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Greece in May or August/September?

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I've read a few of the topics in this thread, but haven't finished reading them all. Apologize if I'm asking the same question. We're trying to decide when to travel to Greece. We're thinking either late May or Aug/Sept, because we want to go during shoulder season to get better prices and less crowds.

My husband, myself, and a friend of ours are planning a 1 week trip to Greece and 1 week to Turkey. We're thinking to go to Athens, Santorini, Mykonos (not necessarily in that order). To save time, we'll probably get cheap flights between Athens and the islands because the ferry rides seem really long. We're in our mid-thirties and planning to get a Triple room. When I looked at some hotel prices for Santorini and Mykonos, it seems that the prices are half the price in May compared to Aug/Sept. A friend of mine told me that the water at the beach on the islands is too cold in May. But if the price difference is so big, do I even care if the water is too cold? And how cold are we talking about, freezing cold like Los Angeles beaches? Can I still wear shorts around that time?

Average weather for Santorini is low of 65F/high of 75F in May. For Houston (where I live) 65-75 would be nice weather, but maybe things are different in the islands.

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