Help with 3 week itinerary based on earlier feedback

I'd recommend spending the entire month in Greece. Three nights in Santorini sounds good. And then I'd suggest 4 or 5 nights in Naxos. It's a great island with lots to see and do. Stay on St. George's Beach.

Then ferry to nearby Amorgos for 3 nights. It's a small, lightly touristed island. No crowds. There are two ports on Amorgos; I loved Katapola, and stayed at a wonderful pension called Porto Katapola, in a room with a large balcony overlooking the busy harbor. Great restaurants along the harbor and the fascinating Hozoviotissa monastery to visit.

Then ferry back to Naxos and onward to Paros ... and either stay on Paros or keep going to Antiparos, a tiny island just offshore. From Antiparos we took an all-day boat tour called Lazy Day with Captain Ben. He starts in Antiparos but also travels to Paros to pick up people, so you could enjoy this from either location. A delightful way to spend a day. Antiparos is a charming, quiet, uncrowded island with some great restaurants.

Then ferry or fly back to Athens and start your mainland adventure.

Regular travelers to Greece generally recommend you fly to your first island immediately on arrival in Athens. There are late flights to Santorini so you might want to see if you can make a connection on May 1.

I think you are short changing Naxos. Two nights is really only a day and a half. In my opinion 4 nights is the minimum you would want to stay in Naxos. At that you will only see a bit of the island. We always stay 7 to 10 days in Naxos and are still finding new things.
Naxos Mountains and Villages http://www.flickr.com/photos/stanbr54/sets/72157632110674306/
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

You might not need two nights in Delphi. We arrived in the late afternoon, visited the museum visited the lower site and enjoyed the village. Next morning we were up for opening of the main site and had it virtually to ourselves for two hours before the tour buses arrived. It took another hour before the crowds caught up to us and we left. This wold be a good time to head for Olympia. Thats a good 5 hour drive so you will be arriving early evening. Same strategy be at the opening first thing in the morning before crowds arrive.

You can probably do the site in 4 to 5 hours so you still have a good part of the day left. Now you can drive into the Peloponnese with Nafplio as your goal. Perhaps spend some time driving along the coast visiting Pylos area with its Venetian castles, the Mani is a very different place with its tower houses and mountain villages. You might want to visit Monemvassia and Mystras on the way to Nafplio. You can easily use a week in the Peloponnese.
Olympia Delphi Meteora https://www.flickr.com/photos/stanbr54/sets/72157645469717811/
Peloponnese Battle Castles https://www.flickr.com/photos/stanbr54/sets/72157645468134284/
Nafplio and Peloponnese http://www.flickr.com/photos/stanbr54/sets/72157632094108982/

As u know (if y have read my posts on other threads) -- I think NAXOS merits 4 days, especially in May. Santorini is only 12 miles long; Naxos is largest (AND most green, most fertile) Cyclades isle ... with Just 2 nights (1.5 days?), you won't get beyond its fab port town. You want "less touristy" spots -- yet Santorini is MOST touristy place in all Greece! (Even waiters aren't greek, they're Bulgarian!) By contrast, on Naxos drive 15 minutes inland in Early May & you can end up as we did, doing things like (1) sitting 40 minutes on a farmer's fence watching him shear sheep with a hand clipper, chatting merrilly despite no language in common (2) having coffee in tree-shaded square of hill village Filoti & kibitzing on domino game between local priest and mustachio'd retiree. (3)discovering an entire mountainside of blinding-white marble -- (4) then finding a marble-cutting plant with tiles sprinkled all around outside. BTW, u know those mysterious pre-Minoan marble statuettes that revolutionized the art of Picasso, Brancusi. Modigliani, Moore etc? NY's Met Museum devotes a whole room to display just 6 -- the tiny Naxian Museum has EIGHT CASES full... from 2" to 3 feet. So, Naxos is worth 4 nights -- & if you want there are day-excursions to Paros, Antiparos etc.

For those other extra days ... why rush away from Olympia ??? Even without a car I found my way south (2 busses & a taxi) on the West Coast. This map - http://euro-map.com/karty-grecii/peloponnes/podrobnaya-turisticheskaya-karta-peloponnesa.jpg (click & it gets huuuuge) shows the route. Stop at NESTOR'S CASTLE (remember him? from the Odyssey?) say hi to 2 Univ of Cincy archeologists who head this dig. Then mosey south to my Secret Eden, a favorite undiscovered gem (shhh! tell no one!) ... Just N. of Pylos is GIALOVA a tiny village 4 blocks long....Stay at ZOE's http://www.zoeresort.com/index.html -- despite the name, an adorable small family hotel. Rooms with canopied balcony overlook aquamarine sea; in May, you can walk 5 miles up this beach almost alone! Nearby • Navoroni bay, site of 2 famed sea victories, ancient modern • Vodokilia Beach one of worlds most stunning (and protected) beaches • wonderful wildllife sanctuary. •3-4 Castles Moving on, E of Pylos you can detour 15 miles to ANCIENT MESSINE, has 2nd longest wall in the WORLD (next to China's). Stunning! NO tourists! ... I URGE you to see this area NOW because it can't hold out long against Super-Luxe World ... one extra-elite hotel already at N. End of that beach. Heading east from there u can stop a few hours at MYSTRA, deserted wonder-town of Medieval buildings. You can do all that in 3-4 days... you'll probably never come this way again, and I sadly predict it will be changed in a few years. Go NOW. Naples & Amalfi easy to do another time, & no need to hurry; they're already totally touricized.

I'm surprised u haven't yet discovered highlights like above. Have u done all this planning without a guidebook?? Alas, the internet alone cannot provide the insight to make the best choices (Ive been to Greece 12x & STILL seek out new books. Browse your Portand Library & take home an armful. but if you want a single reference, I favor ROUGH GUIDE to GREECE. Not a big outlay; in fact Amazon offers used copies of 2014 edition which I like a bit better than the newest edition -- you're not using it for hotel & restaurant info, but for landmarks & culture, and those don't change much. & You don't have to take Big Fat Book Along. Just pull out vital sections (Athens, Cyclades, Pelops, Phrase list) & bind their "spines" w Duct tape and Voila! pocket guide-ettes!

Aha, friend Stanbr got there first with exact same advice -- and while I had to paint word-pictures, he could provide ACTUAL pix!

I want to add my voice to the chorus suggesting you stay at Naxos longer than 2 nights. We were there for four nights this past May and it really wasn’t long enough. Ideally, I would have stayed at least two more nights. Our party divided up for the first day and a half and when we looked at pictures we all saw what we had not seen! It really is a varied island and there is so much to explore.

Beth

I really appreciate all of this advice. we WILL add the days and stay in Greece! This forum has been so valuable and offers more than guide books can. keep it coming.