Of the six cities – states dominant on the island in antiquity, Eressos was the one that had built the most observation – citadel towers for its defence against imperialistic Mithymna. The Trail circles all the locations inhabited by the ancient Eressians, the hub of Eressos, home of archaic poet Sappho and of Theophrastus, a naturalist, pupil of the great Aristotle. The start is at Skala and it heads west to the end of the beach where the ruins of Afentelli monastery are located. The ascent to the two chapels compensates the trekker with a spellbinding view. Each step holds a revelation, either on the hard rock or the plains. Moving clockwise, the circle ascends to the top of the ancient acropolis with its two medieval towers and the reservoir. The ‘Vigla or Mastos’ acropolis, very close to Skala and the sea, is crisscrossed and surrounded by trails in every direction.