Creating a Greece Itinerary

You ask a lot of questions, but to give you the best answers, we need more info. Some key factors are:
(1) HOW MANY DAYS? (don't count arrival or departure days) and what day of week would you probably arrive? -- this affects your options for flights & sightseeing (2) WHERE FLYING FROM? You may think this doesn't matter, but it affects whether u could get flights that arrive by 9 or 10 AM... giving you the most options onward, and (3) Group make-up: singles? couples? 25 or 65? it makes a BIG difference -- both in $$ and energy level and interests. We know a lot but we aren't mind-readers, alas. LOL.

And NO -- there is no need for concern about the immigrant/refugee question impacting tourists in any way ... this challenge is dealt with by authorities, and anywhere near where you would be -- and BTW, the "unrest" is not in Greece, but a great distance away, fortunately. It would be like not coming to Wisconsin because there is a kerfuffle in New Orleans.

Here are some considerations:
SEQUENCE -- Unless you have quite a long holiday, you must plan time efficiently. Thus, it is most efficient to save Athens for last; you "gain" a half-day if immediately on arrival, you switch to a domestic flight to your farthest point (such as Santorini). Then after a few days, take a short ferry to Naxos (what IS it about Hydra??? All the Rick-ites list it!!), then fly/ferry back to Athens for final 2-3 days. A bonus of Naxos is that -- unlike many other isles -- it has 2 companies that run DAY excursions. Thus you could see Mykonos as a day trip. May's a good month for that because the sea is very smooth then. Ending in Athens u could do your foodie tour, night life etc ... by being in Greece for awhile you'll be much more savvy, more able to enjoy the busy vibe of a city.

COSTS -- "Expensive" (whether for nightlife or hotels) is such a relative word! It helps to know what spending bracket you are comfortable with, if you'd give the price range you'd prefer for a double room (in EUROS please -- here's a handy conversion website -- http://www.xe.com/currencyconverter/ ) You're lucky, right now 1 € = $1.095 -- best it's been for 12 years. Keep in mind that Athens & Santorini will be the most costly in May. At the latter, rooms with Caldera views at a pool hotel, can be very high in Oia; about 25% less in FIrostephani, and also in Athens. Naxos beachfront doubles can be as reasonable as €55-70. As for meals, in simple island tavernas, two can eat hearty dinners with a liter of wine for €25-30, unless they opt for the costlier fish dishes.

SIGHTSEEING -- When you ask "is Delphi worth it," it indicates you haven't yet done much research on Greek history, art, etc. Delphi is a sacred site of Ancient Greece, where the famous Oracle was ...a beautiful sight high in the mountains, but it means most to "Graecophiles." I think it would make your group experience so much more rewarding if you could take the coming months to read up a bit on Ancient culture/art/history of the World's First Democracy, and ALSo something about the inspiring struggle of Greeks in the 19th century to finally gain independence after centuries of conquest & oppression by others. Then some of the landmarks will mean a great deal, not just a building or a pile of stones. If this interests, I can suggest some rewarding guidebooks and websites, but won't list them here, this is too long already.

EYE CANDY --- Everybody already knows the Santorini views, they're all over calendars & travel posters, but here are a couple of tasty albums showing some Naxos Highlights, and Athens around the Acropolis:
TRIP AROUND NAXOS - http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
WEEK IN NAXOS JUNE 2014 - https://www.flickr.com/photos/stanbr54/sets/72157645113682278/
ATHENS ACROP. AREA - http://www.flickr.com/photos/stanbr54/sets/72157632121475515/

I hope this helps you gather your thoughts for your get-together.

Janet thank you yes it does help. We are a group of three couples all around 40. We will be on the ground for 12 nights. Arriving on a Sunday most likely in the morning and departing 12 nights later on a Friday.
In general I like to start my trips heavy on the sightseeing places (Athens) when my energy and excitement is boundless. And then end it on a more low key note when I am burned out on museums and exploring. I feel like I would rather end the trip relaxing in Santorini then heading back to Athens for an ambitious itinerary. As far as money goes, in general I try to target $100-$150 a night hotels and consider $200-$250 a splurge if I want to kick it up a notch for a couple nights. Can you find nice places in either Mykonos or Santorini for $200 a night? And then dining - I didn't want to be on an island where the only option for dinner is $150 tabs every night for a couple. When I think of nightlife - I would dislike a Miami kind of nightlife. Clubs with lines and noise and everyone dressed to the nines. I would enjoy Madrid nightlife - casual, tapas hopping, strolling and enter any place that looks good. Which is closer to the Mykonos vibe?
Lastly I wouldn't have even known about Naxos if not for this forum and it looks great. To RS credit, he's not ever steamed us wrong yet on small character towns so I tend to trust those recommendation but am totally willing to forgo it if Naxos has more appeal. Thanks for the links for pics. I am going to look at them now. Much appreciated.

