Itinerary check!

I would do 5 nights on Crete, maybe 3 on Santorini, and distribute the others as wanted. Perhaps Athens and day trips out?

The only islands Rick steves describes are Mykonos, Delos, Hydra, and Santorini. For information on Crete, try “The Rough Guide to Crete” and/or “The Lonly Planey Guide”to Crete”. (Other opinions from other posters are), Crete seems like a separate country (even though it is in Greece). For the other islands, try looking at “The Rough Guide to Greece”, The Lonely Planet Guide to Greece), possibly Frommers or Foddors guides to greece; books on history or travel writing, and so on. My current preference for myself is to write an approximate day-by-day itinerary listing two or three major activities each day; such an itinerary may help you figure out how much time you really need at each place you listed. For example, are you really going to have enough to do on Naxos to occupy you for 5 nights/4 whole days? Do you know what is on all the islands you list? Not that I know that there is anything wrong with these islands. I actually have never been to Greece but I am going there in October or possibly at the same time you are going but I am sticking with sites listed in Rick Steves Guide and there is not time for me to see everything and my interests are monuments, historical sites, museums, instead of beaches, special food, and so on.

Thanks jkelmam, I was hesitating with Numbers of nights in Crete. Doing 3 nights in Santorini, so are you saying that we should do are day trips from Naxos ?

Thanks Mike

Look at a good map of Greece & isles - http://www.explorecrete.com/crete-maps/images/greece.gif (click to enlarge). Santorini is too far from other islands to do a good day trip... and regular ferry schedules are not designed with tourists in mind; they are designed for the needs of Greek residents -- so they don't go off early in the AM and return to "base" after dinner. For day trips, you need a co. that runs dedicated excursion vessels... and Naxos has one. http://visit-cyclades.com/day-cruises/naxos-cruises You can go to Mykonos/Delos one day... go to Paros or Antiparos on another ... OR y ou can take one of their sailboats to a trio of tiny islands. However -- do not neglect Naxos itself... a large scenic island with wonderful mountains, hill villages, ruins, farms, beaches galore.

We spent almost a month in Greece last summer, mostly on the Pellopenese Peninsula at the most historic sites, and returned along the Corinthian Gulf to Delphi and then Meteora. Our only island stop was on Hydra for the Miaoullia Festival. Hydra was charming and the locals on the small boat we took to a beach on the far side of the island and for the fireworks the night of the festival were extremely kind to us. It is very touristy during the day as ferries drop people off for a few hours but like other tourist places, gets quiet after sunset. Though we loved Hydra, I am not sure it adds a lot to your itinerary unless you are a Leonard Cohen fan; if you do go, we wholeheartedly recommend the Orloff Boutique Hotel for its great service, quiet location, and impeccable rooms.
We definitely enjoyed Meteora and spent two sunsets staring toward the monestaries and the sinking sun. Because we were there on summer evenings, there were crowds at the best viewing spots. We organized a picnic for the second evening and got there early enough to have a prime spot for the view; we also brought a bag of cat food up for the picnic to share with the many strays who struggle to survive on human handouts (and the one who lived furthest from the monasteries turned her nose up to the cat food, preferring french fries and lamb to the food designed to keep her healthy--maybe she knew life is short). There is a long stretch of road when you get north of the Osias Loukas Monastery (coming from Delphi) and the ride from Meteora back to Athens is also pretty long without a lot of scenic stops, so you may want to consider the train though it would certainly be more cost effective to go by car as a group of 4. The roads themselves are in excellent condition though you will pay tolls along some stretches; and we were glad to have a car to drive to the monasteries. We stayed at Pyrgos Andrachti where, again, the service and food was excellent and we had a long discussion with the owner about the struggles of the feral cats that live in the hills; we also gave him the rest of cat food.

We thought Meteora was amazing but we also thought the drive along the Corinthian Gulf to Delphi and the ski towns to the east of Delphi were also high points of the trip. And we were positively surprised by the ancient Olympic ruins not far from there. So as you plan your trip, you might want to add a bit more history to your itinerary. We did a few beach visits but found that the waters were colder than we enjoy; even at one of the world's most beautiful beaches. On Hydra, there wasn't much more to do than wander the small town and go in the water, so you may want to evaluate what is drawing you to the islands, especially as temperatures cool in September and October.

We truly did enjoy the time on the Peloponnesian Peninsula, at Nafpoli, Mystras and the area near Kalampaka (we were extremely disappointed by Momenvasia, but there was so much to see in other area) and felt like the small villages and BandBs where we stayed were delightful and gave us a sense of life away from the big tourist towns of Greece. Also, driving outside Athens is easy.
Finally, let me recommend this amazing fast food place in Athens: OVEN SESAME, near Monstraki and the tiny little chapel....easy on your wallet with the crispest shells filled with incredibly fresh ingredients. Yum

Thank you all for your responses, it was very helpful.