Greek Islands- More or Less?

Hi Bill, people on this forum like Naxos, but I think Paros looks more interesting. In Rhodes, consider taking a day trip to Symi which is a direct 1h ferry ride. In Crete, make sure you spend some time in Chania.

I have looked at Crete and Rhodes for extended stays of several weeks. So many historical ruins and history to suss out. My memory of Mykonos was just beach time decades ago, but some may stretch it out to a week or so...sane as Santorini.
If you have time, why not add in one at least and I assume you could also do these as a day trip from either smaller island if you wish.
I guess, as I am heading into retirement, I even more relish the idea of not planning every spare minute and making some impulsive decisions along the way. Maybe you can do the same

So far you have four very beautiful but touristy islands. Consider leaving out Rhodes this trip. Santorini and Mykonos are on a ferry route between Athens and Crete. I suggest looking at the ferry route map and visiting a two or three more islands on the same route that you’ve never heard of. Every island has its own character and charms. Naxos and Paros have beautiful beaches. Since you have unlimited time just go without a plan. The ferry doesn’t need advanced reservations. We often just make hotel reservations for the less known islands just a day or two before arrival. Usually for 3-4 nights but sometimes we stay longer if we’re enjoying ourselves. Then move to the next island.

We visited Naxos and Santorini after the RS Greece Tour. We spent a week in Naxos and felt we got the best Greek island experience. It has everything you mentioned on your list as well as wonderful cuisine. We enjoyed Santorini for the stunning views, cuisine and an island tour that included Akritori. We felt 4 nights was too much. 2-3 is plenty. We loved Naxos, liked Santorini. If we had another 10+ days we would have gone to Crete and Paros.

I have only been to two, of the ones you mention ( Santorini, and Mykonos )
I also visited Zakynthos is in the opposite site. But if you have time, is worth taking a flight from Athens, is very touristy also though.

The only experience I have is with Santorini. It's beautiful and our 3 night stay was about right. Suggest you end your ferry trip on an island where you can fly back to Athens (or elsewhere) so you don't have to double back on the ferry. Due to an air traffic controllers strike we had to take the ferry back to Athens and it wasted an entire day.

I have been to three of the four, some thoughts...

By "latter this year", timing is important for the islands. I feel August will be insane as Europeans, hopefully, are out of lockdown and that is the traditional vacation for many. September has always been a great time to go, October, some of the islands are starting to wind down, by November, things are noticeably slow to shut down, especially on the smaller islands, plus swimming and beach time is done.

Mykonos is a nice island, very tourism oriented, lots of shopping, nightlife, and beach clubs. Delos is just offshore, so you could easily do 3-4 nights, visit a few sights, watch some of the hedonism on the beach or join in (or avoid the party beaches for a quieter one). If the party scene is not your thing, you could do two nights and move on.

Santorini is also a tourist Mecca, including most cruise ships, Akrotiri and the cauldron are the main draws, some love it, some want to see it and move on. 2 nights for me would be plenty, others look at a week or more.

Crete is more like it's own country and not an island, it never really shuts down, though the beach resorts slow down. You could move to three different places and spend 4 nights each with no problem, doing Heraklion, or at least nearby for Knossos; Chania for just a wonderful town, and someplace else that peaks your interest. We did a beach town on the South coast, Matala, just to chill.

Rhodes, I have not been, an old friend from Sweden goes there regularly for beach time and loves it, lots of history, it is on my list. It is also the outlier of this group. The other islands are relatively easy ferries, but for Rhodes you will have to plan where it fits in the plan. Myself, I would consider flying from Heraklion, there are some direct flights. A ferry is also an option, long, and you will have to manage connections...but it might give the option to explore another island. None of the other islands you mention have direct connections to Rhodes, and a ferry will require multiple stops or connections (A connection can mean a few hours, or a few days until your connecting ferry), but as I mentioned, once you see where the ferry goes, you could maybe pick up an island on the way.

I agree with flying back to Athens after vs. taking the ferry. We had been in Athens 4 nights at the beginning of our tour. For our last night in Athens we flew back from Santorini and stayed at the Sofitel Hotel at the airport. We booked several months in advance and paid about $170. Great breakfast as well. We had a morning flight and it was convenient to walk across to the airport. This avoided the need to hire a taxi.

Agree with others about returning via plane to ATH the night before your homebound flight. I hope u have booked a departure at 10 am or later, since u are required to be in line 2 hrs in advance. Sofitel is certainly convenient if you can get a decent promotional price (€150 or less) -- it's scandalous that Greece allows only ONE hotel on airport property which then charges v. upscale rates! If Sofitel is waaay high you have a nice option with free shuttle to/from... Hotel Avra, on a beach, is 25 mins away & if you reserve the shuttle at same time as booking the room, it's free.