please help put this itinerary in order

Day 11:

The car journey between the Meteora and Athens via Delphi and the Monastery of Hosios Loukas is more than 6 hours of non-stop driving. If you want to make an express visit to the monastery and Delphi, by getting up at 7 a.m. you will be in Athens before 6 p.m.

From Athens there is no point in going to Hydra for a daytrip unless you want to see something specific there. If it's just to spend a day on a Greek island, save your time for the other islands or use it to visit Athens

To rent a car from Thessaloniki to Athens I can recommend Capital Rent A Car which I have used. They have offices in both cities.
They only have Fords (they are also a Ford car sales dealership)
A 3 days rental in June cost around €250 this year.

https://capitalrent.gr/index.php/en

Day 16 to 8: 4 nights in Naxos it's, only 3 whole days.That seems very short to me, even too short.

Day 20 and 21: You will stay a short part of day 20 in Santorini to leave the next day, even if I am not a Santorini fan, I don't see the point. If you absolutely want to see Santorini, stay there at least 2 nights. But I want to warn you that the only birds you will see there will be thousands of cruise passengers :))

In summer there are many flights between Santorini and most major European cities, some of these cities have flights to the US, but It's impossible to know at this time all the Santorini→ US flight possibilities via a European city.
You have to wait until at least December 2023 or January 2024.

If there were a way to fly from Santorini back to the US, that would be ideal, but I haven't been able to find any sort of reasonable flight schedule / price.

The flight schedule at Santorini airport is not great for people wanting to fly from there back to North America because most of the flights from Germany/Switzerland/etc arrive in the afternoon or early evening.

What if you flipped your itinerary? IE:

1. Fly into Santorini

2.Ferry to Naxos
3. Ferry or fly to Athens
4. Stay in athens
5. Drive to Delphi/Meteora/etc
6. Drop off car in Thessaloniki
7. Transit to Istanbul
8. Transit to Cappadocia
9. Fly out of Nevsehir or Kayseri airport

It is somewhat easier to find flights out of Nevsehir/Kayseri that get you back to the US at a reasonable hour. You'd likely have to connect back through IST but you wouldn't have much backtracking. I know that you want to put the Cyclades towards the end because of the weather, but if you can leave for your trip in the beginning of June it will already be fairly warm regardless. And Santorini and Naxos are great places to be jet lagged

Thank you, Jo Lui and Edwardius! Your replies are extremely helpful.

I will definitely drop Hydra (I was attracted by the no-cars and lots of donkeys, but I agree that we should add time somewhere else instead). I will add one day each to Naxos and Santorini. I know Santorini will be awful with tourists, but it is just one of those things where I know I will regret not going when I have the chance.

Agree that the flow is better starting in Greece, and it does seem easier to get home from Istanbul. I had originally planned to be in Istanbul last, but as you correctly say, we wanted to have the warmest weather at the Greek Islands. Perhaps by starting in Santorini in late May, it will be less busy? Ha! Right?

Does anyone know the weblink to see the cruise-ship port schedule for Santorini? We used the avoid-the-cruise-ship strategy in Croatia last year and it worked great!!! But, perhaps there is no avoiding cruise ships in Santorini ever.

And, finally, the car rental price for Thessaloniki sounds high. Jo Lui, Do you know if it would be cheaper out of Athens? Not expecting you to know this. I can certainly look it up.

Will definitely spend a night in Delphi. We don't have unlimited time, but are not constrained to a specific limit either. I have learned from past vacations that it is better to add a day than to be rushed!

Thanks again!

The price is high because it's with a pickup in Thessaloniki and a drop off in Athens, and it was an example with a mid-size SUV model, not a small car type.

Check several car rental companies, you will have significant drop off fees each time

If you return the car to the same location it will costs much less. This is partly why most visitors prefer to take the train or bus for the route you want to do.

Last June, with Capital rent a Car, I paid €315 for 11 days (SUV type car) wiith a pickup in Athens & drop off in Athens too.

There is no "avoiding cruise ships" in Santorini because there is not a single day without the arrival of a cruise ship.
From mid-May it’s 3 per day on average

The cruise-ship port schedule for Santorini is available here

https://cruisedig.com/ports/santorini-greece/arrivals

Thanks again, JoLui!

