Porta al Prato to Piazza Grande — a Renaissance walk through the heart of Montepulciano

From Porta al Prato, the main street climbs gently through the town — a kilometer of Renaissance palazzi, artisan workshops, wine shops, and churches. You'll pass the Colonna del Marzocco (a Florentine lion on a column — Montepulciano was a Medici ally), the Torre di Pulcinella (a clock tower with a Commedia dell'arte figure that strikes the hours), and the Palazzo Bucelli, whose base is studded with Etruscan urns and cinerary pots embedded directly into the stonework. Don't rush this — the walk is the attraction.

The summit. Montepulciano's main square is one of the most harmonious Renaissance piazzas in Tuscany — the Palazzo Comunale (modeled after Florence's Palazzo Vecchio, with a tower you can climb for panoramic views of the Val di Chiana, Val d'Orcia, and on a clear day, Siena), the Cathedral (housing Taddeo di Bartolo's monumental Assumption altarpiece), and the Pozzo dei Grifi e dei Leoni (the well of the griffins and lions, designed by Antonio da Sangallo). Have an espresso at one of the piazza cafes and take it in.

• Comfortable shoes are essential. The climb from Porta al Prato to Piazza Grande is gradual but entirely on cobblestone — about 1 km uphill.
• The wine shops along Il Corso all offer tastings of Vino Nobile — resist the temptation on the way up. You'll get far better wines during the cellar tour and at Gattavecchi.
• Montepulciano was a filming location for Twilight: New Moon (the Piazza Grande chase scene). If anyone in the group cares, now you know.

Beneath the Renaissance — medieval tunnels, Etruscan tombs, and the birthplace of Vino Nobile

Montepulciano sits on a ridge of tufa — soft volcanic rock — and for centuries, the noble families of the town carved cellars deep into the stone beneath their palazzi. The result is an underground city: a labyrinth of Gothic-Renaissance tunnels, brick vaults, hidden crypts, and ancient wells running beneath the streets above. Inside the cellars, enormous oak barrels hold Vino Nobile di Montepulciano DOCG and Vin Santo as they age in cool, constant conditions.

Guided tours typically start from the Piazza Grande area and take you through two underground cellars connected by tunnels carved into the tufa. You'll walk beneath the noble palazzi — Tarugi, Avignonesi, Del Pecora, Batignani — passing through stone passages, medieval workshops, and authentic Etruscan tombs dating back over 2,000 years. The tour ends with a tasting of Vino Nobile, Rosso di Montepulciano, and often Vin Santo with cantucci.

• Medieval tufa tunnels — carved passages beneath the Renaissance palazzi, with spectacular brick vault ceilings.
• Giant oak aging barrels — Vino Nobile and Vin Santo resting in centuries-old cellars at constant cool temperature.
• Etruscan tombs — authentic 2,000+ year-old burial chambers discovered during cellar excavations.
• Medieval wells, workshops, and escape passages — used by Ghibellines during factional conflicts.
• Wine tasting — Vino Nobile DOCG, Rosso di Montepulciano DOC, and often Vin Santo with cantucci at the end.

• Bring a light layer. The cellars are cool year-round (~14°C / 57°F), even in June.
• The tour involves uneven stone floors and low ceilings in places — wear those good walking shoes.
• If you book the official Strada del Vino Nobile tour, it typically visits two cellars. Budget about an hour.

13th-century monastery · La Cucina di Lilian · terrace over the Tempio di San Biagio

Dave and Mike have been here before — and loved it. We got to know the Gattavecchi family through our good friend Alfio Morricone, and we're looking forward to bringing everyone back with us this time.

Gattavecchi is not just a restaurant — it's a family winery set inside the former Monastery of Santa Maria dei Servi, dating to the 1200s. The dining room occupies the old refectory, and the wine cellars below contain a 2,000-year-old Etruscan tomb discovered during renovations. The food is La Cucina di Lilian — traditional Tuscan dishes made by Lilian Gattavecchi, paired with the family's own Vino Nobile.

The terrace on the upper floor is the crown jewel: an outdoor dining space with panoramic views directly overlooking the Tempio di San Biagio — Antonio da Sangallo the Elder's Renaissance masterpiece, sitting in the green valley below the town walls. This is one of the great lunch views in Tuscany.

Pici all'aglione — fat hand-rolled pasta with a garlicky tomato sauce, the signature dish of Montepulciano. Bistecca tagliata — grilled sliced steak with arugula and parmesan. The family's own Vino Nobile di Montepulciano by the bottle — you're at the source.

• Ask about a cellar tour before or after lunch — Gattavecchi offers guided visits of their underground cellars, including the Etruscan tomb. It's separate from the town cellar tour and worth doing if time allows.
• If anyone wants to buy bottles to take back to the villa, the family shop has the full range at winery prices.
• The terrace faces west, so afternoon light is gorgeous. Bring sunglasses.

Antonio da Sangallo the Elder's Renaissance masterpiece — the church Michelangelo studied before designing St. Peter's

You'll have been staring at it from the Gattavecchi terrace all through lunch — now walk down to see it up close. The Tempio di San Biagio sits alone in a green meadow just below the town walls, and it is arguably the finest Renaissance church in Tuscany outside of Florence. Built from local travertine between 1518 and 1545, its perfect Greek-cross plan and honey-colored stone are stunning. Michelangelo reportedly studied Sangallo's design when drafting the first plans for St. Peter's Basilica in Rome.

The walk down from Gattavecchi takes about 10 minutes on a gentle road. The church is free to enter. You can drive back up to the P1 lot afterward (it's about a 3-minute drive), or walk back through town if the group has energy.

• This is the best place for a group photo — the church against the Montepulciano skyline is iconic.
• If energy is low after lunch, skip the walk and simply enjoy it from the Gattavecchi terrace. You've already seen it beautifully.