First time, 4 weeks, Family of 5

Santorini is popular for a reason: it is drop dead gorgeous. A room with a view of the caldera should be on everyone's bucket list.

Cala,

Thanks. Thats what I thought...
Jess

For Crete you'll need a rental car. It's a huge island. If you live outside the EU be sure to bring an International Driving Permit.

I agree. Don't skip Santorini because of its reputation. There's plenty to see and do there including hiking, museums, wine tasting, 2 interesting archaeological sites and cliff jumping. There's a 2-hour ferry from Heraklion, Crete to Santorini. It leaves at 9am.

Cliff Jumping: https://tinyurl.com/y75knz7n and https://tinyurl.com/yaq466ns

Archaeological Sites: https://tinyurl.com/y8ofdxoj and https://tinyurl.com/y92l3aj7

This sounds like an amazing family experience. Where are you coming from? When will you be arriving in Athens? Experienced visitors choose to catch a connecting flight to the first Island immediately on arrival in Athens. That way they can get over jet lag on an island rather than the hustle and bustle of Athens. This saves the commute into Athens and back to the airport airport twice. Visit Athens once at the end of the trip.

So if it were me I would choose to fly to Crete on the day of arrival. Chania is probably the prettiest city in Greece (along with Nafplio) Its old town and Venetian harbour are as if you stepped back into time.
Chania http://www.flickr.com/photos/stanbr54/sets/72157632117917828/
Chania May 2016 https://www.flickr.com/photos/stanbr54/albums/72157671465596275

Chania is going to take a couple of days to visit the old town and Venetian harbour.
It is also perfect location for day trips to nearby locations such as Ancient Aptera (still an active dig site) and Balos lagoon. There is an excursion boat from Kissamos to Balos and Grasmovosa. This excursion gives you two great beaches plus a 14th century pirate fortress. You can book an organized tour from any travel agent or just hop the KTEL public bus which has morning run to get to the excursion on time.

Chania is also the kick off point for the Samaria Gorge excursion. Again this can be done by local bus or an excursion. This is a full day hike so you will need to schedule a down day after that hike.
You can also do a day trip to Rethymnon to visit the Fortezza.

Western Crete http://www.flickr.com/photos/stanbr54/sets/72157632115757899/

Aptera images 38-62 Balos Gramovossa images 79-106

I am going to make a radical suggestion now. Consider dropping the Samaria Gorge plan from Chania. Instead take the local bus to Paleochora. Its a lovely town on the south coast of the Libyan Sea. It has beaches, a fortress ruin, a day boat to the pink sand Elafonissi beach and every evening the centertown roads are closed and the area is transformed into street tavernas. There is also a daily bus from Paleochora to the top of the Samaria Gorge so you can do the trip from Paleochora. At the end of the Samaria gorge you have to take a ferry back to your bus to Chania but if you start the trip from Paleochora while everyone else has a two hour bus ride through the mountains you will be sitting at a taverna enjoying the sunset.

The coastal ferry trip is also an unforgettable experience. You can take the ferry to the next village Sougia ( which in fact is our preferred place to stay) Its much smaller than Paleochora, very laid back but has at least three great tavernas, a large beach and hiking opportunities. At the far end of the beach you can hike to Lissos Plateau where there are extensive ancient and Roman ruins. There is also a water taxi. At the other end of the beach there are rock formations where people regularly do cliff jumping.
Sougia https://www.flickr.com/photos/stanbr54/sets/72157653311291723

From Sougia the ferry goes to Agia Roumeli where the Samaria Gorge hike terminates. My knee cant take the full hike but we did walk from the bottom up to the last rest stop of the Gorge hike at Christos.
Samaria Gorge hike the easy way. https://www.flickr.com/photos/stanbr54/albums/72157670610409530
From Agia Roumelli a second ferry takes you to the charming village of Loutro and then on to the end of the trip at Chora Sfakion. You can easily spend a week in this part of Crete.
Ferry trip Libyan Sea https://www.flickr.com/photos/stanbr54/sets/72157653434073393
Crete Libyan Sea villages https://www.flickr.com/photos/stanbr54/sets/72157645487373222/

I have run out of room on this post. Later i will discuss historical sites on Crete as well as the Peloponnese and Delphi.

