Recommended island in the Cyclades for first timers?

Rhodes is so far out of the way in the Dodecanese Islands that it make for an awkward itinerary. Save it for a trip to Turkey as it close by.
You mention only Santorini and Mykonos which are the most touristed islands in the Cyclades. Look at other islands like Paros, Naxos, Milos. If you do go to Santorini, do not give it much time.

@Suki - Thanks, I have been looking at other islands like Naxos, Paros, and Andros. I guess I'm wondering would we regret NOT going to Santorini and/or Mykonos?

We'd travel outside the busy season in either May-June or Sept-Oct

Not sure I would consider June or Sept outside the 'busy season'

My understanding is that the height of the busy season is July-August, so I'd probably leave in the first week of June or arrive in the last week of September.

We went to Hydra, an hour boat ride from Athens, on the Rick Steves Greece tour and loved it! It is small, quaint, and is not overrun with tourists (like me!) On our own, my husband and I went to Santorini. We were glad we went if nothing more than to see what all the buzz is about. We were there in mid-September and it was packed with visitors. We stayed at a wonderful place that had a small terrace overlooking the caldera and sought refuge there after 11 am when Oia was flooded with tourists. Just too many people for us.... If you do go to Santorini, stay at a comfortable place because that will be your escape from the crowds!

The Santorini question (I haven't been to Mykonos) is such a conundrum. We went, although hadn't planned to originally. Somehow, I became convinced that it was a place that one should see, and since we would be nearby, we should at least stop. We went to many places in Greece over a month, by comparison. The difference in the experience of Santorini - it felt like an amusement park version of Greece. Everything was Greece-made precious. Oia, one of the famous towns on the tip of the island, buried its power lines so they won't obstruct the view. Sounds nice, yes, but also a little ... cosmetic. The rentals on the cliff facing the caldera, either in Fira or Oia, are magazine fancy, with prices to match. There are paths that you can walk along past these places, but some are roped off, and we were asked to leave one area that we thought was a public walkway. Every day, cruise ships disgorge a trail of people from below the towns, and offer them donkeys to ride up the steep hill to the tourist towns if they want. So there is a trail of donkeys going up and down carrying cruisers. The other areas are full of people who want to experience Santorini but not spend a lot (we were in this group). So the island felt a little like a camp set up for the sole purpose of this performance. I did not have that feeling anywhere else we went (Athens, Peloponnese, Crete, Naxos). And i definitely had experiences elsewhere that felt much more authentic and touched me more.
All that said, there is some perverse satisfaction in having been to a place first hand that is so famous. It was beautiful. It was amplified beauty in some ways. The caldera is unique, and that added to the beauty. But it was a scene, and it was our least favorite place on our trip. But since we were only there for 2 full days, I think we struck the right balance.

Haven’t been to any Cycladic islands in over 30 years, but if this helps, we had 3 full weeks this past September/October in Crete. Historic Minoan sites are in many, many places. Museums too.

There were plenty of beachgoers, toting inflatable toys, in towns along Mirabello Bay, in the northeast. And German beachgoers in Pitsidia, south-central on Crete. Apparently lots of Germans are off in late September, and head straight there.

Treat yourselves to a wonderful honeymoon stay in Kato Zakros, southeast Crete, at the Terra Minoika Villas. The beach in late September wasn’t freezing, but wasn’t super warm either, even on Europe’s southernmost island. The scenic Gorge of the Dead offers a wonderful hike, with Kato Zakros located right where the gorge opens up at its end.

The Lasithi Plateau also offers fabulous hiking opportunities. We stayed in Tzermiado, and except for seeing people driving top-down convertibles during the day, saw no other tourists in the evening, and no other hikers at that time of year.

The renowned Samaria Gorge on Crete still had lots of walkers in early October. It gets closed for the season when the rains come in October, so you’ll luck out if you want to hike it and it’s still open.

June and September is very busy in Greece for those not tied to school holidays. Santorini is only an obvious choice for people on this forum. Most others prefer their Greek islands to be more “Greek” and less Disneyfied.

If you like history, 3 + days in Athens sounds like a good start. Crete is large enough for a 2 week holiday using 2 different bases. Alternatively, if Rhodes appeals to you, there are flights of less than an hour to get there and these maybe more reliable than the Greek ferries, who are renowned for their strikes.

