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Planning 2017 Greek Isles Trip

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I am planning a 12 day trip to Greece in June, 2017, and intend to spend approximately 10 days at approximately three islands and 2 days in Athens. Will arrive at Athens airport at approximately 0300.

The current flexible plan is to travel to Santorini as soon as possible and work my way back for the final two days in Athens. Not sure whether to fly or take ferry to Santorini. Intend to spend three additional days after arrival day in Santorini, next three days at an undetermined island and then three at Mykonos. The last two days will be in Athens, followed by a departure day.

As our party will include mostly first time visitors to Greece, I would generally like to visit popular, easily accessible tourist sites that will not take a lot of extra time to get to. For that reason, I would like to visit Santorini and Mykonos, but could rearrange (shorten) the planned time at these islands, particularly Mykonos. For the third island, I understand that Naxos & Paros are between these and make sense as a stop. But at the same time, without ever having visited Naxos or Paros, I would like to visit a laid back, relaxing, safe, authentic and of course beautiful island with beautiful beaches that is fairly easy to get to, and between Santorini and Mykonos. I don’t know if this exists, or if Naxos or Paros would fit the bill.

I am trying to create a firmer trip framework, but the trip is not for another 10 months. I am not sure when I will be able to make certain arrangements within Greece, so I have a few questions:

1) I am not sure about appropriate time frames for each location. Any suggestions?
2) In light of early arrival time and traveler fatigue, would a ferry or flight to Santorini be best? I understand that you can get a 4 person sleeping cabin on the slow ferry, which might leave at about 0730 and arrive at about 15:00, which would allow for some rest. Or would it be better to catch the earliest possible flight and get to Santorini as quickly as possible? You probably couldn’t check into a hotel until much later, so getting there quickly may not be such a benefit.
3) Will the prices of a sleeping cabin be similar to a flight? How soon can I book a flight or ferry? I cant seem to do so over the internet yet.
4) If I take a ferry, I understand that it may be best to take bus X96 from the airport to Piraeus, which may take about 45 minutes. Would a taxi be better? How much more would a taxi cost? Any suggestions?
5) If I fly, would it be from the same airport and when would the earliest flight be? The best airline?
6) How late can I wait to schedule inter-island ferrys? Can I do it over the internet?

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