Definitely Athens at the end so you don't have to worry that weird weather will cancel your flight or ferry back to the city and cause you to miss your flight home.

I'll just add one practical consideration: I would leave Athens for the end, not for the beginning.

There may be rough weather conditions like strong winds at any time of year that might lead to canceled ferry boat connections, so it's good to have a day or two of buffer zone before your return flight.

[Editing to add @acraven: Your post wasn't there just a moment ago when I wrote this, but obviously... great minds, and all that... :-) ]

.

In terms of hiking, there are great possibilities on many islands. Look for the ancient donkey trails. Many of them are great for hiking. It may be difficult to get reliable maps for some islands, but if you are experienced hikers, you will find your way around.

... there will be "nothing" to do but the beach

If you ask the average tourist, they'll know only the beaches. But as soon as you leave the coastline and go farther inland, many islands have great opportunities, and you will immediately be away from all the touristy crowds. Here are some that we have done: beautiful forest hikes on Skopelos, hikes to remote monasteries and chapels on Paros, crater hike on Nisyros, up the Profitis Elias mountain on... -- I can't remember, every island seems to have a Profitis Elias!

If you are really ambitious, part of the European long distance path E4 goes across Crete.

I love these suggestions. I loved Greece and now am adding Crete to that wish list!)
Just be sure that your hotel in Athens has air conditioning. The heat can be brutal!

I love these suggestions. I loved Greece and now am adding Crete to that wish list!)
I found Delphi to be magical, so it's worth a day trip or a lengthy stop in my opinion.
Just be sure that your hotel in Athens has air conditioning. The heat can be brutal!

Great opportunity to see and do a lot. I agree with others that it would be better to fly straight to Crete on your arrival day, if you can schedule it with enough margin to accommodate a delayed flight into Athens, and visit Athens at the end instead of the beginning. We spent three full days in Athens and could have used a day or two more. While it's a big city, we didn't find it especially stressful or unpleasant compared to others like Paris, London, New York, or what have you.

I haven't been to western Crete but Stan certainly has some great ideas there, and I've heard nothing but good things about Chania. But you also won't want to miss the Knossos site and the archeological museum in Heraklion. You might consider flying into Chania and out of Heraklion (perhaps a ferry to another island given all the time you have for this trip).

Nafplion and Delphi are definitely worth visiting. I'd suggest an overnight in Delphi so you can visit the ruins and museum before and/or after the big bus tours that come up from Athens. The early and late views from Delphi down to the Gulf of Corinth are wonderful. The town has lots of accommodations and eating choices. I'd suggest several nights in Nafplion so you can see the city plus Mycenae, Epidavros, Tyrins, and/or Nemea.

Rick Steves' guide to Greece doesn't cover any islands except Hydra, but it's very good for Athens and the Peloponnesus. You'll find lots of ideas there, as well as in the guidebooks you're already using for research.

Wow, thank you all so much. I ran out to the book store and came back to so many great ideas.

We are coming from Denver..

Lee - thanks for the reminder about the international driver's license. I drove in France last year where, after researching, found one was not required (but recommended). We're definitely planning to rent a car for Crete and the Nafplio area

Stan - this is exactly the kind of info. I am seeking. I was planning to spend time in a few places on Crete not just Chania) so moving to a town on the south side and approaching Samaria from there sounds awesome.
How much time would you recommend on Crete? I was thinking 7-10 days?

W.R.T. Athens, my thought was that after travelling for nearly 2 days to get to Athens, the thought of getting on another mode of transport to go somewhere else just might kill us (I jest, but we drive to Denver, fly to Brussels, and then on to Athens). So if we went to Crete first, would you suggest we also do the Peloponnese region at the end, or start in Nafplio, then head to Crete, then do Athens last....