For the Madrid ambience, Athens is what you should be looking at. Mykonos, hmm, hard to say -- the real night life starts so late, I've never been up to experience it. And I tend not to like what the cruise ships have done to places like Santorini & Mykonos... you'd be there in mid-week and sometimes 3 or 4 monster cruise ships come in, so that means 7 - 8,000 people at least clogging the streets, taking photos, buying jewelry etc.

As for "ambitious" sightseeing, that is not necessary in Athens ... you can limit your time to 2 days, and just see the basics. And if you stay on the South side of the Acropolis, where there's a wonderful pedestrian promenade that goes on for more than a mile, it's blessedly stress-free, car-free. You can walk through a forested glade to go see the Dora Stratou open-air dance theatre ... a stunning cavalcade of authentic dance & costume.

As for the Miami nightlife version --- nothing like that in Greece. In certain places & clubs that only Greeks go to, the younger crowd dresses up a lot, hi heels etc ... but everywhere else, casual. I already told you what the kind of dinner prices are like in Naxos ... they can be like that in Santorini if you don't restrict yourself to Oia ... which is where most of the luxe hotels and high-rollers are. One of my favorite restaurants for the sunset is in Fira, top floor terrace of Stani ... wonderful views... stop by early & reserve the best table ... and it's hard to spend more than 20E per. Not International cuisine, just good traditional Greek dishes.

About the sequence I suggested -- going to an island first does save backtracking, you can use up half a day going in to Athens (1 hour mininum to Syntagma), finding hotel, checking in, etc. -- and then you have to do it all over, at the end. But if your people are all coming from different places at different times, I guess you'd have to do it. And at least you have 12 days not 8.

If you do start with Athens, then in your place I'd fly to Santorini Next, then do Naxos last for the relaxing part -- simply because for me at least, Santorini or Mykonos aren't "low key", due to cruise crowds and package-tour throngs. I suppose if I booked some away-from-it-all spa, it would be quiet, but that's waaay beyond my budget, or even yours. Naxos by contrast is a large island, not overwhelmed by tourism, a nice buzz of nightlife in the port town, yet very serene in May. Inland a few miles from the beach are farms, vineyards, herds of sheep, dramatic mountains of marble, temple ruins, and sleepy hill villages where the local priest sits under the plantain tree in the square, playing dominoes with mustachio'd retirees. I remember one May morning when a friend and I sat in an olive grove for hours, sketching, the only sounds the clucks from a flock of turkeys wandering through, and the distant church-bell from a chapel on the mountain. Then we caught a bus back to our beach, went swimming, had a nap, walked to the port-side tavernas for dinner and some music.

We were in Greece about six weeks ago, found Delphi a magical place but we had the luxury of two nights and a full day there. It's a small town on a steep hillside with views over a valley full of olive trees to an inlet off the Gulf of Corinth. The main "sight" is the ruins of the Sanctuary of Apollo, which we found beautiful and compelling, with the accompanying museum. If you're not interested in classical Greek history, mythology, architecture etc. I wouldn't recommend Delphi. If you are, you will find plenty to see in and near Athens in the time you have. There are all-day tours from Athens to Delphi and back but it's a long ride each way with, I'd think, too little time to appreciate the destination. If you had a longer time, and a strong interest in the classical period, Delphi would be a good addition (as would Epidavros and Mycenae, closer to Athens).

Janet is a great source who helped us a lot (thanks Janet!). I agree with her about not letting "unrest" deter you. We found every Greek we met to be friendly, helpful, and appreciative. (Except the driver we inadvertently cut off in city traffic who was quite upset, with justification but maybe still overreacting.) Hospitality, "love of strangers," is hard-wired into their culture. We saw no refugees or anything that might have alarmed us (not that refugees would have). I wouldn't have wanted to visit Lesbos or Kos or some of the other eastern Aegean islands where people were landing, because those places were being overwhelmed, but we saw no evidence of the refugee crisis in Athens or the mainland, or Crete. Overall we found Greece quite inexpensive, especially meals, including Athens. Don't know about Mykonos or Santorini.

Have a great time.

Thanks Dick -- it's always rewarding to hear back from someone who found our tips useful.