San Leo

Most people in this part of Italy are heading for Rimini and the beach, or up the road to the curiosity of San Marino. We turned off for San Leo instead, on the recommendation of a man in a Sant’Agata wine bar who said, with great seriousness, that it was the most dramatic town in the region and that Dante had mentioned it. The road up is a series of switchbacks that left Lia gripping the door handle, because San Leo sits on top of an enormous monolithic spur of rock with sheer cliffs on every side — a town you can only reach by the one road, and which for most of its history could be sealed off entirely.

The town on the rock

The town itself is small and stony and genuinely old, a piazza with two of the most important Romanesque buildings in the region facing each other: a ninth-century parish church and a twelfth-century cathedral, both built from pale local stone, both far grander than a place this size has any right to. We sat in the piazza with a coffee while a wedding party assembled on the cathedral steps, and the whole scene — the old stone, the green Montefeltro hills falling away beyond the cliff edge, the absurd defensibility of the location — felt like something staged. It is the kind of place where you keep stopping to look back over your shoulder.

San Leo’s whole existence is dictated by that rock. It was a strategic fortress for over a thousand years, fought over by popes, Montefeltro dukes, and the architect-engineers of the Renaissance, and the great fortress on the summit was redesigned in the fifteenth century by Francesco di Giorgio Martini specifically to withstand cannon. You climb to it on foot, and the view from the ramparts runs across the whole of the Montefeltro toward the Adriatic on a clear day, with San Marino’s towers visible on the next ridge.

The prisoner at the top

The fortress is most famous, though, as a prison — and specifically as the place where Giuseppe Balsamo, the self-styled Count Cagliostro, was held until his death in 1795. Cagliostro was the great occultist-charlatan of eighteenth-century Europe, a peddler of elixirs and Egyptian freemasonry who conned half the courts of the continent before the Inquisition caught up with him. His cell at San Leo, called the Pozzetto, was a special cruelty: a stone room with no door, entered only through a trapdoor in the ceiling, with a single barred window positioned so he could not avoid seeing the two churches below. I stood in that cell and found it genuinely chilling — a punishment designed by people who understood exactly what would torment a man who had built his whole life on illusion.

We ate lunch back down in the piazza — a plate of local prosciutto and a formaggio di fossa, the cheese aged in pits, that the waiter insisted was the only thing worth ordering — and I kept glancing up at the fortress on its rock. There is something about San Leo that stays with you: the sheer improbability of building a town up there, the layers of popes and dukes and charlatans, the cliff edge always at the corner of your eye. It is barely an hour from the beach crowds of Rimini, and it feels like a different century.

When to go: Spring and autumn for green hills and comfortable walking up to the fortress. Summer is busier and hot on the exposed rock, though still far quieter than the coast. The cathedral, parish church, and fortress all keep separate hours — check before you climb, and allow a half-day to do the town justice.