Islands Decision Paralysis - September 2025

About your option 3:

10 days in Crete is a good idea but as you say it is less "islandy". If you are looking for the indefinable feeling of being on an island, as an island person having been to Crete and many islands I can confirm it.

About option 1 (Milos-Sifnos)

Totally doable, I would even say perfect. Like a few other regulars of the Cyclades islands I am not a fan of Milos but the island is different enough from Sifnos to make it worth it.
From Milos and its port of Pollonia located in the north of the island you can also go to Kimolos in 30 minutes by ferry

Sifnos being in my opinion as in that of many others who like to know the real experience of a Greek island the island not to be missed. You will find all the famous characteristics that make the reputation of the Cyclades islands.
You may also be lucky enough to be there during the Cycladic Gastronomy Festival "Nikolaos Tselementes" which generally takes place on the 3rd weekend of September during which you can taste lots of specialties as soon as you disembark from the ferry. (Sorry, I feel like I'm repeating myself LOL)

https://www.roomsinsifnos.com/

I will not make any particular comment about option 2 since Naxos seems to be the subject of a disproportionate number of posts on this forum, which has always seemed strange to me. This disproportion does not exist in other travel forums.

Which does not mean that you should not go to Naxos. I also like this island as long as I avoid staying in Naxos Town, the capital, which is now a tourist circus from July 1st to September 15th, almost like Fira in Santorini. The surrounding beaches like Agios Georgios are invaded by sunbeds (for a fee) to the point where you can hardly see the sand anymore.
I admit that imagining people who travel thousands of kilometers to spend hours lounging in the crowd in these places is beyond my understanding.
Naxos is the largest island of the Cyclades, so it has plenty of other places to stay.

I made this map:

https://www.google.com/maps/d/edit?mid=1d7GZMjFODUlB8lf7EPSXQRwu-YXaKxw&usp=sharing

The island that can be a 2nd destination if you go to Naxos is Amorgos. Here too I think you will not regret it.

https://amorgos.gr/

I made some videos, if you are not the type to watch the holiday videos of other travelers, skip them, I would not want your paralysis to get worse!

NAXOS: https://photos.app.goo.gl/XShxrwZ1ZQjGpFrz6

SIFNOS: https://photos.app.goo.gl/SKYSL1AiX8r14DQt9

KIMOLOS: https://photos.app.goo.gl/5JYKykvBkgm88oGt8

AMORGOS: https://photos.app.goo.gl/8tYWaQbm6XBEuUkp6

MILOS: https://photos.app.goo.gl/jYGrpdK5tZkufuGt7

Jo-lui -- Thanks for your enjoyable videos -- I stash them in folders next to "stanbr's" still photos. For years I've been trying to get him to Sifnos so he'll depict its charms ... or maybe I shouldn't! BTW, enjoyed Amorgos film but for some reason you didn't show its only sandy and delightful beach at Aegali, with its little hillside villages in background.

Janet, I checked the video, Aegiali and its beach are at 0:25 and 0:43.
Between 2:50 and 3:30 it's the hiking path to/from the villages overlooking Aegiali.

I have the feeling that it is difficult to get Stanbr out of Naxos anyway...
He must be trafficking Kitron liqueur and some potatoes... LOL

About Stanbr, not only Naxos .... every trip they spend 2 weeks in Crete, by now have explored the entire island ... I"ve been there i think 5-6 times, but never got farther East than Palace of Malia. They've also been all over Pelopponnese ... check out his amazing albums. It's just that they do always visit Naxos also (for years that was our rendezvous).

Oh yes, it’s true! Crete
So also olive oil trafficking!

(Now I'll stop disturbing the main topic)

I have enjoyed the Naxos banter and I have to admit, Naxos was our first island visit back in the early 1990's when we fell in love with Greece and Naxos. We have returned there for a minimum of a week and up to 3 weeks on these subsequent visits. We know local people and have developed relationships. I love providing information to other travellers who are looking for information.

As an aside for us to visit Greece it requires a Transcontinental flight then a Transatlantic flight to get to Greece. We are committed to the Greek experience.

