Greek Islands -- which order?

We did a similar itinerary following the RS Greece Tour in 2017. We spent 4 nights in Santorini>a week on Naxos. With limited time I would do 3N Santorini & 4N on Naxos. We flew back to Athens for our last night. We had 4 nights in Athens when starting our tour. We enjoyed Santorini for the history & beauty, but loved Naxos!! The cuisine, beach, history… We didn’t want to leave.

It is great that we can start to plan for Greece next year.

When are you planning on going?
We too fly from the west coast (what a long haul, 24 hours of actual travel time). Never the less whenever possible we get out to our first island on the day we arrive in Greece.
Santorini is very popular so there are lots of flights including late night arrivals so we would finish the trip by flying Athens to Santorini on day of arrival. Waking up on an island is way better than waking up in Athens after a transatlantic.

Just another thought. If your flight goes to another European destination first where you have to connect for Greece ,you might want to see if there are direct flights to Santorini from your arrival location. For instance we have a direct flight to Munich where we change planes and fly into Athens. Check to see if there is a direct flight to Santorini instead.

While Mykonos is lovely it has chosen to brand itself as a high end destination which means very expensive. Naxos has everything and more than Mykonos but at half the price. Good choice you won't regret it.

Your number of days is good. Three nights is all my budget can withstand in Santorini. 4 nights Naxos is good, a week would be better. Any chance you can coax a few extra days for your vacation?
Do fly back to Athens. Three days is a decent amount of time there but in a pinch you can do the main highlights in 2 days.

Here is why Naxos is a good choice.
Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689

Naxos 2017 https://www.flickr.com/photos/stanbr54/albums/72157663620712358
Naxos 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761

Have fun planning.

Thank you, Stan!

Very helpful information and suggestions. Our trip would be the end of May (leaving around May 25).

Do your beach time on Naxos as Santorini is not known for them.

Instead of taking a separate flight from Athens to an island, you can probably make a connection on the same ticket, potentially saving considerable time. The connecting airport does not necessarily have to be Athens. A number of airlines connect to various islands through other gateways such as London or Paris or several German citiess. Then fly home from Athens. This kind of itinerary is best arranged using a multi-destination search function.

Let me paint a very rough picture: Go to Santorini for the sightseeing, to Naxos for the relaxing, and to Mykonos for the partying. Of course this is very rough, certainly you can find parties on Santorini and beaches on Mykonos and sightseeing on Naxos.

But I would make the decision on the order of the islands depending on your needs. If you need to relax and decompress before plunging into activities, go to Naxos first. If you want to see spectacular sights first and get that off your bucket list before spending time on the beach, go to Santorini first. If you are yearning for parties, Mykonos is the island for you.

Since your rough outline indicates no more than about 10 days -- even if you count Arrival Day as one of these -- you don't really have time for 3 islands PLUS Athens. I'd say skip Mykonos if partying is on the list. I've been there in late May/early June 2-3 times, and can report that there's not much partying going on until really late @ night ... the internet photos u see are probably from High season. Your original sequence is about right -- because there are more flights to Santorini, so u could get there on Arrival day even if you don't land in ATH until afternoon... the 3 nights (2 full days) is enough for the Famous Caldera View and a bit of nightlife. By following forums u already know that Santorini is not the place for beaches. Then leave for Naxos on the AM ChampionSuperjet -- you have a back deck to see the cliff-view on departure, and get to Naxos noonish. Most efficient use of time. Do try to get 2 full days for the Athens landmarks, that means flying there the afternoon before. Then u can get to Acropolis at 8 AM, beat the crowds.

Thanks everyone! This discussion has been extremely helpful in laying the foundation for our trip!