Thanks again so very much,
Jess

Yes, sometimes it’s possible to rent a car, ATV or scooter just by showing your passport and a current drivers license. No problem. Some rental offices don't care.
BUT....................
If you get in an accident and don’t have the IDP you'll be in serious trouble with the Greek Police. Greek Law requires it and if you can't produce it you could possibly be detained until you come up with the cash to pay for any and all damages to the vehicles involved regardless of whose fault it is and whether or not the damages were pre-existing (especially if the other car belongs to a local seizing the opportunity to play the system!)
AND...................
Your insurance, including what your credit card supposedly provides, will be invalidated because technically you will have been driving illegally.
And in that regard I also encourage you to take out the local insurance offered when you pick up the car, as much coverage as you can get. Don't rely on the automatic insurance your credit card claims to provide you. You'll be in a foreign country and there won't be a claims adjuster handy.
Just as important: Don't take "No Problem" as a substitute for indicating on the rental acceptance form every little scratch, dent, tear, stain, crack and missing part on the vehicle, inside, outside and underneath the car. Take photos to back up your inspection. If the rental agent resists signing off on all that you've indicated walk away and find another agency.

If you can, try to find a flight out to Crete about 2 hours after your arrival in Athens. It's much much nicer to wake up your first morning in Greece on the beach somewhere as pleasant as Chania, instead of in Athens fighting traffic, crowds, city heat and noise while you get over your jet lag.

Driver's license: Be aware that this is true in both directions though. The IDP is completely worthless without your national license. So don't ever come up with the idea "I've got the international license, I can leave my national one at home".

I have been busy packing our house and have not had time to get back to you Jess. Our trips to Greece are from the west coast so even further than Denver so I do understand your concern with having to grit out another few hours to get to your island. Believe me we have done it both ways and waking up on an island the next day is way preferable than experiencing Athens Jet lagged.

I think you should consider 10 days to two weeks for Crete. Once you finish the Libyan Sea portion of the trip then I would suggest you take the bus from Chora Sfakion and head back North to Rethymnon then on to Heraklion. Heraklion is a noisy busy hot city but it too has a Venetian harbour and a very nice old city center. It also has Knossos and the archaeological museum. If you rent a car and head south from this area you will find Phastos another excellent Minoen site but the big bonus is Gortyz, It was the Roman capital and the city is essentially buried in an olive grove. Bring lots of water and wander in the groves. You will find streets, the forum, Governors Pratoreum, baths and columns lying everywhere. Its like you have discovered your very own archeological site.
Images of Crete historical sites including Gortyz are here.
https://www.flickr.com/photos/stanbr54/albums/72157691001013665
Knossos and Phastos
Crete Archeological sites https://www.flickr.com/photos/stanbr54/sets/72157645085297380/

And I certainly would use at least a week to drive through the Peloponnese. Naphlio is a lovely seaside town with two Venetian castles, a marble paved central square where kids of all ages come out to play every evening and a charming old town area. It is also a perfect location for day trips to nearby ancient sites. Further away be sure to find Mystras the last Byzantine city quite intact and then give the kids the highlight of the trip and stay in Monemvassia. Its a 14th century fortified town. Hotels are period rooms scattered around the city. You just have to play pirate at Monemvassia. If you have time continue east and go on a castle quest. This area has lots of Venetian era castles.
More images
Peloponnese Battle Castles https://www.flickr.com/photos/stanbr54/sets/72157645468134284/
Nafplio and Peloponnese http://www.flickr.com/photos/stanbr54/sets/72157632094108982/

And Delphi is probably one of the best historical sites in Greece.
Olympia Delphi Meteora https://www.flickr.com/photos/stanbr54/sets/72157645469717811/

Thanks Lee - Ive got the license on my "to do" list

Stan - thanks again. Im filing your info. away for when I get into detailed planning.

So far, here's what Im thinking: (In the list below, I still have 1 day to add somewhere if I stay in the below places for "4". Alternately, if I stayed for 3 days in the places Im debating 3 v. 4, plus add that unaccounted day, that allows for 4 more days somewhere additional, or spread around these). We will be in Greece for 27 full days:

Fly to Crete upon arrival in Athens. Then:

Crete - 9 days (divided between Chania, south coast, and east end, maybe three days in each)
Santorini - 2 full days (2 nights)
Amorgos - 3-4 days
Naxos - 3-4 days
Nafplio - 3-4 days
Athens - 2 days

