Each island has its own character and personality. Maybe get a guidebook on the Greek Islands and at least read the "highlights" section of each particular one. For example, Rhodes has a lot of history, Mykonos is a party island (I hear -- haven't been there), there's tons to do and see on Crete since its so large, Santorini is known for its dramatic scenery, and so on. Pick out what sounds best to you and research some more, then make your decision.
I would say in a 2 weeks you should be able to see at least four islands without hurrying. Most of the ferries are overnight ones, and budget it as your "hotel room" for the night. Of course, you may have a tougher time of it going from island to island, as lots will likely go to Athens and back...
When in Athens, stay in the Plaka district -- it's close to the sights and has all the amenities you'll need as a traveler.
worldwidemike
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