Weekend in Montepulciano

The unfinished Renaissance cathedral on Piazza Grande. Plain brick facade hides a single-nave interior with a large triptych altarpiece by Taddeo di Bartolo from 1401.

Tip: Look up at the wooden ceiling — it's original 16th-century painted panels. The church is often quiet mid-morning.

A 14th-century fortress turned cultural space with a small permanent exhibition and a wine bar inside. The outer courtyard and ramparts are free to walk.

Tip: The free courtyard has a giant wine fountain (free pour for anyone who buys a glass). Taste the Vino Nobile here — it's cheaper than most enotecas.

A 16th-century Medici fortress with a large grassy courtyard and panoramic walks along the ramparts. Inside, a wine shop offers free tastings of local Vino Nobile.

Tip: The fortress grounds are free. For a proper look at the fortifications, walk the outer path that wraps around the walls. The wine tasting is free only for purchases.

A striking white travertine church designed by Antonio da Sangallo the Elder, sitting alone on a hill just outside the town walls. Its Greek-cross plan and clean Renaissance lines make it a landmark o

Tip: Go early morning to avoid tour groups and catch the light through the west-facing windows. If you have a car, park at the bottom and walk up the cypress-lined path rather than the road.

A striking Renaissance church just outside the old town, designed by Antonio da Sangallo the Elder. Built from golden travertine stone, it sits alone in a grassy field.

Tip: Walk through the olive grove path from Porta al Prato (15 min) rather than driving. Arrive at sunset for the glow on the stone.

The main square of Montepulciano, a Renaissance-era piazza surrounded by historic buildings like the Palazzo Comunale and the Duomo. It’s the setting for the town’s summer Bravio delle Botti wine-barr

Tip: Arrive just before sunset when the light hits the travertine stone and the crowds thin out. The view from the Palazzo Comunale tower costs a few euros but is worth it for a panorama.

Montepulciano’s unfinished Duomo, started in the 16th century but never completed – the plain brick facade contrasts with a rich interior. Inside, look for the large triptych by Taddeo di Bartolo and

Tip: The church is dark and cold, so bring a jacket even in summer. The best preserved work is the Assumption altarpiece in the right transept.

The main square, a sloping paved rectangle surrounded by Renaissance buildings including the Palazzo Comunale and Duomo. Used as a filming location for the 'Pleasantville' scenes i

Tip: Go late afternoon when the sun lights the brick tower of the Palazzo Comunale. Climb the tower for €5 if you want the best view over the Val d'Orcia.

A family-run winery on a hillside just below Montepulciano. The tasting room offers free entry to browse the shop and sample Vino Nobile wines without booking – though seated tasti

Tip: The free tasting at the counter is quick but includes three wines. For a proper experience, book the 15-euro guided tour in advance – it includes the cellar and a better selection. Walk down from the Porta al Prato gate in 20 minutes.

Small museum in the Palazzo Neri-Orselli displaying medieval and Renaissance art, including a terracotta Madonna by Andrea della Robbia and a wooden crucifix from the 1300s.

Tip: Entry costs €4. Ask at the ticket desk if the museum is running its free admission Sunday (first of the month, depending on season).