Tph2010,
A 2-fer option that I am forever trotting out for this very question: go to Santorini then for a complete contrast, take the ferry from there over to Folegandros. Santorini is touristy to a fault in certain parts, but still a MUST. The geology and visuals are world-class, damn the torpedoes. Then Folegandros: an isle not yet wholly given over to commercialism, with genuine agriculture, good food, spectacular views, perhaps the prettiest of all Horas and VG beaches. Plus, it has one of Greece's best-value splurge hotels AND a useful public bus (see also at least one taxi).
Endahksi!
I am done. The end.

The islands you mentioned are the most popular, heavily touristed and most expensive of the Greek Islands. Whether they are a true picture of a Greek Island is debatable. Obviously they are the islands you see in glossy travel magazines and what travel agents push on people. It's up to you if they are islands that appeal to you or want something more down-to-earth and traditional.

Going off season may help with those Big Name Islands but if you want suggestions for Cyclades Islands that may be more authentic then consider:

Tinos (a gem)
Amorgos (beautiful)
Sifnos (1st Greek island we went to)
Milos (2nd island we went to)
Naxos (something for everyone)
Small Cyclades ("small" and quiet)
Serifos
Folengandros

Here's a good link for Greek Islands to consider including the Cyclades:

https://www.greecetravel.com/greek-islands/

I doubt you'll be able to travel to Greece May-June due to the virus but there may be hope for Sept.-Oct. I go to Greece every Oct. because it's off season, less tourists, lower prices and still nice weather.

There may be enough reasons to spend a few days on Santorini, despite its grotesque tourist load. Folks have written here about ways to avoid the masses there. If you review the last two years' worth of postings in the Greece forum, you'll find what sound like good tips.

Given the many other options in the Cyclades, I'm not at all convinced there is a reason to go to Mykonos (or Ios) unless you're looking for a big-time party island. You can Google for photos of the other islands to be sure they'll offer the visual experience you're looking for.

(These comments based on three trips to Greece, but the most recent was in the mid-1990s.)

Santorini : We went there a couple of years ago ,originally not planning to go because of the tourist overload and theme park reputation. But there was an incredibly cheap flight from London on Thomas Cook Airlines (now defunct and maybe one of the reasons why) so we took it , spent a few nights and then took the ferry to Naxos .

For us Santorini was a love hate situation . We are glad we went because the view and setting is spectacular and we found our own Santorini away from the crowds. What we hated was the crowds and the tourist trap vibe, especially when a cruise ship was docked. We left that immediate the area after a quick walk thru.
We loved that we stayed in a little b and b hotel purposely chosen because it was not on the water (to avoid crowds).
We loved that we took the walking trail between Fira and Oia and had those spectacular views with almost no people on the trail. It was so nice that we walked back instead of spending much time in touristy Oia and catching the bus. It was our highlight.

Bottom line is: We are glad we went but we won't be coming back. We had the time to check it out so it wasn't a tough choice. If you have more limited time then it is a tougher call.

Naxos is another story. We just loved it. It is much more low key than Santorini, not as spectacular but beautiful in a subtler way.
We stayed in town above the harbor and not at the beach as we are not beach people.
We took the local bus to outlying villages for walks and hikes and ate fish down by the harbor. and checked out the beach area even though its not our thing. We enjoyed every minute.
It was pretty quiet but then again it was early November.
We expect to return, maybe sometime in the Spring season.(We like to return to places we really like for a second or third look to dig deeper and enjoy even more).
The rest of our Greek trip was on the mainland and we will visit other islands on another trip.
I'm sure you will enjoy Greece !

Thank you everyone who responded for the wealth of information, these are exactly the kind of details I was looking for.

My only time in Greece was in June 2017. I finished with 3 nights each on Santorini and Naxos. Yes, the touristed part of Santorini is indeed touristy, with the white buildings with blue roofs you are looking for. But there is a whole island of other places — ancient ruins, interesting towns, beaches, wineries, etc. that you can easily reach by day tour, public bus, or rental car. The ferry to Naxos was just 2.5 hours. Naxos was wonderful, not so many tourists, because there is no cruise port there. Real Greek towns and communities, throughout the island, various beaches, ancient sites, oodles of restaurants and shops too. These islands make a nice duo.

