The narrow lane that runs along the back of the town just inside the southern wall. Pius II planned it as a panoramic promenade with intermittent openings onto the Val d'Orcia; the local nineteenth-century habit of using it for assignations gave it the names that have stuck — Via dell'Amore, Via del Bacio, Via della Fortuna.
Walk it at sunset. The view from the wall takes in Monte Amiata, the white roads of the Val d'Orcia, and (often) the cypresses of the much-photographed Gladiator scene at the bottom of the valley. The walk takes ten minutes and is the single best free thing to do in Pienza.