We are going in May for two weeks with our three young adult children, and my daughter's husband. My husband's brother will join us after three days. It is our first time in Greece so thought I would share our itinerary in hopes it might be helpful. Some of our group have extensively traveled but two have never been to Europe. We also have a mix of interests and I tried to accommodate that.
We decided the Rick Steve's itinerary was too much driving with a group.
We are flying to Athens and then to Santorini that day. We are staying there three nights. Then we are ferrying to Naxos where we are staying four nights. My husband's brother who has been to Santorini and had no desire to return will join us there. He has traveled several times to Greece and we thought he would be a nice addition.
We are flying back to Athens and renting a van and driving to Nafplio. We will stay there four nights.
Then we will drive back to Athens airport and drop off the car and spend last three nights in Athens.
We choose Santorini because of its beauty and felt like we wanted to see it once even though it is very tourist ed. It does not have good beaches though and I was looking for a nearby island (in same island group for ferries) with good beaches for my crew as I knew that was important to them too. It turns out Naxos has an excellent combination of beaches, mountains, historic places, and charming towns. I picked Nafplio because it is a beautiful town on the sea and is close to several important ancient sites (e,g., Epidavros, Mycenae). It also is only a couple hours from Athens and I wanted to minimize driving.