Interim Greek Island Help (please?)

We did Naxos about seven years ago. I didn't have a car but walked everywhere I could for the morning
before coming back to my wife for lunch. The pictures may help of the scenery and things I found to do
but discard the prices as now out of date

https://holidayreviews.info/viewtopic.php?f=62&t=97
https://holidayreviews.info/viewtopic.php?f=62&t=98
https://holidayreviews.info/viewtopic.php?f=62&t=99

Nice photos delboy.
We always get to Naxos as part of a Greek vacation. It really is a great destination. It has a main town with a an active harbour and a maze of back alleys all the way up to a Venetian era Kastro. It is popular but still not too busy in early June. You will have to make sure you make a dinner reservation though because of the people out at the portera will be wandering back on the waterfront all looking for dining options. Naxos has lots of beaches particularly along the west coast all serviced by the local ktel bus system. It also has mountain villages in the interior to visit and to do some hiking.
You will wish you had another day in Naxos because you will not have seen it all.
If you choose Naxos I would suggest you find a hotel at St George beach. Its part of Naxos town just a 10 minute stroll around the headland.
Here are some images of Naxos
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Naxos 2025 https://www.flickr.com/photos/stanbr54/albums/72177720329571437/

Some of my favorite islands are part of the Cyclades but not as crowded as others.

Amorgos
Tinos

Both are reachable by ferry and still retain a lot of their "Greekness"

It's always hard to find a "right" island but that depends on your interests.

If you want an island(s) easy and quick to get to then consider the Saronic Islands like Aegina, Agistri, or Poros.

With four days they may fit the bill as they are not large but still have plenty to do for the 4 days.

Thanks for the great input! Now I'm wondering if we should just go straight to Crete, but stay on the other side for the 4 nights? Any thoughts?

If you want easy transfers and you have to get to Chania, then Milos is the obvious choice. And because you mention to prefer an early evening departure from Athens, I think you will have to fly. Olympic Air is daily at 18.00 and Sky Express at 19.00.
The other option is a (late) evening ferry that leaves from Piraeus for Milos and Crete. There used to be only Minoan Lines at 21.00 but from this year there is now also Blue Star Ferries at 22.00. Other ferries to Milos are either in the morning or sometimes at 14.00.

Crete is very large. We spent 11 nights on only the Western side and really needed a couple more to see what we saw well.

So you could easily spend all your time on Crete.

It really doesn't have the Cycladic architecture though. But my son who had been to Naxos a few years earlier with us told me that it was like Naxos, only better.

Much as I love Naxos the consent of just commuting to Chania by air is a good plan. You can spend a month in Crete and not see all of it. Every island hop uses up a half of a day. If you just fly to Chania from Athens you will have lots to do in Crete.
Some images
Wanderlust tours Chania https://www.flickr.com/photos/stanbr54/albums/72177720318394812
Chania 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318408008/

Chania 2022 https://www.flickr.com/photos/stanbr54/albums/72177720299646015
Theotokopouluo Street https://www.flickr.com/photos/stanbr54/albums/72157632118491316

Go to Naxos !!!

And yes you can get a ferry to Heraklion from Naxos. .

Ps - we are freaks and didn’t love Crete. We spent 4 nights in Heraklion ( the museum there is worth it as is sea fort , but that’s it ) and 5 in Chania - well the beach isn’t great - and the town is just a mass of tourist shops selling junk made in china and touts trying to lure you into their restaurants.

But I get you have to go meet family , so try naxos or Paris for a completely different feel

Going to Paros or Naxos and taking a ferry from there to Heraklion when you have to meet family in Chania is probably not the best option. You arrive in Heraklion in the evening and then it's a 3 hour bus ride to Chania.

I loved Naxos, Santorini was way too crowded and I was there at the very end of tourist season. How about flying right to Naxos when you get to Athens. Naxos is a great place to relax and get over jetlag. Then fly to Athens for your 2-3 days there and then fly to Chania.

Thanks for all the great input! I'm going to check out going to Naxos first, then Athens, then Chania which may work out better logistically.