Understood about the car drop-off at a different location. We are very comfortable using public transportation and would love to do that if it is a viable option. I will do some more research. I wasn't sure if we would be able to see Hosios Loukas without a car. I have been trying to get the itinerary nailed down and then plan to look at details, but perhaps I should figure out some of the details first.

What I don't understand is why you go to Thessaloniki (and you only go there to take a car).

Whether you start in Turkey or Greece it would be easier to avoid Thessaloniki and fly Istanbul↔Athens.

And then, from Athens, go to Delphi + Meteora, either by renting a car or by taking the train or by booking an organized tour.

Delphi is less than 3 hours from Athens by car, bus, or train.

It sounds like you are set on Naxos, but have you considered a different island? When I was researching a trip to northern Greece (yet to take it), I zeroed in on the Sporades as a possibility but also the mainland area of Halkidiki (gorgeous beaches).
Your itinerary sounds fabulous, but I wish you had an extra week--or at least a few days! I just find the travel kind of tiring so I like to stick to one country or one area even.
It is a really tough toss-up, crowds versus swimmable seas! I assume it is swimming that is the issue, as May should have lovely weather otherwise, but it does take a while for the sea to warm up. That said, I did swim off the mainland in late May--it was after a long hike so tolerable, but it was bracing for sure!

If you are looking for places to stay on Santorini, check out the village of Imerovigli. We stayed there last month and it was MUCH less busy than Fira and Oia.

It's in walking distance of Fira town and also is in a primo spot for watching the sunset (better than Oia imo). Most tourists from the cruise ships won't make it as far as Imerovigli or Firostefani on the main walking path so they don't really bother you.

JoLui - point taken about Thessaloniki. It looked much closer to Meteora, so I thought we could do a one-way Meteora - Delphi - Athens rather than a loop Athens - Delphi - Meteora - Athens. It seemed like less driving that way. But it might not be worth the extra hassle/ cost.

Valadelphia - I don't have my heart 100% set on Naxos. I have read and read about the various islands, and that one just kept coming to the top of the list. That was before I saw that so many people on the RS forum had also chosen Naxos! We want something that is not too difficult to get to (only takes half a day; not a whole day), is not full of cruise ships, has substantial "nature" areas for hiking, has lovely Greek villages / churches / maybe some ruins, has attractive and not-too-windy beaches, and has a reasonable tourist infrastructure without being overrun with tourists. Naxos is just where I kept ending up. The proximity to Santorini is a big plus. I won't be devastated if I don't get to see Santorini, but I have wanted to go there since I was a young teenager (LONG time ago!), so that is also a factor. I would happily consider other suggestions :) I would love to know what you end up deciding on for your trip.

Edwardius - thank you so much for the suggestion of Imerovigli!! I actually had my eye on that because my brother-in-law has IHG hotel points he is willing to give us, and the IHG hotel that I identified in Santorini is in Imerovigli :) I am very glad that you found it a good location. If we can't use the IHG points, I will try to find something in that area in any case.

Valadelphia - in response to your other thoughtful comments, I am actually pretty happy with the pace of this itinerary (making the changes suggested above). We typically like to stay places 3 or 4 nights, avoiding 1 - 2 night stays whenever possible, and we mostly accomplish that with this itinerary. With overseas flights being SO expensive, we try to see everything that we really really want to see in a given area (not knowing if we will ever get back there again). Istanbul and Cappadocia have been high on my wish list for a long time, and Turkey is so close to Greece that I thought it would work well. There are so many other parts of Greece (and Turkey) that I would love to see but I think our itinerary will allow us to see a wide variety of different things (Byzantine religious art - which I love -, ruins, natural beauty, classic "Greek" villages, and a Greek island / beaches. We do hope to swim. We love a quick dip after a long day of sight-seeing. That was another reason for choosing Naxos.

Still very happy to receive suggestions!! Thank you for taking the time :)

Yes, Meteora is closer to Thessaloniki than Athens, but the basic problem (like that of many other travelers who want to go to Greece) is that you want to do too much and see too many places in too little time.

So there's no solution except to spend most of your time in car journeys or other logistical activities, not on a real vacation.

Having said that, this may be your way of traveling, I don't know...

