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Greece-Early Planning, please help

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My DH and I (60ish) are planning a trip to Greece for June 2014. We have never been. We want to see archeological sites, great scenery and have a combination of rest and activity. We have a timeshare trade booked for June 3 on Crete for a week and we need to be in Lake Garda Italy on June 27. Those are our only constraints. Here's a preliminary itinerary, starting at the end of May.

Fly to Athens, rest one day.
Mykonos 3 nights
Santorini 4 nights
Crete 7 nights (timeshare trade just west of Heraklion)
Ferry to Peloponnese, drive to Athens and tour as we go 5 nights
Athens 7 nights
Open- 5 nights What should we do?
Lake Garda 4 nights

Here's some question please:
We are only English speakers, will we have any difficulty navigating/driving on our own.
Do we need a car anywhere other than Crete and Peloponnese?
Would you change the number of nights anywhere? More or Less?
If we squeeze out more than 5 open nights at the end we'd like to go to Amalfi or Cinque Terre before Lake Garda. Enough time?
We plan to fly from Athens to Mykonos and take the ferry from Mykonos to Santorini; good plan?
Any recommendations on where to stay around $100 or less? Realistic budget?

Thanks for your help!

By the way, you may have noticed that I was asking a lot of questions about Ireland/Scotland for the same time. Now that I have it totally planned, we decided to save it for another time.

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