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Hotel Reservations Needed in July?

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My husband and I will be traveling the Cyclades the first week of July. We have made reservations in Santorini for the first few nights and then most likely we will be taking the ferry to another island. However, we are having a hard time deciding where we want to go after Santorini and how long we are going to want to stay. We would like the flexibility of not making hotel reservations in advance for our second destination. We are thinking of possibly going to Milos, Paros or Naxos. Do you suggest making reservations for July in advamce or is it ok to wing it?

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