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Starting to Plan a trip to Greece - a few questions

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I think I've outlined the bones of a 2 week trip to Greece and I'd like a little feedback, if possible before I move ahead. So many informed users on this forum! So let's see:
1) I'm thinking of going the first 2 weeks of June. I figure it's before high season, weather should be good - sound okay?
2) Itinerary-wise - Athens (maybe some side trips), I'm not sure how many days to allocate here; then 3 islands - I'm thinking Naxos, Santorini and Rhodes. Maybe adding in Turkey, but might be too much for 2 weeks. I thought it might work to start in Athens, fly to Rhodes and then ferry my way back. Does this sound do-able? Good choices?
3) Transportation - we'd probably rent cars on Naxos and Rhodes, maybe Santorini too. Reasonable?
4) I usually plan and book everything myself, but I've seen many folks (and Matt) recommend using a Greek travel agency, I guess I looked at Fantasy. I COULD have them handle the inter-island travel only, or see if their hotels are okay. Is there advantage to using a local travel agency, or if I'm used to planning trips myself, should I just go for it?
5) How far in advance do I need to book for that time of year? Generally I get my international airfare done first, which nails down my dates. I usually would start looking after the first of the year. Soon enough?
6) Language - should it be a big issue for where we're going? I'll do some studying ahead and bring a phrasebook, but is English pretty prevalent?

Thanks in advance for any help/advice,
Alice

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