Suggestions for Greek islands to visit

Should we choose Naxos or one of Ionian or Dodecanese islands ?

If you do NOT have a very specific idea for why you want to go to any particular island or location, then make your choice on the basis of logistics (travel) convenience.

You have fixed the mainland, and Santorini as one island. Depending on when Santorini slots into the itinerary, then Naxos would be the logical choice. Dodecanese means more travel/money concerns and a less logical fit and no big advantage if all you want is another island. The Ionian islands are also in the wrong direction, as it were .. unless you started there.

Anyway, if you avoid the obvious 'party' places such as Mykonos, any island will do.

We are thinking of taking a typical 3 day classical Greece tour for covering Olympia and Delphi. Right decision ?

There isn't a right decision. It comes down to convenience and personal preferences. I do not like tours, preferring to move around at my own pace. However, this requires more time. If your time is limited (and/or you just prefer guided tours) then a 3-day package solves the sometimes tedious logistics issues of getting from A to B. All I can advise is to check the detailed itinerary, what parts of the day you're traveling (during day eats up sightseeing time), how much time you actually have for the attractions. Package tours are good at making big promises about the magical places you visit, but don't necessarily give you much time to enjoy the magic.

Olympia and Delphi are far apart, and both not close to Athens. "not close" meaning 3-4 hours or more road time. Do you have any priority here? A tour just of Peloponnese might let you see/visit more with less road time.

How many nights are required on a minimum for Santorini ?

Well, technically (logically), one night is a minimum. The better question is: what do you want to see/do? Some people go for a week break. They want to relax and not bother with anything else. If a person mainly wants to have a general look around the caldera rim villages and visit the archaeological sites and main museum ONLY, then a day and a night ought to give you the time you need. You should make a list of what you want to see/do. That will tell you how much time you need.

Also, how you get to/from Santorini, and arrival/departure times imposed, might have a big effect on how you can time your attractions. With the same 'to do' list an inconvenient arrival/departure times of ferries/planes might make a 2-night stay more practical.

Just in case you don't know, inter-island flights are not that common. Most flights are out/back to Athens, and to get to another island might mean transfer at Athens. So, check the travel options before you fix a plan.

Is the water too cold for swimming ?

Perhaps. Jump in and see. I've gone swimming in February. The sea is usually full of swimmers in May. Some find it too cold to swim (a minority). Some find it cold but refreshing. Some don't find it cold at all. I'd take swimwear under the assumption that June will be fine.

We visited Delphi, the sites and the history is amazing. We did a coach trip from Athens to Delphi and had a good experience. It included lunch in a restaurant in the mountains of Delphi. If you are planning to do a 3 day trip however for Delphi/Olympia, it's up to you but I think that might be a lot. Again depends on what you are planning to do and your interests, etc.

Have a blast! Greece is amazing.

to add to the great advice given by #1:
personally, i like crete a lot. yes, some parts of it are very touristy. but its a big island and you can escape mass tourism. its also very varied and offers pretty much everything: beautiful scenery, small villages, orthodox churches, ports, good hiking opportunities and more. also as you are into archeological sites, i'm sure you would enjoy knossos. as already mentionned, its a big island and i would only go there if you dont mind renting a car. and i dont think i would bother if you have less than at least 3 full days there.

i dont think that there are any direct flights between santorini and heraklion. so to avoid having to fly via athens, if you want to include crete, i would start on one of the 2 islands, and finish on the other one.

Thanks all for your valuable input. We think what bthdth does make sense on choosing island on logistics, we are exploring Naxos and most likely will finalize that. Crete is great, but considering the amount of time we have left, we guess we might not be able to do it justice. Next time, its Crete and Ionian/Dodecanese islands !! :)

As for the tour, we also prefer travelling alone on our time, but are choosing the tour because travelling by public transport is turning out to little cumbersome (changing multiple buses, etc.) and we don't want to drive so much. Thanks JanuarycVeryOwn for sharing your experience.

Last question, in Santorini, as per our research, Oia is the best place to watch the sunset. Does it get too crowded in early June with tourists ? Are there alternative places with similar views but less crowds ?

