Two week in Greece in May

Whatever choices you make, you want to do and see too much for the time you have.

In your 2 projects you will only spend 1 full day in Naxos. What are you going to do?
Visit Naxos town and the port, go eat and leave the next day?
It's not worth it for an island that requires at least 3 full days to be partially visited.

I would like one island a little less common

The purpose is missed!

Naxos and Santorini are in the top 3 most common islands (out of around 20 islands in the Cyclades).

Mykonos, Santorini, Naxos, Milos, Paros being islands with an airport, they experience the most crowds. Particularly Santorini which is a real zoo from May to October with more than 3.5 million visitors per year for a population of 12,000 inhabitants.

Go to Santorini if ​​you want, stay 2 or 3 nights, no more, but you will have been warned that it is not in Santorini that you will find "adventure" or authenticity.

As for Crete, you have to stay there at least 10 days to see a small part of it.

Whatever plan you choose
try to leave as soon as possible for an island when you arrive in Athens (a connecting flight is the best option when possible)

Save Athens and/or the visit to the mainland (Meteora, Delphi), etc., for the end of the stay.

In my opinion you should go to Crete first since you want to see it, skip Santorini and Naxos, then come back to Athens and keep 3 or 4 days for Athens and the mainland

I agree with JoLui you are trying to do too much. You realistically cannot visit Athens, Meteora, Delphi, Naxos, Santorini, and Crete in one two week trip. It is a lot of trouble to go to an island. It is hard to appreciate until you do it. I would not go to an island for less than 3 nights.

We have made two trips to Greece. Looking at our itinerary may help you see what is more realistic. The first was with our young adult children and my brother in law. This was our itinerary. We went the last week of May and first week of June.

3 nights Santorini
4 nights Naxos
4 nights Nafplio
3 nights Athens

Everyone thought this worked really well except would have like 5 nights instead of 4 on Naxos.

On our second trip to Greece, we did the following:

11 nights Crete
1 night Delphi
2 nights Meteora
1 night Athens (by the airport)

We would have liked two more days on Crete.

To modify your itinerary, I would suggest the following:

3 nights Santorini
5 nights Naxos
1 night Delphi
2 nights Meteora
3 nights Athens

This is 15 nights which is what I think you have. None of these are off the beaten track. However, parts of Naxos are not that touristed and five nights would give you time to see these parts.

I would save Crete for another trip.

Or you could do one of the following:

12 nights Crete
3 nights Athens

8 nights Crete
1 night Delphi
2 nights Meteora
3 nights Athens

8 nights is not very long for Crete which is huge.

You should save Athens for last so you don’t waste a night returning to Athens for your flight.

We did a 2 week trip to Greece in 2019 and our itinerary was:
Athens-3 nights (did a day trip to Delphi with a driver--very doable but expensive)
Naxos (by ferry)-4 nights
Santorini (by ferry)-3 nights
Milos (by ferry)-2 nights
Flight back to Athens airport, overnight at airport hotel for flight on day 14.
Here's what I would have done differently:
1.Fly to Naxos immediately after landing in Athens-better to recover from jet lag on an island
2. One less night on Santorini. For us, it was one of those places we needed to see but never need to return to. Splurge and spend 2 nights in a caldera view room, see the sunset from your room, take a hike to Oia on your one day, then leave. The caldera is magnificent but the island is expensive, mobbed with tourists and instagrammers and the food was meh
3. One extra night on Milos. Amazing volcanic island.
4. Flight back to Athens and 3 nights there-including day trip to Delphi
We're saving Crete for its own vacation.

Thank you. I do tend to try to pack too much in and then scale back as I plan. I will work on reprioritizing and also plan to fly straight into the islands and save Athens for last.

We spent two weeks in Greece awhile back - 4 nts in Athens, rented a car and drove Meteora / Karpenissi / Delphi (4 nts), spent a night in Piraeus before embarking on an Aegean cruise (4 nts) and then 2 more nts in Athens before flying home. The cruise enabled us to visit way more islands than we could have gotten to on our own, admittedly short visits, but that’s what we wanted. I definitely recommend Meteora and Delphi, and Karpenissi if you want to see something off the main US tourist track. Good luck!

With all trips, it looks like I will have to come back...
Thinking I can heed your advice and fly directly to the Islands. Based on the cruise ship traffic it looks like the earlier I get to Santorini the better. So now looking to fly into Santorini (3), ferry to Naxos (4), ferry to Crete (5), Fly to Athens (3). I could take one day from an Island and add a day trip to Delphi or Meteora from Athens…or just start planning for another trip.
Thank you again for your insight.

It's not bad to start with Santorini from May 17th to 20th, according to cruisedig there are no cruise arrivals on the 18th and 4 arrivals on the 19th with a total of "only" 12,000 passengers (approximately). There will be twice as many cruise passengers 4 days later on May 22nd and 23rd.

Note that the ferries from Naxos to Crete go via Santorini and all ferries arrive in Heraklion.

For information, the price of the ferry ticket Naxos→Heraklion is 100€/person with Seajets (the only ferries providing this connection)

It's 60€ for a Santorini → Naxos with Seajets or 31€ with a conventional Blue Star ferry.

So for all your ferry trips for 4 passengers, plan on a total amount of €520 to €640.

@jolui thank you!

To be most efficient, I would consider flying first to either to Crete or to Naxos, since Santorini is in route between the two.

We were able to get our flight to Crete on the same ticket as to Athens which saved us time as we could have a much tighter connection room with a connected flight than an unconnected one. We flew United.

@BethFL I agree. I had planned to do that, but I researched the cruise ship schedule and it really accelerates in Santorini starting the 20th so we wanted to avoid some of that if we can. It will force us to back track from Naxos, but it doesn't seem like to big of a deal.

You are basically adding a half of day if travel to your itinerary.

But as you say, it may be worth it.

If you are up for it, there is a wonderful hike between Fira and Oia that is worth doing and avoids the crowds. We stayed in Oia so did it in reverse and took bus back. We did it with our young adult children in 2018.

Thank you @BethFL, that is on our list to do!:) It seems like it would add a lot, but it is only about 2hrs more. So I am hoping that the trade off will be worth it.

That Santorini hike is promoted endlesslly because it's virtually the only hike readily available on the island... whereas Naxos is acknowledged by foot-veterans as "a paradise for hikers" -- one site I've used lists over 40 widely different in length & scenery .. so if time is llimited on Santorini, you might save the lenglthy time required... it's mainly about the caldera vista and (just personally), I've found the rimside walk from Firostephani to Fira to give an abundance of Caldera views -- that is, along with a relaxe strolll in Oia EARLY in the AM (Between 8 - 10am), before cruise crowds and package-tour armies invade.

Naxos also does have hiking as Janet says. We hiked to the top of Mt Zas there. The hike along the caldera on Santorini and the hike to the top of Mt Zas are very different and we enjoyed both.

And yes, getting going early is best. But we did the Santorini hike our first full day and were not moving early. We didn’t start until 10 am. It was May like you plan. The weather was not hot enough to detract from our enjoyment. But know there is no shade (on either hike).

Thank you all! I really appreciate your insight into my itinerary, but allso all your recommendations of what to do in each area. I am now settling my schedule for Santorini (3) Naxos (4) Crete (5) Athens (3).