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When to travel to the Greek Islands? May or September

Hello we will be doing a trip to the Greek Islands either May 2022 or September 2022. Not sure which time would be better. Our itinerary will be to fly from Canada to Athens. Fly from Athens to Crete for 5 days. Ferry from Crete to Santorini for 5 days. Ferry from Santorini to Naxos for 5 days then back to Athens for 5 days. Open to recommendations as well. I’ve read a lot where 2 days is enough for Santorini.

Posted by
5550 posts

I would opt for May as there is more daylight and the tourism people aren’t weary after a long season.

Personally, 2 hours for me would be 2 hours too many for Santorini, my least favourite Greek island. Far too un-Greek and Disneyfied. Crete is a huge island and you could easily spend a week there.

Do you want beaches or historical sites or walking?

Posted by
3370 posts

We visited Greece in the month of September and enjoyed our experience. (We like to travel in the fall). That said many people on this forum enjoy the islands in late May. Either would be great. We spent 4 nights in Santorini (max 2N would have been better.) It was our least favorite. Our favorite Greek experience was 6 nights on Naxos. If we return we would stay in Crete for at least a week, repeat some time in Naxos, and add Paros/Antiparos. As far as Athens, we started our RS tour there (4N). Any interest in adding scenic/historical Nafplio? Our favorite area. Only 2 hours away from Athens. Good base to see the many archaeological sites in the Peloponnese.

Posted by
3 posts

Thanks for the information. Yes we are planning to go to Nafplio and surrounding area. Very much interested in the historical aspects of the trip

Posted by
2626 posts

Early May or late May--there can be a significant difference in temps. I like late May for travel in the Mediterranean, but I would not hesitate to go in September.

Posted by
3186 posts

We loved Santorini but haven't been to any of the other islands. We took a day trip by boat to walk up to a volcano. Unfortunately,Akrotiri was closed when we were there.

Posted by
7716 posts

Give Santorini two nights, visit Akrotiri and add the other three days to Napflion.

Posted by
3370 posts

If you do decide to visit Santorini consider a tour of the highlights. We took an amazing bus tour that included Profitis Ilias, Megoalochori, Akrotiri, Red Beach, Perivolos (lunch and beach time), Santo Wine Tour & Oia at sunset. We stayed in Firostephani and skipped the Oia part of our tour since Firostephani had the same Caldera view & is less crowded! We took the bus to Oia the next morning to avoid the crowds. Enjoy your planning.