The best overall sunset views are from Imerovigli, not Oia. And yes, it gets VERY crowded in Oia at sunset time.

If you are interested in archeological sites, you should go to Delos Island. It can be reahed by excursion boats only. Most of them start at Mykonos.
Creta has 4 (ruined) Minoan palaces, some Roman sites and many medieval fortresses.

What is your research? Rick Steves? Brochures? or actual 1st hand knowledge? That Oia sunset has been ballyhooed to the max on TV travel shows and travel agents who get big hotel commissions. Of course, the sunset in Oia can be enjoyable if you have your own balcony in a well-placed Oia $$$ hotel. But for ordinary non-luxe tourists who are staying elsewhere, it's a somewhat different experience(and I've been to Santorini 7 times so this is not a "one-off" report:

Starting about 6-7 PM jam-packed island busses arrive in Oia, plus tour-group busses. The time I was pressured into the Oia-sunset madness was offseason, yet the rim-side path was packed solid w people, elbowing each other for camera angles, NO place to sit for wait of 45+ minutes. At sunset sun slid behind clouds, everyone applauded (like a theatre?!!) and all rushed madly for the island bus stop. Like NYC Times Square rush hour. Over half-hour before could wedge selves onto 3rd bus. My companions were abashed & said, ok, tomorrow we'll try your idea.

My position is that the sun goes down in the West all along the islands 12-mile length; choose what suits you. Some places I've enjoyed: (1) large roof terrace of FIrostefani's Sunset Hotel, seated in comfy upholstered loveseats. (2) In lawnchairs in FIra's famous Franco cafe -- but that was 15 years ago when a drink there was €6!! now I think it's €15-18 or so, (3) several other rim-based cafes (Volcano??) at northern fringe of FIra (4) from the "porch" of FIrostephani's oldest taverna (Aktaion), which is about 20 feet from rim path; you need to stop by early to reserve, & to get/hold table arrive by 7 or so for 8:30 sunset, but u can be eating/drinking (5) my fave the last 2-3 times: rooftop level of STANI taverna, Fira, north edge of Fira -- stop by earlier in day & book best table for 7:30 or so, they WILL honor with reserve sign, splendid view, traditional menu, great prices, relaxed enjoyable experience.

Our research was from Google and not 1st hand information since we will be travelling to Greece for the first time (and hence, the question on LP to get 1st hand review! ). travelerjan, your experience at Oia sounds exactly opposite of what it should be, hence Oia is now off our list.

Thanks brotherleelove and travelerjan for the sunset locations, will check them out.

Delos may not work out for us on this trip, meckerdv, but it sounds interesting, so definitely an island to visit for future trips! :)

No no no -- I didn't mean for Oia to be off your list, just not for Sunset. It is definitely a MUST-SEE. The secret is WHEN. In last few trips (late may-early june), I and my travel pals have stayed in Firostephani which is just north of Fira Town... walkable in 10 minutes to Fira Square & fira Nightlife, but fortunately, NOT visited by tour groups, and serene day &night. But we certainly DO visit Oia.
Firostephani has a bus stop on the mainroad, which is right out th back door of its rimside hotels. We take the first convenient bus -- about 8:30 AM, and arrive at Oia just before 9. Town is very uncrowded then, and the light is just right for photography, sunny but lots of good shadow. One can wander all over the village, enjoying the beautiful views, taking great pix (on Santorini, you cannot take a bad photo, even unskilled as I am).

You'll also get a giggle out of the latest phenomenon -- the "Japanese Bride". It's become a fad for young Japanese women to have their pre-wedding photos taken in Santorini .... and then they go back home for the actual wedding (and some of these I hear don't even have a fiance yet, but are in hopes). THey're all over the place, posing in white gowns (feet, unseen, are in flip-flops).

Around 10 AM or 10:30, the throngs of tour groups, from package tours or Cruises begin to clog the narrow lanes, so it's time to leave. THese groups tend to return to their busses and cruise ships around 4 pm, so the village becomes peaceful again until 6 or 6:30. So Oia can certainly be enjoyed if you time it right!