Greek islands bucket list

Mykonos & Santorini are two of the most heavily touristed islands in Greece. Also tend to be a lot more expensive for everything. There are numerous other islands that may give you a more "Greek" experience if you are looking for that. Islands like Sifnos, Milos, Naxos, Amorgos, Lemnos, Serifos, Folengandros, Skyros and several others tend to be more family-friendly with more tradition and local flavor.

Since you'll be on the islands late Sept. & early Oct. you'll be out of the high season so Mykonos & Santorini will not be as crowded but still crowded, expecially with the cruise ship crowds. One thing to remember about Santorini is that many of the villages were destroyed by an earthquake in the 1950s so what you will be seeing are not centuries-old houses but reconstructed versions. Still impression however with spectacular views.

So many factors involved with deciding on what island(s) to go to and what your interests and desires are.

Just a bit more clarification please. Will you dates include travel days or will you actually be in Greece from the 26th to the 4th. The difference is between 9 days and 7 days.
Also do you have flight times for your transatlantic. If so you might consider catching a connector flight to Santorini immediately. You will need two hours. Go to Aegeans web site and see if there are flights available. Athens is a very busy hectic city and not the best place to get over jet lag.

Santorini is absolutely spectacular and a must see destination. It will be expensive but be sure to get a hotel with a caldera view. Be sure its a Caldera view there are hotels with sea view and that simply isn't as magnificent as a Caldera view. You should be looking for a hotel in Fira the busy capital or Firestofani part of Fira with the same views just a bit less expensive and quieter. Or you could go to the beautiful village of Oia on the tip of the island. You can't find a better place to get over jet lag.

With such a short time frame you can probably only have two or possibly three nights on Santorini.
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

You will connect with your second island by ferry. Frankly Mykonos is a nice island with typical white and blue buildings but it is heavily promoted which means it is expensive but it is no better than several other islands easily reached from Santorini.

I am going to suggest you consider Naxos. Its a two hour ferry ride. It has a lovely main town with a maze of tiny back alleys all topped by a Venetian era Kastro. It has some antiquities, mountain villages and, some of the best beaches in Greece. All of this at probably a third of the price of Santoirni or Mykonos. It makes a perfect companion island for Santorini.
Naxos deserves 3 to 4 days and you can't see everything in that short time frame. Please tell me you have 9 days.

Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

If you only have 7 days then frankly you don't have enough time to do a second island because Athens also deserves a minimum of 2 to 4 days.

Athens http://www.flickr.com/photos/stanbr54/sets/72157632121475515/

Whatever you do, you have to be back in Athens at least the day before your return flight. Stuff can happen and you would be in a pickle if you are stuck on an island trying to catch your return flight. I have seen that happen.

Hope this gives you something to think about.

Thank you Stanbr, for saving me effort. You said EXACTLY what was in my mind, but said it so much more lyrically. Elaine, listen to The Man! He knows both islands SO well, he wasn't born yesterday, and he's taken wonderful photos of both ... I never even bother to post my pix, I just use his!!!

Santorini doesn't have to be expensive. Yes, there are plenty of rooms available that are sky-high but there are lots of hotels offering single rooms that are really no more expensive than a Motel 6 here in the States. It really just depends on your location and the sort of hotel you're used to. All you have to do is use the filter system at www.booking.com and search for what you want at the price you want to pay in the part of the island you prefer.

Santorini is beautiful!!. While there you might want to do a day trip to Oia. If you do go to Mykonos, a short day trip to Delos might be worthwhile to you. Google Oia and Delos and see what you think.

Hey Lee good to find you here. While I quite agree Santorini does have reasonably priced hotels, after trying that option we missed the views so much that we checked out of our cheap hotel and paid three times as much for a hotel with a caldera view.For a first time visitor I believe that having that caldera view is worth stretching ones budget. Those rooms are expensive but in my mind are worth it for the view.

Hi Stanbr. You'll get no argument from me about the desirability of staying on the cliff! Unfortunately not everyone can afford it these days, myself included. It's a far cry from my first trip when I rented a small house on the cliff in Oia for $175/month!!!

Hey Lee you are showing our our ages.

What do you mean "our ages"?? I was only a very precocious 5 when I rented that house! :-p

When you comment that these islands are more expensive, does this relate primarily to lodging or food / beverage as well? Are we talking 4 more Euro for a nice lunch or 15?

We are talking hotels with Caldera view being at a minimum twice as expensive as hotels at the Santorini beaches or on the east side of the island.
Food and drink is also more expensive if you are in a taverna with Caldera view. I recall paying more for two ouzos and a tiny bowl of chips at a Caldera view taverna than our whole dinner meal on Naxos. To economize one can look for a Gyros and beer.