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Which Greek Islands do you Love?

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This question is a spin-off of a question posted in the Lounge but I thought I shouldn't hijack the topic.

We are considering two itineraries in Greece. Some stops will be at a beach. Others will give time to wander around the port in the evening. Pro and cons of each set?

#1 Kea, Delos, Mykonos, Santorini, Crete, Kythira, Monemvassia, Nafplion, Hydra

#2 Ios, Santorini, Patmos, Ephesis (I know that's in Turkey), Samos, Delos, Mykonos, Tinos, Kea, Sounion

So which would you prefer and why?

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