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2 Weeks in Greek Islands

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Hi, Guys,

I will be in Turkey and Greece for a month this summer, basicall all of July. Aside from 3 days in Istanbul, the trip will be centered on Greece (I've revised some previous plans that had me spending more time in Turkey for a variety of reasons).

For the first two weeks, I'm traveling with a friend and our schedules are set for Naxos/Milos/Santorini. After that, however, I have 2 more weeks by myself COMPLETELY UP IN THE AIR. I love being spontaneous, and the only other time I've been to the Greek islands, I had no itinerary, hotel reservations, or the like and it worked out perfectly.

My questions are these
1) Is it likely that I will be able to find some sort of accommodations on most of the Cyclades if I don't have reservations? It didn't seem to be a problem last time, also during late July/the high season, but if there are particular islands I should be wary of going to without a reservation, I'd like to be aware of that

2) For someone who will be spending most of his time alone and likely will want to enjoy beautiful beaches, churches, towns and hiking - what other Cycladic islands (or islands that are easy to reach from Santorini), would any of you more experienced travelers recommend? I think we've selected three great ones in Naxos, Milos, and Santorini, and I have no problem going back to one of them again during the same trip if I fall in love with it, but given what I am looking for - perhaps islands like Sikinos, Paros, or Amorgos might be good?

I thought about switching it up completely and traveling back through Athens to get to the Ionian islands on the west coast of Greece since they have a more lush, green landscape than the Cyclades and might provide more diversity, but not sure how easy and/or worthwhile that is to pull off.

Any suggestions for how YOU would spend 2 weeks alone in the Greek islands if big crowds/clubbing wasn't on your list of things to do?

Thanks so much for your input!

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