It'll all work out--we all like a different pace. I am just trying to pin down if swimming is the priority for Naxos being last--anything to help you eek out one more day would help!
You will be in Byzantine heaven! The cave paintings in the Ilhara Valley in Cappadocia were especially evocative--highly recommend a hike there.

Thank you for the tip about the Ilhara Valley! I have not started to research the Turkey portion of the trip yet, so that is very helpful.
Re swimming, it is not that we love swimming or beaches so much, it is more that I feel that is part of the Greek Island experience, and we like to have lots of experiences. When we were in Croatia last May/June, it was unseasonably hot. We hadn't even planned on swimming, but serendipitously, found ourselves near a beach at most of our major destinations, and we ended up loving being able to lounge in the sun and take a quick dip at the end of a day of sightseeing. It ended up kind of being the icing on the cake of a perfect trip. I am not trying to replicate that, but having had access to beaches did end up being enjoyable for us, so I think we would like it again - but just as part of a varied setting :)

Regarding Santorini, we stayed at Blue Dolphin in Firastefani, which is much less crowded than Oia and Fira. The rate was reasonable in May 2022 - $230 per night. We had a room and balcony overlooking the caldera. Breakfast was an extra 25 euros for 2 people. The food was amazing and the view from our balcony was equally amazing! What a way to start the day!

https://www.bluedolphins.gr/

Thanks kmkwoo! Great recommendation!

Thank you all for your helpful input! I think the itinerary is coming together in a reasonable way:

Day 1 - 4 Cappadocia
Day 5 - 9 Istanbul
Day 9 - fly to Athens, pick up car, drive to Meteora
Day 10 & 11 Meteora
Day. 12 - Delphi
Day 13 - back to Athens, drop car
Day 14 - 16 Athens
Day 17 ferry to Naxos
Day 18 - 21 Naxos
Day 22-24 Santorini
Day 25 home

maybe a day less here or there, but this is the general flow. We could do it frontwards or backwards. I have been looking at the Santorini cruise ship schedule https://cruisedig.com/ports/santorini-greece/arrivals. It appears as if there is only one cruise ship (1600 passengers) June 7 and only three small ships (less than 800 passengers each) on June 8th. I am going to build my itinerary so that we end up in Santorini on these dates unless I am missing something. If anyone has insights, could you please weigh in? Almost every other day between mid-May and mid-June appears to have multiple thousands of cruise ship passengers. Can I trust the schedule this far in advance that June 7 and 8 will really be "safe" from the hordes of cruise ship passengers? Or is there something wrong with those dates that I might not know about?

Thank you! I very much appreciate everyone who has weighed in thus far.

Regarding Naxos, when we were there we took a day trip to the archaeological island of Delos and Mykonos. You might find the trip worthwhile. We would have preferred Delos only but couldn’t find such a trip. It was an all day trip with about
three hours on each island. No walking tours were included; we were each on our own. We were really impressed with Delos and could have spent more time there. Mykonos had a beach near the boat dock where we enjoyed a rest.

Can I trust the schedule this far in advance

It's not that far. Cruise ships itineraries are already defined until the end of 2025.

But don't worry too much about the number of visitors, otherwise you will also have to count those who, like you, will arrive by plane or ferry. And those stay on the island in the evening and the following days.

I'm sure that among the dozens of places you've already been on vacation, this is the first time you've tried to count other tourists.

Don't you find it surreal to see what Santorini can make you do, when you just want to be on vacation?

This is the magic of Santorini! :)))

You have planned a good first trip to Greece. Stay in Athens all three days; Hydra isn’t worth it since you are also visiting other major islands.

Thank you, Suki! I feel good about it now with the couple modifications :)
JoLui - I used the "avoid cruise ships" strategy in Croatia last summer and it worked great! We did day-trips outside of the port cities (Dubrovnik and Split) on the busiest cruise ship days, and did our major touristy sight-seeing before 10:00AM or after 4:00PM. It worked great! I know I won't be as lucky with Santorini, but I can try :)

It's just that this cruise passenger count reminded me this particular moment in this (old) video about another kind of count at supermarket checkouts. :))

https://www.youtube.com/watch?v=eHDow8zywaI&t=377s