Odds are your most memorable experience won't be planned or expected.
My most memorable experience in Greece was hiking to the top of Skaros Rock- not on the trail but climbing the actual rock- in Santorini to watch the sunset.
As far as things not mentioned in guidebooks go, we hiked to the top of a mountain in Lesvos to picnic at a small church on top but I cannot remember the mountain's name. We started hiking past this aqueduct though: http://www.greeka.com/eastern_aegean/lesvos/lesvos-excursions/roman-aqueduct-moria-lesvos.htm
Lesvos itself was very untouristy while I was there because of the refugee crisis.
My favourite island is Lesvos/Lesbos... unspoilt, very local, very few tourists (mostly in the north) and very green. We would love to go back but held off for now because of the refugee situation. We were there before the Syria crisis.
Also, I am a Greek Islands fan... I (together with my partner) go every year each summer to the islands and picking each time a different/new island. When we finally retire, we will be staying longer than our usual 2-week vacations.
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