Montepulciano discovery guide

Piazza Grande at the top of the climb is the best square in southern Tuscany — a Michelozzo palace, a Sangallo-or-Vignola palace, and a cathedral of 1594–1680 that was never given a façade and still shows raw brick. Below the walls, the Madonna di San Biagio of 1518–1545 stands alone in a field and is one of the most complete High Renaissance buildings in Italy.

The friction is the gradient. Montepulciano is a 605-metre ridge and the town is one long ascent from the gate to the square — the hardest walking of the five towns in this group by a clear margin. In August it is punishing.

The smart way is to take the climb in the morning, eat at the top, and come down slowly. Then drive five minutes to San Biagio rather than walking down to it and back up. And order the Vino Nobile knowing it is Sangiovese, not the Abruzzese grape of the same name.

What the year does

Montepulciano is at 605 metres — the highest town in this group — on an exposed ridge, and the climb is the thing the season acts on.

• January–February — cold and windy on the ridge, with fog in the valleys on both sides. Quiet, cheap, and the cellars receive by appointment. The climb is pleasant when it is cold.
• March–April — the valleys green up on both sides. Good walking weather and the first visitors.
• May–June — the best weeks. Warm but not punishing, long evenings on Piazza Grande, the cellars unhurried, San Biagio at its best in the late light.
• July–August — hot, and this is the one town here where that genuinely matters: the main street is a continuous climb with little shade, and midday in August is hard work. Walk up before 09:00 or after 18:00.
• Last Sunday of August — the Bravio delle Botti. The town is full, the barrels go up the hill, and nothing else is happening. Book months ahead or avoid.
• September–October — harvest, and the best combination of weather and quiet. Clear air, warm days, cool nights.
• November–December — the new vintage in barrel, bare valleys, low light and very few people. Christmas brings the town out onto its own square.

If you have one visit: late May, early June, or late September. Avoid an August midday whatever else you do.

Take the climb deliberately

Montepulciano is a single ascent and the right way to see it is to walk the whole thing from the Porta al Prato up to Piazza Grande, slowly, stopping. The main street — called the Corso — rises past Renaissance palace fronts the whole way, and the point is that the town gets grander as you get higher. Allow an hour and a half going up, not twenty minutes.

Piazza Grande

At the top, and worth sitting in. Four things define it. The Palazzo Comunale, designed by Michelozzo — Florentine, austere, and deliberately reminiscent of Florence's own town hall, which is a political statement about where Montepulciano's loyalties lay. Palazzo Tarugi, attributed to Antonio da Sangallo the Elder or to Vignola. The Palazzo Contucci, with a historic cellar beneath it. And the Duomo, built 1594–1680, whose façade was never finished — the brick is bare, and it is the most honest thing in the square.

The Madonna di San Biagio, which is the reason architects come

Below the walls, five minutes by car or twenty minutes down on foot. Designed by Antonio da Sangallo the Elder and built between 1518 and 1545: a Greek-cross church in pale travertine, standing by itself on a platform in open country with nothing built against it.

That isolation is the whole point. High Renaissance architects wanted centrally planned churches to be seen in the round as free-standing objects, and almost nowhere did they get the chance. Here they did. Go in the late afternoon when the travertine goes gold, and walk around the outside before going in.

The cellars

Several historic cellars are cut into the rock beneath the palaces on the Corso, and they are open. This is the easiest serious wine tasting in Tuscany, because you walk to it. Ask for Vino Nobile and Rosso di Montepulciano side by side — same grapes, very different release rules.

If you are here on the last Sunday of August

The Bravio delle Botti — the contrade of the town racing barrels uphill through the streets to Piazza Grande. It has run on that day since the 14th century. It is one of the few Tuscan festivals that is neither a reconstruction nor a performance for visitors.

Montepulciano is a Florentine town in Sienese country, and once you know that, the architecture explains itself.

From 1390 Montepulciano was a loyal ally and then a possession of Florence, in a region otherwise dominated by Siena — and it stayed that way until 1559, when Florence finally took Siena itself and this town stopped being strategically useful. For those hundred and seventy years Montepulciano was Florence's forward position, and Florence paid for the buildings.

