KLouis

Yes! Although this may be a matter of taste and others will disagree, I'll put Syros as #1 (for some, too big a city), then Milos, Paros and Naxos (in no particular order). More things to do on those four than on other islands. As for the small ones, I've listed them already (Sikinos, Sifnos, Folegandros, Kimolos, Tinos, etc.). As a potential alternative to the Cyclades, think also of the "argosaronic" islands (Spetses, Hydra, Poros), close to Athens and great in June (avoid them during the real summer and, especially, weekends).

ASUDan130

I'll be there in late may/early June. I feel like Mykonos will be sort of like Santorini in its the 2 most popular islands and have the most tourists and obviously Mykonos has the nightlife aspect which is a negative. I was just looking for a good "change up" from Santorini and Syros sounds like a very interesting option.

ballycanoe

Ios is right beside Santorini with lots of ferry connections. Ios has great beaches. Easy to get around. If you don't feel like walking there is a bus going probably every half hour in June from the port to the village to the beach then back. And don't be put off by all the reports that it is a noisy party island. I think that must be only in high season. A lot less expensive than Santorini. Lots of rooms for rent with great sea views. I like staying at Mylopotos Beach.

KLouis

This is correct, but only in part. True that in the off-season Ios is another example of a very nice Cycladic island. But just go there from June to September, and you'll see something that is really unique: the island is populated by hordes (yes, zillions!) of people aged 18-28 who all wake up between 11 am and 2 pm, run to the harbour and either sit at the cafes or loiter like zombies. They tend to disappear during the afternoon, and they reappear in the early evening till it's time to go where they spend their nights (bars, nightclubs, etc.). Yes, Ios in the summer is a place that these folks will enjoy but, really, nobody else.

jaymar01

I had to laugh at your post. The OP apparently went to Arizona State University (ASU). The place is exactly like Ios.....maybe worse.

pinniped

Bumping a semi-old thread. We're also considering a Greek island trip, but well outside of tourist season. (March 2022.)

I feel like Santorini is a must-see, especially missing the peak tourist season, and I wouldn't mind visiting 1 to 2 more islands. I've had various people tell me Mykonos should be on my list. Mostly looking for great views, natural beauty, decent hiking, interesting towns, and good food. Traveling with two teenagers - we may rent a villa instead of booking traditional hotel rooms. Prefer locations where a rental car is not necessary, but have no aversion to renting a car if that's the only way to access a particularly great location.

I know the islands can be breezy and chilly at times in the winter, but I'm okay with that. Only thing I would want to avoid is an island where everything completely shuts down during the offseason. That might rule out some of the comparatively quieter spots the OP was looking for.

Will have about 8 to 10 total nights in Greece, depending on flight availability. Want to spend a couple in Athens (we've never been there), so a week or a little less in the islands.

ahmetdouas

you can only really do santorini in March. Mykonos will be completely shut except for construction for the summer. Syros is the captial of the Cyclades so maybe there but you are really pushing your luck

KLouis

You can go to Crete. Beach hotels and tavernas will be closed but other than that, everything is open. Also, outside occasional bad weather lasting for two or three days, Crete in spring is gorgeous, with everything being (still) green, lots of wildflowers, snow-packed mountains, in two words just great!

xooz

We stayed at On the Rocks in Santorini a couple of weeks ago as a party of 3. We booked a Suite Caldera View but got Room #11 which must be an upgrade. There were 3 queenish sized beds, all with separate bedrooms (e.g. door that closes). It was perfect for us as far as size and the view can't be beat!! We spent 3 nights there and then took the ferry (2hrs) to Crete. Maybe something like that would work for you.

KLouis

Santorini-Crete ferries don't run in March. Actually, they didn't even during the pre-C19 years...

nnn

We're considering a cruise that would make stops at Rhodes, Crete, Santorini, and Mykonos in late April. (We've been to Santorini and Mykonos -- staying in hotels -- in summer.) Not going to be interested in beaches or going into the ocean. But this thread has me thinking -- will things in the islands generally be open by late April, or is it still too early? Not sure what all we will be able to do on this short stops, except maybe a day trip to some ruins like Delos.

david55

Not quite sure what you mean by " things". We only go to Crete mid-April and everything was open except for a few hotels. My guess is if a cruise ship is making the rounds at that time... plenty of " things" will be open to accommodate the tourists that disembark.

KLouis

Living in Crete for the last 38 years (minus 3-4 in Italy in between): Best season to visit Crete is March to May, the only problem being sea temperature (too cold for Greeks, my German wife doesn't mind). The second best is September to October, the water is still warm (even for me), the only problem is an occasional storm. The only "thing" that will most probably be closed during these months (perhaps not in early to mid-September) is the Samaria gorge.

david55

You live my dream.

KLouis

Most of the time a very nice dream, but every now and then a nightmare!