Our trip to Greece last year was in late September/early October. We had longer than two weeks, so it included Athens, Nafplio, Crete, Santorini and Naxos. Yes, Santorini does have a lot of tourists, but it was one of the highlights of our trip. We avoided Oia and opted to base ourselves in Firostefani. Our stay in our own little "cave home" at Lithies Traditional Homes was perfect with wine & evening sunsets, breakfast on our own terrace while being totally pampered by Maria. https://www.lithies.com/ One day in Santorini was spent on a catamaran tour of the caldera including lunch and snorkeling. IMO Santorini is a must if you are traveling to Greece! We took the ferry from Santorini to Naxos and found that island to be wonderful as well. It was quieter than Santorini and there are no cruise ships. We did not rent a car there, but opted for a private tour with Nicolas and Naxos Discovery Tours. He has many different options ranging from hiking, outdoor adventures and visiting the small villages. Highly recommend and some of the best money we have ever spent with a guide. https://www.naxosdiscovery.net/ We flew from Athens to Chania & preferred Western Crete to Eastern Crete; had a rental car and stayed near Vamos. Not big fans of Heraklion and for our taste, the Palace of Knossos was overrated and waste of time. Athens was our least favorite part of the trip...the historical sites are amazing, but the city itself is dirty and crowded. Three full days there was more than enough for us. Nafplio was very relaxing and we loved it there, but in my view, you do not have time to visit it. Enjoy Greece, it is magical!

We were in Greece a couple years ago with our family and visited both Santorini and Naxos. We were there the third week of May and while Santorini was crowded, it was not unbearably so. We stayed in Oia because that is where we found a large enough air bnb and walked from Oia to Fira which quite simply is the most beautiful hike I have ever done. We took the bus back. Oia was crowded at sunset even when we were there. But really I didn't think it was so bad the rest of the time.

Santorini is a bit disneyesque but I am glad we went.

Naxos is beautiful but not as spectacular but much more genuinely Greek. We split up our first day there and our two 20 something sons joined us at dinner and exclaimed that Naxos is even better than Santorini!

Personally, I would skip Mykonos as it is crowded and expensive like Santorini but without the killer views. I would visit other less tourist ed islands instead. I haven't been to Rhodes but did consider visiting when we went to Greece. The complications of visiting multiple island groups made me reconsider. Greece, quite frankly, is tougher to travel around than other European countries and you will be much happier if take the difficulty of travel into account in making choices of where to travel.

If your wife seeing blue/white painted buildings is a must you can't go wrong staying in Oia on Santorini - the views are fabulous. Rent a cave house. We didn't find the crowds to be any problem (were there in April 2016) and its easy to find areas on the island where you can get away from the cruise ship crowd - especially if you rent a car. If you're flying in/out of Athens start your trip in the islands and visit Athens last. We were going to fly from Santorini to London and got caught up in an air traffic controller's strike so we had to double back to Piraeus on the ferry. Also, if you need a night close to the airport Porto Rafti is a nice beach town nearby.

I am not sure where your interests are at this point. From reading the posts there does appear to be consensus that Crete and Naxos certainly will fulfill your wants. Both are about 2 to 2.5 hour ferry hops to Santorini and both have antiquities, great beaches, mountain villages, hiking opportunities and both offer you an authentic Greek experience. Crete of course is much larger and you will need a month to fully explore it. You can get by with two weeks if you just stay on one part of the island either East or West.

Since these are our favourite islands I won't try to suggest one over the other but I thought perhaps some images might help you decide or at least whet your appetite and anticipation for next year.
Western Crete http://www.flickr.com/photos/stanbr54/sets/72157632115757899/

Chania http://www.flickr.com/photos/stanbr54/sets/72157632117917828/

2019 Chania, Sougia and Plakias https://www.flickr.com/photos/stanbr54/albums/72157711266062752
Balos Gramovossa and Elafonissi https://www.flickr.com/photos/stanbr54/albums/72157698932695812

Naxos Mountains and Villages http://www.flickr.com/photos/stanbr54/sets/72157632110674306/
Naxos Town http://www.flickr.com/photos/stanbr54/sets/72157632094558042/
Trip around Naxos http://www.flickr.com/photos/stanbr54/sets/72157634605629689/
Naxos 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761

And for fun
Santorini http://www.flickr.com/photos/stanbr54/sets/72157632154800782/

When we arrived on Santorini, I felt like I had left Greece. It looked so Greek but didn’t act like it. Stay two nights, see the caldera view and visit Akrotiri, then escape back to the real Greece.

When hordes of tourists visit a place, there's usually a good reason. Santorini is drop-dead gorgeous and a room overlooking the caldera is magical. We visited Santorini in early June, 2008 and would love to go back and do the Oia-Fira hike and see Akrotiri, which was closed at the time.

