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Crete trip in early September

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My spouse and I are planning a trip to Crete for end August/early September, and I need some guidance on what needs to be booked in advance. We will fly from Athens to Heraklion, then spend a week or so driving to Chania and beaches on the west. At the end, fly back to Athen from Chania. We will book a hotel for Heraklion and probably Chania, but I am wondering if we can 'wing it" along the way - such as Matala, Reythmno, and Palechora, etc?

I'm trying to balance some flexibility in the plans but don't want to stress out trying to find hotels.We are late 40's, experienced travellers and don't need super fancy digs. Last time we went to Create it was early spring and hotels were not a problem. But given the time of year, should we plan it all out?
Thanks for the help!

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