Family trip in August

From a logistical standpoint, I would suggest all your days in Athens be at the end. Saves making one extra hotel transfer to be back to Athens for the flight home.

You do want to do all of Athens at the end. It is an hour from the airport into Athens and much more efficient to do it once. 3 days also allows you to rent an apartment which you may enjoy with a family. That is what we did.

That means you want to fly to the island of your choice on the same day you arrive. We bought tickets on Aegean airlines scheduled a couple hours after our international arrival. It also is nice to get over jet lag on an island.

The only island of the ones you are thinking of I have been to is Naxos which would be a great choice. There are lovely beaches and hiking. We stayed in st george beach adjacent to naxos town. It was not the best beach (shallow) but convenient to other things. Naxos has a tourist infrastructure but I found it quite charming. Now we were there in May not August but people really went out of their way to help.

We hiked to the top of Mt Zas which is the tallest peak on Naxos. One thing that is lovely about Naxos is that there are beautiful beaches and mountains too. We visited other beaches, towns, and historical sites. There is a company that rents bikes but we never made it there as we were too busy (we were there four nights) with other things.

We rented a car for two days and didn’t find it that difficult to drive or find our way around. Parking was nearby our hotel.

My son told me that people he met said Milos was their favorite island.

I don’t think you could go wrong!

You do not mention which 10 days in August you will be there. Aug. 15 is a religious holiday in Greece and many families take that time (week/weeks/month) to go on vacation and/or visit family at their home village. This could make some of your travel "touristy" with Greeks on vacation. Some places may be booked up well in advance because of this holiday as well. Just something to keep in mind.

We will be flying into Athens August 25 and leaving Sept 4. So I was hoping some of the hordes of visitors and tourists would be clearing out by then?

Another important question is are any of these islands more affordable when it comes to accomodations than others? If so, that would make the decision easier!

Right now I'm leaning towards going to Naxos and Antiparos OR Milos and Folegandros.

But if someone makes the case for going to Crete for a week and can tell me the best base (since I know it's huge) and a good place to stay I'm all ears!

Yes--you will be there after the height of the summer season so you should be fine.

Given the time you have, I would recommend Crete--more sites to see and more variety of things to do. The islands are more for recreating and relaxing imho.