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Two 13 night itineraries: which would you do?

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Looking for advice on which itinerary (modified or as is) would be better for 13 nights in Greece.

When: Late May or June 2015.
Who: My wife and I (mid 30s) and our son (3). We like picturesque villages, kid friendly beaches, interesting cities, good food, strolls (out son loves walking as long as he can take an hour to go 3/4ths of a mile), and gorgeous views from our hotel. I love historic ruins much more than the rest of the family.

Previous Greek trips: None as a family. I went on a grand tour as a teenager: Athens, Delphi, Napflio, Naxos, Santorini. One goal of this trip is to go somewhere I haven't been.

Itinerary 1
Fly into Chania, 3 nights in town
Drive to central Crete. 3 nights probably at Eleonas in Zaros.
Ferry to Naxos. 5 nights.
Fly to Athens. 2 nights.

Or maybe go Crete-Santorini-Naxos and skip Athens. Is it feasible to fly Naxos - Athens and onward to N. America in the same day?

Itinerary 2
Fly to Santorini. 2 nights
Ferry to Folegandros. 3-4 nights depending on connections onward.
Ferry to Naxos. 4-5 nights depending on how long we spent in Folegandros.
Fly Athens. 3 nights.

Folegandros ferry connections seem a bit challenging but I like the idea of a off the beaten path island. Any alternative ideas?

Would the reverse work better for either of these? We would be flying in from Boston so most likely connecting in Athens to get to the islands.

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