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Anek ferry from Heraklion to Santorini........

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and Blue star ferry from Santorini to Rhodes

For beginning of May, how soon do I need to get tix? Is there advantage in buying early online? Can I wait till I get to Chania? Will have my laptop with me, should I go through an agent?
I read the ferry departs early. I am thinking I can drive there with a rental car the day before, do some sightseeing on the way and spend the night either somewhere close to the ferry terminal or.....? What would you recommend for sight- seeing and spend the night? What car company allow drop off at a different location?
I think I read I should buy all the insurance policies that comes with car rental in Greece. My credit card comes with some of that stuff but I guess I should buy the whole package anyway, is that the case?

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