I have been reading these forums and saw what great advice people have received and thought I would see if I could get some too.
We are planning a trip to Greece next year with our three children and my daughter's husband (ages 21, 25, 27, and 33). My husband and I have been to Europe a half dozen times, mostly recently last summer to Italy, but never to Greece. Both the 25 year old and 27 year old have traveled extensively in Europe as students (but never to Greece). The 21 year old and 33 year have never been out of the country.
We will have two weeks. I was thinking of flying directly from Athens to Santorini. That would get us there early evening on first day (a very long day but seems better than going to Athens first) I am thinking four nights there which would be three full days. On the afternoon of fourth day would take ferry to Naxos (leaves 3:30 pm). Spend evening, one full day, and two nights there. Then take ferry at 9:30 am on Saturday to Athens. It arrives at 3:00 pm. Take taxi to bus station to take 5:00pm bus to Nafplio. Spend four nights (three full days) there. Then take bus to Athens for last three nights (2.5 days).
We had thought of driving to Nafplio but don't want to coordinate two cars in a foreign country. We have been told that a van which would hold all of us is not a good idea on Greek roads.
I had dropped Hydra in favor of Naxos because of children's desire to see picture perfect greek beaches as well as fact on ferry route from Santorini. I also saw that ferry to Hydra was fast ferry and we took one from Naples to Sorrento last summer and not much different from being on an airplane.
My original intention was to stay in port town of naxos and just visit beaches for day to get that Greek beach experience but now have seen gorgeous hiking and am wondering about taking off a day from Santorini and adding it to Naxos. That would give us evening, two full days, and part of a third day in Santorini but we will be somewhat jet lagged (I will be in Greece earlier for a conference so one person will not be). My daughter suggested dropping Nafplio and spending more time on the islands but I am quite enchanted with Nafplio and think it would be a good place for a group. I am a bit leery of Santorini because of how touristed it is but have also heard it is quite beautiful.
We plan to rent houses or flats in Santorini, Nafplio, and Athens and stay in hotels in Naxos. There really aren't any rentals in port town large enough and hotels are inexpensive enough there. We will stay central so that people can do things without always having to coordinate.
I would be interested in whether it makes sense a) to spend one day less on Santorini and one more on Naxos b) whether it really is too much to try to go four places in two weeks in Greece. (It is 13 nights and 12 days in Greece, although we could go back on Sunday instead of Saturday and extend one day).