Italy
The occultist Cagliostro died a prisoner in this fortress, in a cell entered through its ceiling.
The fortress looks impossible from below: a sheer-sided crag with battlements growing straight out of the cliff edge. One road, cut into the rock, reaches the village. From the walls, the Montefeltro rolls away toward San Marino and the Adriatic haze.
San Leo guards a spur above the Marecchia valley, refortified in the 1470s by Francesco di Giorgio Martini for Federico da Montefeltro, who had retaken the rock in 1441. As a papal prison it received Count Alessandro di Cagliostro, occultist, forger and celebrity of pre-revolutionary Europe, who died here in 1795 after years in the Pozzetto, a cell entered only through a trapdoor in its ceiling. Visitors still peer down into it. Below the fortress, the village keeps a Romanesque cathedral and an older parish church in golden sandstone, and Dante names the climb to San Leo in the Purgatorio.
Solo
Cagliostro's cell, the Romanesque churches and the fortress walls fill unhurried hours high over the valley.
Couple
A fortress village suspended above the Montefeltro feels both intimate and improbable; stay for the golden hour on the stone.
Friends
Fortress ramparts, a legend of a caged con artist and an osteria afterwards make an easy group day from Rimini.
Passatelli, breadcrumb-and-parmesan strands pressed straight into broth, are the Montefeltro's comfort dish.
A piadina off the griddle, folded round local cured meat, fuels the fortress climb.

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