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Greek Islands Honeymoon- Help!

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I'm brand new to the forum but I was hoping for some help with my honeymoon itinerary. My fiancé and I will be heading to Greece in mid September. Our tentative itinerary is as follows:

-Sept 9th depart US for Athens.
-Arrive in Athens around 12 noon on Sept 10th. We plan to do minimal site seeing/relaxing on this day.
-Depart Athens by flight to Crete on Sept 11th

Here is where I start to get a little concerned/confused. We think that Chania Town area is where we would like to stay, specifically Giorgi's Blue Apartments. We plan on renting a car and staying for 4 nights. My main concern is how we would get from Chania Town to Santorini for the next leg of our trip. I have read that Heraklion Port is the closest port to Chania Town that will take you to Santorini. Would we have to get up extremely early to drive the 2 hours to Heraklion? If we had a rental car would we be allowed to drive it one way to Heraklion and drop it off? Does the ferry to Santorini run at all times throughout the day and would it have to be purchased in advance?

We already have reservations at the Andronis Boutique Hotel from September 15th - 19th which is in Oia. Is it easy to get from the port to OIa?

After Santorini we wanted a smaller, more relaxed island to end our honeymoon (from 9/19-9/22). I think we have tentitavely decided on Naxos by ferry. I have done a fair amount of research on Naxos but does anyone have any suggestions for us as far as what area to stay in? We enjoy nice beaches and don't need to be completely isolated. We aren't clubby people but do enjoy a couple of drinks and a decent time at night (which could even be found at the hotel if necessary.)

Finally, we will head back to Athens on 9/22 by flight, spend the day and night in Athens and leave for the US the next morning (9/23)

I know this is a lot of information and a bunch of questions but I was hoping for any advice I can get! We have never been to Greece and I just want to make sure our travels from island to island will go smoothly. If you see any holes in our trip or if you have ideas on how to make it better please let me know! Thanks in advance for everyone's help!

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