"Additional" Im considering are Tinos and Andros... This would be our final island before heading back to the mainland. Im also thinking of taking out Naxos and putting in Tinos+Andros

I would love opinions :)

Jess

Honestly, I truly believe you're spreading yourselves too thin. First-timers seldom realize how much time is lost making the transition from one island to the next. It's not just the time the ferry takes. It includes packing, checking out of your hotel, making your way to the ferry port, waiting for the ferry, ferrying from one island to the next, making your way from the new port to the next hotel and checking in. You will repeat this every time you change islands. Some ferries aren't offered every day or depart at odd hours, so you have to plan accordingly. Depending on where you stay extra-late or early-morning arrivals might mean no check-in for hours, so in some cases you might need to find a hotel with a 24-hour reception desk. We take that for granted here in the USA but I promise you that's not always the case in Greece. Also, be sure to plot your course so you aren't backtracking. That's one of the biggest mistakes often made by Greece newbies wanting to island hop. This ferry route map link will come in handy: http://ferries-turkey.com/images/pics-maps/route-maps/800/ferry-network-800.png

Ferry schedules: www.gtp.gr

Thanks Lee, Im wondering about that for sure. I plan to delve more into transportation tomorrow. One thought is that our final island will be one from which we can fly to Athens. A lot to think about. In this map it looks like the islands I am considering fall more or less in a straight line and the line indicates more frequent ferries:

http://www.greeceathensaegeaninfo.com/ferry-info-greece/greek-islands-ferry-chart.htm

Ok it seems other than Nafplio the Pelop[oneese is not in your plans. Thats OK. However you are now adding so many additional options that you are creating a totally unwieldy plan. Rather than repeat what Lee said which is totally accurate let me tell you about the occasion we realized that every island hop eats up virtually a whole day. We were going from Paros to Naxos. That is a one hour ferry hop. Easy right. Well we had to check out of our hotel in Paros by 10 then hang around Paros town for 3 hours dragging our luggage around waiting for the ferry. Its a one hour hop however by the time we got to Naxos got to our hotel and were on the beach it was 3 in the afternoon. Every time you make a hop you are going to lose a minimum of a half day from your vacation just hanging around .

You have lots of time, thats great but if you make all the hops you are now suggesting at the end you will do a trip report saying we wasted a whole bunch of time waiting for ferries.
Honestly Greece is about minimizing hops and really enjoying less places more fully,

We visit Greece almost every year and from my pictures you can see we have been to most of the popular islands and with a full 35 days we only did East Crete, Santorini, Naxos and Athens Honestly even after 14 visits to Greece we easily could have added an an additional week to that trip and not seen everything there is to see on those islands.

I totally agree Santorini is a must see for a first time visitor. It is absolutely spectacular. So a Crete Santorini Naxos Mainland stay isn't a bad plan. I didn't suggest Naxos because much as I love it you were already planning to do too much. Something needs to be cut.
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

However Crete for 9 days plus Santorini for 2 to 3 days plus Naxos for 4 days to a week plus a couple of days in Nafplio and ending in Athens is doable but you would probably be better off adding to Crete, and dropping one of Naxos or Nafplio. All are excellent choices but probably one of them has to be dropped.

Just for fun here are images of Naxos. If you go there I predict you will rate it as the place you loved the most at the end of your holiday.
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/

Thank you both!

For context, we stayed 2-5 days everywhere on our 5 week trip last year and it was absolutely awesome. We visited Paris, Loire, Dordogne, Carcassonne, Provence, Cassis, Cinque Terre, Florence, Rome and Amsterdam. That list looks crazy, but sure enough, every time it was the day to leave a place, we were ready for the next adventure. And we never felt rushed and we spent a lot of time with/in all of the important places, as well as had plenty of down time (although Paris and Amsterdam were repeat visits)

In re-thinking, Nafplio and sites around it, and of the islands, I feel strongly about Amorgos. I know its the most out of the way and will suck up time in travel, but I'd hate to give that one up.