That is why the Palazzo Comunale on Piazza Grande is by Michelozzo — Cosimo de' Medici's architect — and why it looks like a smaller, plainer version of the Palazzo Vecchio. A hill town in Siena's backyard with a Florentine town hall is making a statement, and it is not a subtle one. Palazzo Tarugi, attributed to Antonio da Sangallo the Elder or Vignola, belongs to the same imported-prestige tradition.

The second thing worth noticing is the unfinished Duomo. Built between 1594 and 1680, and its façade was never faced: it is raw brick on the grandest square in the region. Towns usually hide that sort of thing; Montepulciano has simply lived with it for three and a half centuries, and the square is better for the honesty.

The third is the Bravio delle Botti, run on the last Sunday of August since the 14th century: the town's contrade pushing heavy barrels up the hill to Piazza Grande. A race that is deliberately, absurdly hard, up the same climb every resident makes daily, is a very exact piece of civic self-knowledge.

And then the wine and its confusing name. Vino Nobile di Montepulciano is a Sangiovese red — minimum 70% — that has been a DOCG since the 1980 vintage. The Montepulciano grape is something else entirely, grown mainly in Abruzzo. The town has spent decades explaining the difference and is slightly weary of it.

Montepulciano is a working town of 13,984 people — large enough to have its own life, which changes what responsible visiting means here. It is less about load than about where you spend and how you treat the hill.

• Eat and drink above the first two hundred metres. The lower stretch of the main street, nearest the car parks and the coach drop, is where day visitors stop; the upper town, where the climb has thinned the crowd, is where the residents are. Both the prices and the cooking are better up there.
• Buy Vino Nobile from a producer in town. Several of the historic cellars are cut into the rock under the palaces on the main street, open to visitors, and buying in one of them puts the money directly with the grower. Rosso di Montepulciano — same grapes, released from 1 March of the year after production rather than after two years' maturation — is the everyday bottle and far cheaper.
• Settle the driving. The cellars are in the town but the roads out are narrow hill roads, and the wine is substantial. Walk to a cellar from your hotel, or nominate a non-taster.
• Respect San Biagio as a church. The Madonna di San Biagio is an architectural pilgrimage site and also a working church in an open field with no barriers. Park where you are meant to, do not walk on the lawn platform where it is roped, and keep quiet inside.
• Come outside the Bravio if you want the town, or for it if you want the spectacle. The Bravio delle Botti fills the town on the last Sunday of August and has done since the 14th century. It is genuine and it is extremely busy; decide which trip you are taking.
• Walk, do not drive, inside the walls. The historic centre is restricted and the streets are steep and narrow. The climb is the experience.

What Montepulciano actually costs

Moderate, and better value the higher you climb. This is a town of nearly fourteen thousand people rather than a village, so it has a real economy and prices set by residents — except on the first stretch of the main street, which is where the day visitors stop.

The one piece of advice that saves money

Walk further up before you eat or buy. The lower Corso, nearest the car parks and the coach drop, is the tourist run; the upper town, past the hardest part of the climb, is where people live. The gradient does the filtering, and the prices follow it.

The wine, and the cheaper bottle

Vino Nobile di Montepulciano is Sangiovese, minimum 70%, with up to 30% complementary red varieties, and must undergo at least two years' maturation from 1 January following the harvest — with wood ageing of 24, 18 or 12 months depending on the option taken. A Riserva needs grapes of at least 12.50% natural alcohol and at least three years, including six months in bottle. DOCG since the 1980 vintage.

Rosso di Montepulciano is the money-saver: the same grape composition, but it may be released from 1 March of the year after production rather than after two years. A fraction of the price, and what most people here drink.

Several historic cellars are cut into the rock beneath the palaces on the Corso and are open to visitors — the easiest serious tasting in Tuscany, because you walk to it rather than driving.

The museums, and an honest gap

The town has a civic museum with a picture collection. We do not give its hours or prices, because its own website answered 403 from every path when this page was written and we do not publish operational details from anywhere but the operator. Ask at the tourist office or the municipality, 0578 7121.

What is free

• Piazza Grande and the whole climb to it, which is the main experience.
• The Madonna di San Biagio — the exterior, which is the architecturally important part, and the setting.
• The views off both sides of the ridge.