spend the afternoon tasting Rosso di Montepulciano at small estates on the road toward Monticchiello, finishing with grilled Chianina steak in a rustic cellar. Choose 2 Days to expand the plan.
With three days, venture across the clay knolls of the Val d'Orcia to Pienza for aged pecorino, or soak in the hot mineral waters at Bagno Vignoni. You return each evening without hurry, taking an outdoor table for a quiet glass of Vin Santo as the valley cools.
Cellars like De' Ricci and Contucci age Vino Nobile from Sangiovese grapes inside vast vaulted caverns carved directly into the rock below the streets.
Antonio da Sangallo the Elder left his mark on the town hall facade and the freestanding Renaissance temple of San Biagio just below the city walls.
Pici are thick, hand-rolled Tuscan noodles, best served all'aglione with local sweet garlic or with a slow-simmered wild boar ragu at a wooden table.
The Duomo on Piazza Grande houses Taddeo di Bartolo's 1401 Assumption of the Virgin triptych, flanked by stone works from Michelozzo.
Climb the tower of Palazzo Comunale on clear mornings for panoramic views across the Val d'Orcia, Lake Trasimeno, and distant Monte Amiata.
A gravel path descends through olive groves from Porta al Prato down to the sixteenth-century travertine dome of the Madonna di San Biagio.
Butchers along Via di Gracciano nel Corso slice salty Cinta Senese prosciutto, wild boar salumi, and fennel-dusted finocchiona.
Workshops tucked into alleys along Via di Voltaia produce hand-stitched leather goods, hammered copper cookware, and hand-thrown ceramics.
The sulfur springs of Terme di Montepulciano and nearby Bagno Vignoni offer restorative soaks in ancient travertine pools just minutes away.
Drive twenty minutes west across rolling cypress hills to Pienza for wheels of pecorino, or south to the fortress town of Radicofani.
Piazza Grande sits at the town crest, framed by the raw brick Duomo, Palazzo Contucci, and Palazzo de' Nobili-Tarugi with its open loggia.
Weekly Thursday markets at Piazzale Nenni sell Chianina beef cuts, seasonal porcini mushrooms, local chestnut honey, and fresh sheep ricotta.