This is hard! :p

Currently Im working on selecting among:
Crete
Santorini
Amorgos
Naxos --> this is at the bottom currently = most likely to be cut
Nafplio
Athens - I know it should get due time, but we will spend 1 day here (2 nights) to see the Acropolis and anything else. Its just not our priority this time

(Im also realizing this is hard to do without a RS guidebook. I so prefer his to these others Im using, which Im finding not very helpful (Lonely Planet and Rough)

Thanks again for the heads-ups, and wonderful pictures,
Jess

Over the years we have seen a few people who just love to travel fast long and hard. Even though forum regulars have suggested that Greece should be experienced slowly and in depth, some people have a different style of travel. And that's OK. Virtually aver time those people come back and reported that they had a great time, saw everything they wanted to and are planning a return trip. What works for you is what is important.

By the way I understand Rick has visited just a couple of islands and might not have valuable info on the ones you are interested in. There is a Greece web presence called Matt Barrett. Its a pretty good place to get info during research time.

Stan - I know! (about RS not covering the islands). Thats what I mean - Im missing his guidance.

Im currently plotting out my days to see how much time I think Ill want in each so I know how many places are reasonable, and then Ill whittle. I have a fairly good idea for Crete, and so far it puts me at 9-10 nights. This may seem very fast, but I think I will focus on Chania-Paleochora-Amari Valley-Herak region - with Herak getting no time except the final night - and leave out the east side. I think Im looking for a flavor sampling and not necessarily a detailed excavation. So 1-2 ruins, not every one, same for beaches, etc.

I have found your posts on TripAdvisor about car-ferries along the Libyan coast. That was useful :)

Onward...

Here's the main Matt Barrett website FYI. There's more info about all things Greece travel than you'd ever want to know.

Apologies to Stan for calling him Alan above -- Alan from Brighton is another frequent poster with lots of Greece knowledge -- like Stan. I've corrected with an edit.

I guess I agree with others that your latest itinerary is too busy, keep in mind that travel between islands is necessarily lengthy unless you have your own yacht. (If so, I'll be glad to come along.) Also I think one full day doesn't do Athens justice, I'd suggest two or three, preferably at the end of the trip to reduce risk of missing the flight home.

Jessica,

Your plan to concentrate most of your time in Crete in the West is a good one, even though you will be missing out most of the big archeological sites. Knossos can be done in a morning if you are flying or ferrying out of Heraklio, but the newly(ish) renovated museum in Heraklion is marvellous too. Just 1 day & night there could be enough. Stanb has given you great ideas for the South-Western coast, if you don't want to spend more than a couple of days there I'd suggest Hora Sfakia & the ferry to Loutro at least. You can also visit the lovely beach of Frangokastello with its fort from there. & how about walking Imbros gorge, really easy from Sfakia, much shorter than Samaria, but also beautiful scenery, fewer people & you wouldn't need to schedule a day off afterwards for the stiff legs! & it's a scenic drive past the White Mountains back to Chania (via Vrysses).
I'd prefer to stay in Hora Sfakia or Sougia than Paleochora, they are smaller & have more atmosphere to me, but it's a personal choice, Paleochora is larger, with a big beach, lots of restaurants & bars & lots of people holiday there year after year.

After a few days in Chania itself, I'd also suggest either a few days, or at least a car ride day out from Chania, around the villages of Apokoronas - just East of Chania, this area is very traditional, with olive & orange groves & tiny quiet hamlets. At the beach level are Kalyves & Almyrida, both have lovely soft sandy beaches, if you stay in this area for a few nights you could go to the tiny bay of Koutalas near Kokkino Horio where it's popular to climb up the rocks (on the goat tracks!) & jump off into the clear bright water. Inland you get to many little villages in the foothills of the White Mountains & easy access to ancient Aptera as recommended by Stanbr. The traditional food is superb in this region, very natural, often organic, straight off the farm seasonal stuff.

