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Connecting flight from Athens to Crete and car rental 'issues'

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We will arrive in Athens airport on a Saturday at 12 noon. We plan to take the flight to Chania, Crete that departs at 2:20pm. My first question - is this enough time to factor in minor delays, get our bags and over to the gate for the 'puddle jumper"?
Second question - the plan is to fly to Chania and rent a car. A few days later drive the car to Herkalion and leave the rental car at the Herkalion ferry terminal. Because, we are taking the ferry to Santorini. Will the car rental agency let us do this? (and not charge us a premium?). Or should we fly into Herkalion and rent the car there? We are visiting both
Herkalion and Chania.
(sorry for the confusing post, but I think a lot of you are used to reading posts like this)

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