We have hiked over to the beach on the other side of Spetses for several years now. It takes 1.5-2 hours at a leisurely pace and I think most family and friends know the route now by themselves. About 15 years ago someone painted discreet red dots on the rocks to indicate the route. The dots have mostly faded or become covered in moss, but its not too difficult to remember without them.
We usually get going early, around 7-7.30 am to avoid the sun on the ascent up to the ridge behind Agios Vassilis church. Its a steepish climb for about 20 minutes through the pine forest, and then a gentle climb up to Panagia Daskalaki, an abandoned monastery/church set among the trees. There are really pretty views from up there and we usually take a breakfast break as a reward for the climb.
The church itself is kept in pristine condition and visited on its saint day each year and there’s even still a functioning cistern full of fresh water. However the living quarters have long fallen into ruin. When we first visited about 15 years ago, the kitchen area still had a roof, and the sleeping quarters had a dangerously caved in roof still in place. Now the sleeping quarters are just a roofless shell.
After Panagia Daskalaki the trail leads to the wide ridge road that runs like a spine down the centre of the island. From there onwards its a mostly gentle, winding descent to Anagiri beach. The trail used to be well shaded with pine trees, but about 12 years ago a major fire ravaged the back side of the island and now its just an open and dusty trail. A shame, of course, because the trees were so pretty, but also unfortunate because it means that the hike back is only for crazy people who can handle 100 degree plus direct sun beating down on a slow, dusty ascent. We take the bus back!