For those travelling on foot, there’s no real way out of Positano that doesn’t involve climbing steep stone staircases – lots of 'em! The advantage of this particular circuitous route is that it enjoys a bit of shade in its early stages as you plod heavenward amid a thick and gnarly holm-oak forest.
The walk starts on the main coast road (SS163) close to the Montepertuso turn-off by a ruined building and climbs steeply through trees before breaking into dryer Mediterranean scrub higher up. The coastal views open out as the path (#333a) traverses the hills above Positano with the hulk of Monte Sant’Angelo standing sentinel in the background. Turn left 2km up the ascent and then right at the top to join a wider trail towards the hike’s high point, the tiny village of Santa Maria del Castello (670m) is accessible by diverting along a narrow, paved road. At this ancient crossing point around 5km into the hike, you’ll find a small bar and a church. Take the narrow road back down to the main path; turn left (trail #333), proceed around the headland and then head right on a path that leads steeply down via a series of well-constructed staircases to Positano, visible in all its glory directly below. The walk ends beside the Bar Internazionale in Upper Positano. The total distance is 9km.