The insider’s tour of the Tuscan city at the heart of Renaissance painting

Ten kilometres east of Siena, a mound rises above a Tuscan valley studded with stone-built farmhouses. It’s a scramble to the top of the tumuli (or burial mounds), but it’s worth it: looking to the horizon I can see the silhouetted outline of the city’s still largely extant medieval centre.

Behind me, among the cypress trees that crowd the summit, I find an obelisk memorialising the death of more than 30,000 men who fell when Florence tried and failed to defeat its rival city state at the Battle of Montaperti in 1260. That’s a long time ago, but for some, history still rankles, and if you’re the kind of traveller who likes an ancient gripe as much as an ancient building, then Siena – pitted against its neighbour for centuries – is the place to be. And it’s not just Montaperti that irks – there’s the Renaissance as well.

Ever since the virulently pro-Florentine 16th-century artist and writer Giorgio Vasari drastically downplayed Siena’s importance, art historians have been giving Florence the credit for starting the Renaissance.

But as will become clear in a revelatory new show at the National Gallery in London, featuring artists like Duccio, Martini, and the brothers Ambrogio and Pietro Lorenzetti – with works reunited, in some cases, for the first time in centuries – it was the emergence of a new kind of painter in 14th-century Siena that enabled the revolution.

All of them were encouraged by an enlightened merchant republic governed by a revolving council of nine, which treated painters as artists rather than artisans. Back in town, I find rich evidence of this at the staggering brick and stone headquarters the republic built, the Palazzo Pubblico. Finished in 1310, the Palazzo is one of the wonders of medieval Europe, and once I’ve got the Tuscan mud off my boots, I head inside for two more vistas.

First from the front, which overlooks the scallop-shaped Piazza del Campo, where the Palio horse races are run every July and August between the city’s districts (contrade). Then, from the back of the Palazzo, an open terrace looks out across fields. This was where the nine, who were not permitted to leave the building for the duration of their year in office, would come to check the republic’s crops were all in good order, knowing that behind them the painters were hard at work embellishing the Palazzo’s walls.

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The painters’ work is still there, and soon I stand gobsmacked in front of Simone Martini’s huge 1315 fresco Maesta, in the Palazzo’s Sala del Mappamondo. Taking up an entire wall, it shows the Virgin Mary in her majesty beneath a canopy attended by the saints. But only a staircase away from the Maesta, in the Chamber of Nine where the ruling council would meet, another work even better exemplifies this new relationship between authority and art: Ambrogio Lorenzetti’s series of frescos titled the Allegory of Good and Bad Government, painted between 1338 and 1339.

I’m funnelled with other visitors up the staircase, but our chat falls away when we emerge beneath Lorenzetti’s masterpiece, each of us coming to the hushed realisation that we have entered a magical portal to the 14th century and its social and philosophical aspirations. One side of the room shows a rural chaos peopled by devils, the other a happy and industrious populace going about their business in the ochre-brick and grey-stone streets, or making merry with tambourines.

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The Sienese today live, work and study in pretty much the same medieval city, spread along an axis between the Franciscans at the Oratorio di San Bernardino and the Dominicans at the Basilica Caterina San Domenico church, a huge brick barn erected in the early 13th century. Navigating around this axis, I stumble upon the bone-white 13th-century Duomo (cathedral), which is on the pilgrim route to Rome, along with the Pinacoteca Nazionale, a wonderful museum in a former palazzo dedicated to Siena’s late medieval and early Renaissance art, and finally my hotel, the sublimely old-school Grand Continental.

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This is another former palazzo, and the only five-star hotel within the city walls. From my room, I can see the Duomo and the Basilica Caterina San Domenico balanced on top of the steep ridge I’d seen from Montaperti. Just how steep becomes clear later on: having been tempted down plunging alleyways by the smell of cooking, I return sated by pappa al pomodoro and ravioli stuffed with ricotta and herbs, and have to clamber back up past street-corner flags that mark the territory of the contrade.

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I end up, as all visitors do, back at the Piazza del Campo, sipping a contemplative digestivo in a happily thronged bar and considering all those thousands of bricks before me. Even when it’s littered with tipsy revellers, it’s a space that, like Lorenzetti’s Allegory of Good and Bad Government, seems to embody all the admirable civic virtues of medieval Italy. All it lacks is tambourines.

Siena: The Rise of Painting, 1300?-1350 is at London’s National Gallery from 8 March until 22 June 2025