Something must go! Turning Greek islands wishlist into itinerary

Your list is the opposite of Slow Adventure, which you acknowledge. With 12 days, you need to knock off TWO . First is Meteora. TOOO Far when mixed with all those islands (there IS a 1-day train trip there now, but such a "drive-by" rush! Only a hiking experience if you take 3 days). You are young. You will be back to Greece many times, if you go to the places you list you'll fall in Love with GReece as I did ... and return when you have more time. Don't ruin a good t rip by too much of a muchness. You can't pour a quart into a pint bottle. Also -- island-hopping is time-efficient only if you can Walk on water or have a Magic Carpet (and those phenomena are not around recently) ... so each change takes at least half a day. Some Analysis:

GOOD TOOL to compare SIFNOS/NAXOS re hiking = http://www.cycladen.be/IntroductionEng.htm- This Nutty Belgian has devoted his life to hiking Cyclades, rating the walks, AND describing step by step, WITH photos. These are 2 of his faves.

SIFNOS one of my favorite islands, but a particular challenge since it's in Western Cyclades chain, look at a map (I hope you have, not trying to do this all on your smart-phone). once you get there, hard to "hop" to Central Cyclades... only links are Santorini & Paros and not every day.

SANTORINI -- guess what? those beautiful white buildings with blue shutters are not an invention Santorini! The exact same houses are on TWENTY-PLUS other Cycladic Islands. In fact, they're at their best in the hill towns of Sifnos. Why don't people know this? Because calendars and travel agencies and cruise lines Only promote Santorini and Mykonos, the "cliche twins" of US tourism. So just go for ONE day/night to see the Famous Caldera View ... and use Santorini as a "Connector island"

OTHER PLACES --
Western CRETE is splendid, I've been there at least 5x, 5-6 days per time, have only scratched surface. I tend to favor Imbros Gorge because in may only a very few other hikers (in May we only saw a dozen people in 4 hours), Samaria may be a long unending line, you'll look at someone's back the whole way, but that's your choice. Aktrotiri is a great place to hike near chania ... Also all the little hill towns just inland from N. Coast. AND the cliffwallk from Loutro to Hora Sfakion. so many choices. BTW, you can't really "base" in 4-5 days, too much backtracking. 2 days Chania then move on, end up in Heraklion for next "hop."

NAXOS is my overall favorite... have been there 13 times, make new discoveries each time; marble mountains! ruined statues in Orchards. An Apollo temple rediscovered, tiny churches in the hills, Mt. Zas, vineyards, farms, lovely villages, gorgeous beaches. Stay in St. George beach adjacent to town - bus or ATV to outer beaches.

Possible Scenarios
FLY Day 1 to CHANIA Crete(5 nites) - Ferry to SANTORINI (1 night) - Ferry to NAXOS (5nites) FLY/Ferry to ATHENS (2 nights)
FLY to CHANIA CRETE (5 nites) - Ferry to SANTORINI (1-2 nights) Ferry to SiFNos (4-5 nights), Ferry to ATHENS (2 nights).

I Put in ATHENS -- u really need at least 1.5 days to glimpse the world-famous landmarks -- stay near Acropolis (I like the area S of it, near Acrop. Museum... no traffic, lovely pedestrian promenade. This booking dot com link http://tinyurl.com/heq6edp lists hotels by how close to Acropolis -- limit your choice to those 1.2 km to Acropolis or closer.

Janet is probably the most informed person on Greece and her thoughts are pretty much right on.

I'll just add a few tweaks. I have never been to Sifnos so can't comment but Naxis does tick every one of your wants. It has a lovely main town with waterfront promenade and old market area with crazy back alleys and topped with a Venetian era Kastro. It has great beaches and mountain villages. Lots of decent hikes too.
You could easily spend your whole vacation on Naxos and will not be bored for a second. We have been to Naxos 14 times and will spend two weeks there again this summer. We are still finding things we have missed on previous trips.
In May Naxos will have full tourist infrastructure up and running and there will be enough people there for it to have a nice buzz but not crowds.
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/

You could also spend your whole time in Western Crete. Chania is a beautiful city with its Venetian era harbour and old town. You probably need two nights there just to cover this area.
Chania http://www.flickr.com/photos/stanbr54/sets/72157632117917828/
Chania May 2016 https://www.flickr.com/photos/stanbr54/albums/72157671465596275

Following Janets plan this leaves you about three days. If the Samaria Gorge is a must see then I would suggest you drop off your luggage at the KTEL bus station and hike the Gorge and catch the ferry to Sougia. Sougia is a delightful little village on the Lybian Sea. This area is great for hiking but after the gorge you will probably just want to hang out on the beach. Sougia also has three great tavernas. There are 7 in total but we have not been able to get past the top three.
Ferry trip Libyan Sea https://www.flickr.com/photos/stanbr54/sets/72157653434073393

Sougia https://www.flickr.com/photos/stanbr54/sets/72157653311291723

Stay two nights then take the bus back to Chania collect your luggage and take the bus to Heraklion for your last night. While Heraklion is a busy dusty noisy city, the central area and Venetian harbour will give you a pleasant place to visit. You do have to go to Heraklion to catch the morning ferry for Santoirni
Heraklion https://www.flickr.com/photos/stanbr54/sets/72157655935354556

Assuming you fly into Chania you can do this whole trip by inexpensive KTEL buses no need to rent a car..

