We have never been to Greece before and are starting to plan to go October 9, arrive the 10th. We like to take walks/hikes and see history, ruins and some museums. Don't need fancy restaurants, just good food, we don't drink alcohol, still water only. Love to watch the sunset and I love a good swim. Also we will need to buy distilled water on arrival in Santorini-google search has told me that people haven't reported if they found it in the stores or not.
We also could go the first two weeks of August, but wondering if heat might be too much. We have done Italy in July 95+ temps 5 years ago so understand heat. I do like to swim and it appears I can still get in the ocean mid October. No one has a crystal ball and the only big concern I have is whether everything gets shut down again by early fall.
We are thinking of flying from PDX to Santorini then fly home from Athens. Looking now at 3 nights Santorini - I know but as my husband said- if you never go back will you regret not seeing it, yes, yes I will. We will do the walk from Fira to Oia. Also maybe a tour of the island if we don't rent a car. Then 3-4 nights Naxos. We have no real plans here, need to research more. Walking/ruins and beach time. Then fly back to Athens and then go to Nafplio for 3 or 4 nights. Interested in Epidaurus and Mycenae. Again, how long to see things here? Then back to Athens for 3 nights. To see the usual suspects, as much as we can fit in.
I would like to know which destination to give the extra night to and if predicted weather for October will prohibit us from doing the above lists. I also will be interested if you guys know of personal tour guides that we could use in Athens and/or site by Nafplio. As I have said many times of our Italy trip the only thing I regret not doing is hiring a personal guide for Pompeii, we just used the audio guides and it felt like we missed things, it was just too big maybe. But we did just use the RS book for Herculaneum and we enjoyed it.
We are also wondering, rent a car or not -no car in Athens for sure, but the islands I don't know. I think it will be easier to do Nafplio with a car and probably Naxos. Weather appears to be cool to warm and possibly some rain for October. Anything I am totally missing for first trip to Greece? There will be lots of questions later after we have some tickets purchased. Thanks for any input now.