A hill town so steep it seems to be climbing away from you, where every alley ends in a view of the Val di Chiana laid out like a painting.
I arrived in Cortona out of breath, and I mean that literally — the town sits on the flank of a hill so steep that even the parking lots have their own gradient, and the walk up from where I left the car felt like a small pilgrimage. Cortona has been inhabited since Etruscan times, one of the twelve confederated cities of that vanished civilization, and you feel the age of the place in the cyclopean stone blocks still visible in sections of the city walls — boulders fitted together without mortar, older than Rome, older than most things I have any real frame of reference for. The Medici eventually took it, as the Medici took everything worth having in Tuscany, and their fortress, the Fortezza del Girifalco, still crowns the summit.
Streets That Refuse to Be Flat
What struck me most was how the town organizes itself around its own impossibility. The main street, Via Nazionale, is the only one flat enough to be nicknamed “il Rugapiana” — the smooth wrinkle — and everything else is stairs, ramps, and alleys that switchback up toward the fortress or plunge down toward the valley. The Piazza della Repubblica, with its stepped stone staircase doubling as a gathering spot, is where I sat with a coffee and watched the town go about its evening ritual, the passeggiata, old men arguing amiably outside the bar and teenagers perched on the steps like it was any Tuscan piazza and not one of the most photographed towns in the region thanks to a certain memoir-turned-movie that put it on the map for English-speaking readers. I won’t pretend Cortona hasn’t leaned into that fame, but away from the postcard shops it’s still a working hill town with a butcher, a produce market, and a rhythm that has nothing to do with tourism.
The View That Explains Everything
The real reason to climb Cortona is the view, and specifically the walk up to Santa Margherita and the Fortezza del Girifalco at the top. From up there the Val di Chiana unrolls beneath you in a patchwork of cypress-lined farm roads and vineyards, and on a clear day you can see all the way to Lake Trasimeno shimmering in the distance toward Umbria — the site, incidentally, where Hannibal ambushed and annihilated a Roman army in 217 BC, a battle so total that Roman historians said the ground shook and neither side noticed the earthquake happening around them. Standing on that fortress wall with the wind coming up off the valley, I thought about how much history this small stretch of hillside has absorbed and how little of it shows on the surface — just cypresses, stone, and silence.
Cortona is also, unmistakably, Luca Signorelli’s town — the Renaissance painter was born here, and his work hangs in the Museo Diocesano alongside a Fra Angelico Annunciation that stopped me cold, the kind of quiet devotional painting that doesn’t announce itself but rewards anyone who actually stands still in front of it for more than ten seconds.
When to go: Late September into October, when the grape harvest is underway in the valley below and the light turns the stone the color of honey; August is beautiful but the town fills fast, and those stairs are no fun in the midday heat.