Hi All,

Ok, my husband and I finally had 5 minutes to talk last night - and by that I mean he watched the RS episode on the Peloponnese ;) - and here is my revised schedule, with some notes (and maybe a question or two). I think you will approve (and yes Stan, it looks almost exactly like what you recommended from the get-go. I had to get to that understanding ;)

June
Peloponnese - 7 full days
19 - Arrive Athens 4p. Rent car at airport. Drive to Nafplio. (Can't fly to Crete. Flights to Crete are at 5p or 10 p. 1 hour to change planes stresses me out - even with no checked luggage, and there's no way Im losing those 6 hours in an airport)
20-27 - Peloponnese Peninsula. (Sleep in Athens airport hotel the 27th, arriving there late - just to return car and sleep - after our last full day in the PP [sleeping in Monemvasia the 26th, driving to Nafplio midday for afternoon walk and early dinner, then depart for airport at ~7p)

Crete: 10 days
June 27 - Arrive Chania 9a
July 7 - Ferry to Santorini 9 a

Santorini: 2 ½ days
7-10

Naxos: 4 days
10-14 - Depart/FLY to Athens on the 14th

Athens: 1 ½ days
14-16 - Arrive afternoon of the 14th, Depart morning of 16th. "Just" a day for the Acropolis

Question: Im sure I will have more (and for those I will start another thread ;) but for now, Im considering dropping Athens and just planning to arrive the day before my flight, rather than the day-before-the-day-before. Im wondering whether forging into the city is the best use of time if we are not going to give it more attention on this trip, and if perhaps an additional day somewhere else would make the trip more relaxed overall.

Thank you all for giving me the gift of your time and experience. I am feeling very grateful on this first morning of 2018. Here's to a peace-full New Year

Jessica

Looks good. Much more realistic. I recommend you take one more day in Athens so you have time to visit the new Acropolis Museum and the National Archaeological Museum. Both are truly amazing and go hand-in-hand with the rest of your itinerary.

I went on an adventure tour of Greece with G adventures in Sept and really enjoyed it. Took overnight ferry from Athens to Chania - Was surprised how nice the rooms were on ferry. Stayed in Chania two nights, ok town, nice snorking day trip to nearby barren islands. Not very good snorkeling, but water was refreshing. Chania has a pretty little harbor, with lots of Shops/restaurants, u can see most sites in a few hours of walking. I wouldn't stay more than a night here.
Left at 6am in morning to take hour + bus to Samaria Gorge. After coffee and snack at small restaurant at top of gorge began about 5 hour downward hike through the gorge. U have to bring plenty of water and food with u, as none available in the park. Warning the hike is not hard, however, the first third of the hike the trail can be quite steep, and is full of shale/loose rock, so u have to watch ur step. Also as the day progressed it go quite hot, so at end it was kinda like the Bataan death march. We all loved it though. Wear decent shoes, this is not a trail for sandals. Nice there is a small village at the end with a nice beach to take a dip in. Took a short ferry from there to Loutre? A picture perfect village on a beautiful bay with nothing much to do but swim, kayak and eat. Some nice easy hikes on cliffs above.

Spent several days in various areas of Crete. Would love to go back again and some serious hiking/Exploring. You will definitely enjoy. Herklion was not that interesting for me other than for its beautiful small museum. Great 2 hour or so fast ferry to Santorini. One big recommendation from me is do a sunset tour on a catamaran. We got to visit three wonderful swim spots have a Greek bbq dinner on board, your kids will love jumping off the side of the boat and snorkeling. Grande finale is watching a red sunset on the water. Also u will feel pretty smug about not being one of the thousands of tourists jam packed in Ola that u can see from the boat. Tour was about Five hours.
Personally I didn't care for Ola or Fira. Very crowded. We got there early to check out the views and pretty architecture, but then tour buses came rolling in and all the quaint little byways became jam packed. Lots of high end shopping, but I'm not into that
I really enjoyed staying in the laid back beach town of Perissa on the other end of the island. There are lots of people there, but miles of beach. Great swimming. And lots of little hikes there too. You can book any and all tours from there with pickups at your hotel. We did a two hour or so tour of the island highlights with a wine tasting, I would not go back to Santorini, glad i did it once, but will hopefully make it to smaller less crowded islands on my next visit.

Enjoy your vacation.

We booked a sea kayak tour about an hour from Napflio and fairly close to Epidavros that we're really looking forward to. Here is the website in case you're interested: https://www.panexpeditions.com/ They have shorter trips originating from the Napflio 'harbor' as well.

Wow, Im loving the ideas for things to do. Not to that point quite yet (except in broad strokes), but the catamaran idea is so awesome - we will do that!

