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Greek Islands in May 2011

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My boyfriend and I are planning to travel to the Greek Islands from May 28-June 5, 2011. I would love some advice about the following:

1. What are the best islands? We live in NYC and are looking to get away from it all. We love good food and wine, but don't need to be in the center of a big party.
2. Is it easier/cheaper to book in advance through a travel agent? Or is it preferable to book on my own through expedia?
3. Do I need to buy ferry tickets in advance, or can this easily be navigated upon arrival to Athens?

Any and all advice is welcome! Thanks.

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