On our first trip to Greece we visited Santorini and could not wait to leave. We had already been touring Greece for two weeks and when we got to Santorini , we felt like like we had left Greece. It looked so Greek, but we were treated differently in every situation. Most people we had to deal with were not Greek. We only returned to see Akrotiri since it had been closed due to it’s roof collapse that had killed tourists. We went to Akrotiri On our second visit , waked around, still couldn’t wait to get off that island. The caldera is awesome but once you’ve seen it and Akrotiri, leave. Go to Paros or Naxos or Spetses one of the other beautiful islands.

I think that you should try ferry hopping to Naxos, Ios and Santorini. Spent only 2 max 3 days in Santorini.
Mykonos is not something that you will enjoy from what I understood.

Rhodes is defintiely worth it you picked the right place for a honeymoon to be honest..Otherwise Milos is a great place too it has a volcanic landscape like Santorini but even more impressive beaches that Santorini lacks, oh and yea the food is just great!

We enjoyed Rhodes for a few days, interesting antiquities, beautiful beaches, but I have no desire to return except for a seafood dinner at Hazelikas Seafood Restaurant.

Nearby, the island of Kos was very interesting with Hippocrates Asklepeion, medical complex, high on the hill.
But these are Dodecanese Islands far from the Cyclades. They are close to the Turkish coast.

I think for first timers , you hit the right islands. Rhodes, Sanotirini and Crete are amazing for honeymoon. Since two weeks is also just about the right time, you have to visit the village of Oia and Fira in Santorini, the town of Chania in Crete, Rhodes Harbour and town are just a few things to mention that all have wonderful scenery under a wonderful sunset in the Aegean Sea.

I went to Crete. I did not visit any other Island yet. I thought about going to Santorini. Athens, Santorini, Crete, and Rhodes would make a fine trip. The city of Rhodes has a historic medieval old-town and the Kahal Shalom Synagogue, completed in 1577. Crete has old Venitian castles - I paid about 3 Euros to enter Koules fortress in Heraklion - Heraklion has a historical museum that was uncrowded when I was there, the much more popular archeology museum and Knossos Minoan site, and the map I got from my hotel had a suggested walking tour passing by multiple sites; Hania has a maritime museum is two lovations by the Harbor, about 4 to 500 yards apart. One branch has a detailed description exhibit with some English, about the battle of Crete in World was 2. Those who mainly just want beaches might not care so much for Heraklion. I don't care much for beaches. "The rough guide to crete" is the guidebook I bought.

Just to sum up the very helpful answers here ... in 2 weeks you can enjoy quite a varied experience in the Cycladic Isles, an ideal "sampler" for your inevitable return (Greece is addictive). THe most experienced advisor on the llist probably is Stanbr (and he also has the best/most glorious photos to enjoy). He and his bride have been visiting Greece almost annually since before 2000 -- not because they are affluent, but because their love of Greece has made them prioritize these trips above others (I'm the same; have done 13 trips there in 20 years, going almost nowhere else, have visited all islands mentioned some of them many many times).

An ideal island trilogy in 2 weeks is Crete - Santorini - Naxos (in either direction) with Athens at the end for 2-3 days. The most time-efficient method: book flight to arrive Athens AM or before 2pm, walk to other end of airport for a quick 40-50 minute flight to your first island. Then ferry between #2-#3, possibly flying last leg back to mainland. An itinerary often suggested by Stanbr and by me, for a 16-day trip (2 weeks with 3 weekends) has produced many happy responses on this forum by satisfied users:
• Fly to CHANIA in west crete.. explore, then rent car to explore southward, then N.E. to Heraklion Area - 5 days
• AM ferry to Santorini - arrive noon. 2-3 night maximum, just to see Famous Caldera View etc. - 2.5 days
• Ferry (2 hrs) to Naxos - stay at a beach hotel (if Autumn, at St.George beach next to port town). rent car 2 days to explore mountain views, ancient ruins, sandy shores, hill villages etc. - 5 days
• 40 minute flight to Athens Airport, stay at hotel NEAR Acropolis, visit ancient historic sites, enjoy cafes, nitelife etc - 2+ days

Naxos & Santorini provide your "white cube blue shutters" Cycladic visuals, while Crete, offers the other characteristic Greek building look of golden stone & terracotta roofs ... along with breathtaking landscapes. It's a win-win combination!. Use this dreary lockdown season to plan and dream. Planning is part of the fun, and it produces the most wonderful trips.