INTERNATIONAL FLIGHTS FROM GREECE
The whole thing gets more and more confusing.
During the summer season, international flights start from
Athens, Iraklio, Chania, Santorini, Mykonos, Karpathos, Rhodos, Kos, Samos, Lesbos, Skiathos, Kavala, Thessaloniki, Kalamata, Kefalonia, Zakynthos, Lefkas, Kerkyra.

Crete sounds right for you.

With kids I actually think you could skip Santorini in favor of some other (cheaper) islands. Maybe try to get a bit East -- Rhodes or Samos? If you ferry to (say) Paros from Crete you will probably go through Santorini and you'll get to see the cliffs from the ship.

I'd do a couple of days in Athens but what about some more mainland Greece? If you love nature and hiking that would seem right up your alley? Probably hard to think of getting inland when there's so much great swimming, etc. in July in Greece.

It should go without saying but probably skip Mykonos too.

For a smaller island after Crete, please, please do not go to Santorini. We felt like we had left Greece when we went there. Could not wait to leave! . Go to Paros or Naxos for a much better Greek island experience, especially with kids.

The OP didn't come back since more than a week.

Easiest way to go from Crete to Samos: plane vias Athens
Otherways take the Wednesday boat from Iraklio (dp 12.00) to Chalki (arriving around midnight), the Thursday morning (9.50) catamaran from there to Kos and change there to a Samos bound catamaran (Pythagorio ar 17.30).

Paros or Naxos would be a good choice. Rhodes and Samos seem good choices until you look at the difficulty of getting there from Crete without going back through Athens. There is a direct flight taking 45 minutes from Heraklion to Rhodes 3 days/week in summer, and prices look reasonable. The ferry from Heraklion to Rhodes takes 14 hours, and I wouldn’t want to do that alone, never mind with children.

It would be interesting to know what non Greek's consider to be a "Greek island experience", seeing that Santorini allegedly does not offer that. What should a tourist look for when they want a real Greek experience?

Good question, Odin! Maybe sitting on a car ferry all day, chatting with the heavy goods vehicle drivers? ;-)

As a one-time visitor, I certainly can't answer -- but I can say that Santorini was nothing like anywhere else I visited in my otherwise wonderful month in Greece. With the exception of Santorini, I experienced extraordinary hospitality and graciousness and generosity -- and I use the term "extraordinary" even though I've been treated well in just about every locatiion I've been fortunate to visit. Santorini was the only place in Greece where I was treated poorly, and not just by one person.

I encountered kindess there, too -- I don't want to fail to ackowledge that -- but unlike any other location I visited while in that otherwise astonishingly welcoming country, my experiences on Santorini included some very unpleasant moments.

My understanding -- which could well be mistaken -- is that the difference is because the vast majority of those who interact with tourists on Santorini (e.g., restaurant staff) don't live there; they come to Santorini specifically to make money from the tourists who flock there. And BTW, I'm not blaming them -- the Greek economy has been very difficult for many people, and taking advantage of the few opportunities that exist for earning a decent living seems perfectly understandable.

I'll be interested in seeing whether knowledgeable Fodorites can clarify or expound on these issues.

If you read through kja’s excellent trip report, you will see she travelled to many places on mainland Greece not often visited by Fodorites. I’m certain that during her trip she had many opportunities to interact with Greeks who aren’t involved with the tourist industry.

The thing that surprised me the most about Santorini was the number of American accents I heard on the island, and I’m American born myself. Many seasonal workers on the popular tourist islands aren’t even Greek. My previous reply was tongue in cheek, but if you want a real Greek experience do like crazyh does and visit less touristy islands off season, or go to the mainland.

Hi Everyone. My apologies for disappearing. A house full of sick kids wasn’t conducive to trip planning. Thank you for all of the valuable info. Many of you have helped me plan previous trips and i can’t thank you enough.
I have now been able to narrow the options down to Naxos or Paros. They both seem reasonably accessible by ferry from Crete. Greece is so large that we don’t expect to even touch on it in one trip, especially in the heat and summer crowds. We want to keep our travel distances short and simple.
Any specific suggestions on places to stay on Paros and Naxos would be greatly appreciated. We would prefer a small hotel as opposed to a house rental because we will only have a few nights. We are a family of 5 so often require two rooms which affects our budget. Total budget per night (both rooms) would be approx. $500 US. We would be looking for somewhere either on a beach or with a pool. That being said, if you have somewhere FABULOUS that is a bit more, please share. I have a special birthday while we are there so can probably twist an arm or two!!
As for flights, I do realize we cannot fly directly from Crete to North America and have checked flights carefully. While we may have to transfer in Athens or another European hub, that is fine. We simply don’t want to add Athens to the back end of our trip.
Thanks again everyone. Sorry again for the delay and have a great day!

@ Heimdall: Thanks! :blush:

"Many seasonal workers on the popular tourist islands aren’t even Greek"

Good point!
Many of them come from the Balkans or the Caucasus.
Some big hotels and restaurants engage waiters from the Western European countries where their guests come from.
But many Greek waiters too come from other parts of Greece and cannot give any reliable information about the Islands where they work.

The same is true for South Turkey and North Cyprus with a lot of hotel and restaurant staff coming from Kurdistan, Kirgistan, Tadchikistan, Usbekistan.....