Here's Nit-picky question as I am making my lodging reservations (I always try to get the dates set so I can find lodging because there are 5 of us and I strive for keeping prices low):

Would you do:

A.
Crete 9 nights
Santorini 4 nights
Naxos 5 nights

B.
Crete 10 nights
Santorini 3 nights
Naxos 5 nights

C.
Crete 10 nights
Santorini 4 nights
Naxos 4 nights

I know - it depends what I want to do in each. But honestly, because it takes so long to research and plot that out, and Id like to get lodging (at least on Santorini) asap, I'd like to make this decision.
Some people say 4 is not enough, some say too much in Santorini. Im also not sure Crete needs 10 (I have plotted that one out somewhat and I think 9 days would be enough...)

Also, on Santorini, we are unfortunately going during high-season (mid-July). Would you bother staying somewhere on the west coast, or just stay on the east to avoid the crush?

Thanks everyone,
Jess

Im considering dropping Athens and just planning to arrive the day
before my flight, rather than the day-before-the-day-before

Not a good idea, IMO, when you are coming from an island.

90% of the time, it's all going to work out fine. But Greece can have unpredictable weather conditions at all times of the year, like heavy winds, that will make them cancel all ferry and plane connections. I've seen it happen.

Would you bother staying somewhere on the west coast, or just stay on
the east to avoid the crush?

For first time Santorini visitors, the crater side (west side), absolutely. You want to make your visit to that spectacular island worthwhile and not just stay on just another beach. Well, the beaches are special too because they are black - volcanic - but that's not what you come to Santorini for.

Try to avoid the extremely touristy towns for your hotel stay if you want to avoid the worst crowds. Oia is beautiful, no question about it, and certainly you will want to join the crowds to watch the sunset from there, but you may not want to make that your headquarters. Thira is also very nice, but the busiest town on the island, and most cruise ship travelers get off board there.

If you pick one of the smaller villages along the rim for your stay, like Imerovigli, you'll have the same spectacular views with less crowds.

Danke Anna,

Would you mind giving me your opinion on the days-per place?

Jessica

I would recommend getting a hotel with a caldera view on Santorini. Thats going to be massively expensive but you won't regret it. You can be nicely sitting on your balcony looking at the caldera rather than being crushed by the cruise ship crowds. Because of the cost I think 10 Crete, 3 Santorini and add that day to Naxos where you can enjoy the beaches. You won't regret that change and your bank account will thank you.

I am not sure what you are planning for Athens now. Are you flying back to Athens the night before your return flight home and are not doing Athens at all? If so you might want to consider staying at the Sofital hotel its a 2 minute walk to the check in terminal. Hotel Peris is a 20 minute drive to the airport but provided a complimentary shuttle. Its a ggod property but pretty much in the middle of nowhere.

Just for fun here are more images of Naxos
A week in Naxos https://www.flickr.com/photos/stanbr54/sets/72157645113682278/
Ten Days in Naxos 2015 https://www.flickr.com/photos/stanbr54/albums/72157656336387898

Thanks Stan for the hotel recs, as we will be staying at an airport hotel the night beeper flying to Crete.

We will be in Athens one full day and one evening, arriving 14th, departing early 16th

Jessica

Would you mind giving me your opinion on the days-per place?

Sure, though that's a very subjective kind of thing. If your budget allows it, and you want to enjoy the spectacular scenery for as long as possible, spend another day on Santorini. If you feel that toward the end of your vacation, you will prefer a more restful place, make that another day on Naxos. I can't speak for Crete since I haven't been there.

I personally prefer the smaller and quieter islands, but that's really a matter of taste. And I have never been bored on any island, so I think that you will really have to decide on what your interests are, not by anyone telling you that three days on some island are enough or not enough.

Our maximum stay on a (comparatively small and quiet) island was three weeks, and that was one of the most memorable vacations we ever had, exploring every corner of this small island. We spent a two weeks' vacation on Santorini a couple of years ago, and it was fantastic. So you certainly won't need to worry about there being nothing left to see or do after three days on any island. Personally, I feel that that's when the real "Greece" experience only just begins. :-)