please help with itinerary to Greek islands

Look at this map: http://tinyurl.com/22wfdvthtm

You will see that not all the islands you've mentioned are close together or in the same grouping.

If Santorini and Naxos are two must-see islands for you then you're better off going with Paros, Antiparos, Folegandros or Amorgos to hop without wasting too much time. All of these are great for hiking.

You can check for ferry schedules on http://www.gtp.gr but you won't find anything now for next May/June. You'll probably have to wait until April for that, with the exception of the schedules for the Blue Star ferries, which do come out earlier.

In my view, your plan to fly directly on to the most distant island at the beginning of your trip is a good one. Saving Athens for the end is good although I would plan two nights there. We flew directly on to Santorini. We had five nights there and loved it. We didn't go to Rhodes but we have always wondered if we should have. Use the Aegean Airlines website to explore connections. From Santorini, you can work your way back to Athens using the ferrys. Bluestar is the main one. Naxos makes a good contrast to Santorini. Mid-May is a good time to be there.

I've only been to two of the islands you mention but can assure you that you will enjoy your time there. We flew Athens to Paros, ferry to Naxos, ferry to Santorini and then flew back to Athens. Santorini is a must see, as everyone will tell you, and I am glad to have spent 5 days there - but I don't think I would go back. It's very expensive and it feels like a tourist stop. Most of the people we met there did not come from or even live there - they come in to manage the shops, restaurants and hotels for the tourist season and then go home to whereever it is that they live for the rest of the year. Naxos on the other hand has a very different atmosphere - it was our favorite island! You will find lots to do there and the people are very friendly and helpful. Check out the Venetian Castle Museum - they have concerts there in an open air courtyard. Naxos is greener island so you will find good hiking and touring opportunities as well as excellent beaches.

lots to do on santorini and rhodes but unless you like to lounge on the beach or plan to hike a lot i would do 3-4 days each. symi was beautiful, actually one of my favorite of the 10 we saw. nisyros is close by and was really interesting with its thermal areas. i would also recommend 2 days in athens. we were there only one and saw the acropolis and agora but didnt have time for the museum. sorry i cant help with connections between islands since we were sailing.

We prefer the islands near Turkey, specifically Samos. From Samos we day trip to Patmos and Ephesus, in Turkey. We also do Ikiara, Chios and Lesvos and then you can ferry to Turkey if you like. Boats are available from one island to the next daily or biweekly at a reasonable cost. Samos is full of vegetation so its an excellent place to hike. We found a small village at the top of a mountain that was locked in time. They originally journeyed to the top to avoid massacre and generations later they are still there.

Rhodes is wonderful! Really interesting. Try to rent a car for a day when you're there and drive along the east coast.There is a butterfly valley that is delightful and just driving along the coast is wonderful.
5 days in Santorini is a bit much unless you're really trying to relax. Can't imagine what you'd do with that much time.
Didn't see Crete on your list...Check and see if the archeological museum is open yet after it's refitting.

I think if you want to see Santorini, Naxos, Rhodes and Symi, you should do it! I agree that Rhodes and Symi look intriguing; we just started planning our first trip to these islands (plus Tilos & Nisyros) for September 2011; we'll then fly Sky Express to Lesvos (our personal favorite).

I'd recommend that you fly directly from Athens to Rhodes; take the short ferry to & from Symi, then fly Sky Express from Rhodes to Santorini, ferry to Naxos, and then ferry back to Athens for two nights (one full day) before your trip home.

I think 4-5 days is a little much for Santorini. It's very beautiful but extremely expensive, and after you've spent time on Rhodes and Symi I think the crowds might be overwhelming.

I'd love to hear your opinions of Rhodes & Symi after your trip!

Just to be clear: Yes, Santorini can be very expensive, but it doesn't have to be. There are lots double rooms available in May for under €30. It just depends on what you require and where you choose to stay. Not every hotel is a 5-Star Luxury Resort, and not every restaurant is overpriced.

If you have 4-5 days in Rhodes, you might plan a day trip to Kastellorizo. We've added it to our itinerary for next fall. There are some beautiful hotels with great reviews on TripAdvisor (if you want to stay overnight), and here's an excerpt from a TripAdvisor trip report that started us looking at this island:

"Today we took the Dodecanese Express to Kastellorizo. 2hours and 30 min. sailing but it was oh so worth it! Entering into the harbour with its pastel shaded houses was just amazing. We had a lovely walk to the castle, windmill, the town center of Chorafia and down to the sea again in Mandraki, on the other side. Here we went for a swim, so peacefull, and what a view! Back to the harbour we had enough time for eating ice-cream, having a drink and a second swim. Kastellorizo is lovely. There's a lot of renovation goïng on, and now day-trippers start to discover the island. Make sure you get there in a few years to come before it gets too touristy."