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Need Help with Greece itinerary in May

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I am going with my husband and 19 year old daughter to Greece the middle of May for 18 days. I would like to spend a couple of days in Athens and then divide the days between Mykonos, Santorini, Rhodes, Crete, and possibly see Hydra too. Do I have enough time to do all of this without feeling rushed? How many days would you reccommend in each place? What is the weather like then? How long will it take to make connections between islands? I know I am asking a lot, but even part of the answers will help a lot. I want to stay in some beautiful hotels. Anybody have any reccomendations? Thanks

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