If the Gorge isn't a top priority then you might consider visiting Ancient Aptera, and taking the day boat excursion to Balos and Gramovossa. You get two nice beaches and a pirate fortress. You can also start your trip to Heraklion with a stop in Rethymnon to visit the Venetian Fortezza. Again everything but Aptera can be done with local bus.
Western Crete http://www.flickr.com/photos/stanbr54/sets/72157632115757899/

Aptera images 38-62 Balos Gramovossa images 79-106
Rethymnon https://www.flickr.com/photos/stanbr54/sets/72157654700502270

Even though Santorini is overpriced and overhyped I certainly believe it is worth a night just to experience that view. This is where you should consider blowing the budget and get a caldera view hotel. You will remember the at view for the rest of your lives.

Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

Stanbr and Janet, thank you SO much for your thoughtful advice, it is truly so helpful. My itinerary is now, dare I say it, looking closer to sane.

I had remembered seeing some specific advice from Janet about where to stay in Naxos - I think the gist was to stay in town but where it's easily bus-able to beaches. I haven't been able to re-find that forum posting, and would love to hear that again/be directed to where it's posted.

Thank you again!

Where to stay in Naxos is actually right in Janets post above. St George beach. Its part of Naxos town but is about a 10 minute stroll into the main waterfront promenade. So actually you get a beach vacation with all the activities of town.
Naxos town is the hub of transportation for the bus system so you can visit the whole island from there and of course teh ferry port is there as well.
I posted images of Naxos town in my earlier repy. I think there are images of St George beach as well but here are more extensive images of the beach area.
St George Beach Hotels Naxos http://www.flickr.com/photos/stanbr54/sets/72157632162394787/
St George Beach Naxos http://www.flickr.com/photos/stanbr54/sets/72157632113170279/

Hi Kate!
By now you have figured out that Stanbr & I are a "tag team" (as well as friends), separated by a continent. What I omit, he'll fill in from Vancouver, a few hours later. You ARE late in getting reservations, in all 3 places ... Santorini will be the most challenging, since May-June is "Bridezilla Season"!! for all 3, I suggest using booking.com for sorting your choices (I already gave you an Athens special-sorting link). The key of course is location location location -- and booking.com can shortcut this search process. You put in the destination, your dates, and when a list pops up, on the first choice (even tho u don't want it), click on its google map and enlarge; this shows you ALL the booking.com choices as little balloons -- RED for fully booked, BLUE for rooms still available, WIT $$ prices. U can use this map to determine posssibles ... if there's a RED Baloon you still long for, write the hotel direct, they may have rooms they didn't allot to an agency ... not likely but maybe. BTW, so close to your dates, fewer rooms will be offered as no-penalty cancels. As Stanbr advises, a Rating level of 7.8- 8 up usually assures you of a pretty good experience.

NAXOS -- In May we usually advise staying at St. George (Ag. Giorgios) beach directly adjacent to town (this good SKYMAP shows exactly http://www.skymap.gr/apps/site/viewmap/?mapid=29&cid=305) Some places that are closest to, or ON the beach include HOtel Asteria, Studios Thomais, Studios Kalergis, Studios Diogenes, Villa Naxia, Hotel Kymata, Sun Beach, Galazia Studios -- many who claim to be near are NOT; always check map.

SANTORINI -- Here, I usually recommend a Caldera-view room (if possible) in FIROSTEPHANI, a location "sweet spot" which has a lot of caldera rim hotels... is at the north edge of FiRA town (walkable to shops, museum, cafes, nightlife) , but is visited by NO package-trip throngs or cruise crowds, yet has a very handy bus stop enabling you to get to OIA (go EARLY -- 8 AM if possible, to enjoy crowd-free lanes for a couple of hours before the thousands flood in from ships & tour busses). As above, put in "Firostephani" in search slot, and look for "blue balloons" near the rim path... good luck! you'll need it! Probably no pools except at stratospheric prices. In the OIA area, Stanbr has found a less-known venue, a little village adjoining OIA, where NIKOS VILLAS is mentioned. For rimside views, put in OIA and open up your wallet!

CHANIA -- You didn't say whether you'd obtained lodgings there yet. Same advice applies -- put in "Chania" and dates, and look for the Blue Balloons -- the area we Chania-fans like best is On or just off Theotokopoulu Street, just 100-200 yards west of the harbor ... near the action of harbor but serene at night, charming, some sea views -- the street has Dozens of modest places, many renovated from Venetian town houses. Places I know personally include Casa di Pietra, Hera Studios (which is also offered as an Airbnb), Hotel Palazzo (under new mgt & upscaled a bit, now called "boutique"), Pension Nora, others are Iason Studios, ANemeones. If you want to stay about .5 Km WEST of Old Town, on the Chania beachfront, there are a ton of apts & studios u can see on this map -- https://www.hotelscombined.com/Place/Chania_1.htm?mapState=expanded%3D1 -- you'd be mainly among Europeans & Greeks there. BTW, this little town beach in May can be an unexpected treat... lots of locals. I remember a late afternoon, when dads would come zooming up on scooters w. kids in back, tossing them in the water for play before dinner. We had just stopped by for a dip, but ending up getting pizza from across the street and staying til twilight.

You two are amazing! So generous to do this. Can't believe I hunted all over the forums for what was in this response - please allow me to blame planning-brain. We're in endless fog and rain all weekend, so I will be hunkered down trying to book lodging. Thank you again. If you're ever visiting coastal Maine please reach out.