One month in Greece

There are some possibilities to insert another island between Naxos and Crete. The most convenient ferry options would be Santorini or Paros.

Here is the list of ferries arriving in Heraklion on June 16 and their ports of call before Heraklion.
Note that there are no ferries between the Cyclades islands and Chania. When arriving in Crete you will need to find a way to get from the port of Heraklion to Chania.

https://gtp.gr/greekferries_searchresult.asp?Code=EGRCHE70HCRHCR&AskDate=16%2F6%2F2023&IsDep=False

That being said, since you mention the possibility of extending your stay in Naxos, I'm not sure I understood correctly if you have already booked your accommodation there.

You need more time on Crete! It's (comparatively) a huge island. I hope you'll adjust your timing so you can see the mountainous interior as well as Chania and other coastal spots. I'd add the extra three nights to Crete rather than to Naxos (which is very nice but much, much smaller) or another stop. Crete's about 20 times the size of Naxos.

Thanks JoLui!
We have booked accomodations on Naxos as well as Chania. From Naxos ferry we'll arrive in Heraklion June 13 and then stay somewhere on the east side of Crete We'll have 3 nights: June 13-16. Open to suggestions. We'll be attending a concert in Vamos near Chania on the 18th. So, if I've calculated the dates right, we will be somewhere in Eastern Crete June 13-16 and in Chania June 16-19. We will rent a car, and fly out to Athens or Kalamata in the Peloponnese from Heraklion that same day. Anybody care to weigh in on flying between Crete and Athens or Kalamata?

From there we'll rent a car for our final leg in the Peloponnese, where we've booked an AirBnB near Mycenae, to use as a base, from June 19th to Saturday, June 24. We don't fly out of London until the 30th of June, so we will probably spend an additional 2 nights driving back to Athens, with the option of spending that time in Naphplion or Athens--open to suggestions for that final leg and flights between Athens/London ( Want to make sure we have enough time and not have to rush too much!)

Thank you acraven!
As you can see above that's exactly what we thought--great minds think alike and all that!
Can you suggest a place to use as a base, i.e. a "Chania" on the east side of Crete? For three nights? We will have a car and obviously want to spend a day at Knossos. Thanks so much!!

For me, a month in Greece would have to include at least 3 nights in Santorini.

I haven't been to eastern Crete. I have read it's more for beaches and less for sightseeing. I'm not a beach person, so I can't help you there, except to suggest that you reconsider where you're going on Crete!

Hi cala--just worried about all the crowds post-Covid on Santorini, that's all.

Thanks everyone! Just booked an AirBnB on Crete in Sisi, east of Heraklion. Does anyone know Sisi? Also looking forward to visiting Delos on a daytrip when we're staying on Naxos, with additional time in Santorini and Pariki on Paros. Milos looks interesting as well. Any thoughts?

When flying out of Crete has anyone tried Kalamata as opposed to Athens for landing points?

FYI: The day trip from Naxos to Delos is a long day with very little time on Delos and no guide.

Noelle,
I was thinking of going to Delos from Mykonos with an overnight in Mykonos--two birds with one stone, and a break from Naxos?

Have you checked carefully? I believe there are no direct flights to Kalamata from Crete... you would have to change in Athens.

I'm completely lost with the Birdnest schedule who now wants to go to Delos, Mykonos, Paros, Milos, Santorini while booking an additional Airbnb in Crete.

I'm afraid this will end with a visit to Rhodes from Corfu. LOL

Anyway one thing is sure, there is no direct flight Heraklion → Kalamata. You will have to transit via Athens.

JoLui, I do have a month--Naxos for six days--is there no way you would consider a ferry to another island (within the Cyclades) from there during that time? I needed a reality check--that's all I'm asking for. Sorry for the confusion.

Now that I reread your first response I see you did suggest inserting an island between Naxos and Crete. Which one, was all I was asking.

Ok birdnest, I see more clearly now :)

I actually suggested Paros or Santorini but that was in case you go there at least 3 days.

That being said, from Naxos there are daytrips to Delos, they stop for a few hours in Mykonos
You can inquire once in Naxos in local travel agencies like "Zas Tours" or "Naxos Tours". (see links below)

The other nearby islands where you can go for a day are in the Small Cyclades: Koufonisi and Irakleia. And if you like crowds, hordes of cruise passengers and Instagrammers you can even go to Santorini. (good luck with that)

All these day tours are done in dedicated boats.
In summary pretty much everything you can do from Naxos is below:

https://naxostours.net/en/naxos-tours-greece/

https://zastours.com/

https://kerrascruises.com/?lang=en#home

https://jasondailycruises.gr/en/

On the other hand, Paros and Milos are not really destination islands for day tours for the simple reason that you need at least 3 or 4 full days to enjoy them.
However, to go to Paros without taking a ferry at Naxos town, Kerras Cruises makes 2 daily crossings between the port of Agia Anna in Naxos and Piso Livadi in Paros.

And be careful not to spend all your stay in Naxos on daytrips, Naxos is an island that deserves at least 4 or 5 days to visit it

I highly recommend you focus on western Crete, not eastern.What is your reason for staying on the eastern side? Our Greek friends told us to stay in Western Crete, not Eastern Crete. We explored a lot of the area. Give your extra days to Crete, western side. My Greek friends describe eastern Crete as filled with big resorts.
And if you want to go to Kalamata from Chania, Crete take a direct ferry there.