Everyone has different interests and planned itineraries that shape how they enjoy travel. We are travellers who find a place that we really enjoy and will return frequently because we know locals, hotels tavernas and special places. We really enjoy returning to the places we are familiar with.

We have also visited at least a week in Milos (twice) Paros several times, Amorgos, Samos , Santorini and regularly visit Crete, in particular Chania and south west Crete.

Indeed I do suggest people consider Naxos when they are looking for an island destination because it is special to us and we want to share that experience with newcomers.

Ignore the haters of Milos and go. Also Sifnos. We spent 9 days on Sifnos in 2023 and loved every single second of it. We love beaches, ruins, museums, food, and there’s a ton of fantastic food in Sifnos. We spent 4 days on Roland rod and then 5 on Milos last year. This year it might be the Dodecanese islands. We took the ferry to Folegandros and then to Milos after 4 days and then at the end of our stay in Milos flow to Athens. It was a 20 minute flight. Whatever you decide to choose, make sure you get a good guidebook.

Appreciate this post and can relate to Indecision 2025 on choosing islands. Amorgos is really stunning, JoLui! Wasn't even on my radar. What great videos. Also love the soundtracks (Steely Dan fan here).

Thank you all very much for all the feedback! Although everyone has their own personal preferred island(s), it's helpful to hear about everyone's experiences.

@JoLui, what do you dislike about Milos, out of curiosity?

Are there islands in the western Cyclades that you prefer over Milos?

And yes! We'd love to be in Sifnos for the gastronomy festival, so I'm hopeful that it'll be held around the time we're there. We may need to extend our trip to make it; it's hard to plan around something that hasn't been announced yet.

@stanbr, thank you for glowing endorsement of Naxos. I'll have to review some of your posts about Naxos and re-read my guidebooks. I think JoLui's map will also come in handy.

After reading many people's experiences, both here and elsewhere, my partner and I are a little concerned that we'll struggle to have enough to do in Milos for 5 days, particularly since it'll be our first time visiting a location with a more relaxed environment.

We're starting to feel like we're forcing ourselves to want to go to Milos because it's more convenient. The main draw has been Sarakiniko beach and the possibility of a boat trip around the island - my motion sickness plays a role about whether we actually do that - but that's about it thus far.

Although it is more expensive and logistically challenging, we're currently thinking of visiting Naxos and Sifnos. That does mean a much longer ferry between the two, but I think we can live with that. It also means trying to figure out the right ordering of the two.

Quick logistical question. If we end our Cyclades jaunt by flying out of Milos and will be in Sifnos right before, is it risky to plan to ferry into Milos the day of the flight or the day before (e.g. due to strikes, weather, etc)?

Unfortunately, I booked round trip flights between Athens and Milos yesterday evening in a fit of the-Aegean-sale-is-ending-soon stress, so now I may have to change that itinerary. Oh, well.

Thanks again!

I have visited maybe 12 or 13 islands in the Cyclades (I can't count!). Several times for some, but we spent only 4 nights in Milos. It's like any place, you have the good vibes or not. My partner was not captivated either.

The particularity of Milos is that the island is almost 50% uninhabited and a Natura 2000 zone only accessible with a 4 wheel drive vehicle. In the other part of the island there are only 3 towns: Adamas the capital, Plaka and Pollonia. That's it. No other villages to explore and only basically 3 roads.

We also found that everything was more expensive and less to our taste than on the other islands, that the locals were not very welcoming and much too "commercial".

Finally 3 days was enough before leaving for Kimolos.

We are not very attracted by places that are too instagrammable like Sarakiniko beach, we would rather have the bad habit of avoiding this kind of place. It is certainly unique. I saw the beach, I stayed there 30 minutes, I think I did not even take pictures (I am particularly radical sometimes)

So this is my personal opinion which is not better than another who would have loved Milos.

So go to Milos, to Sarakiniko beach, to Plaka the nice village that overlooks Adamas, to Pollonia, take a boat trip and do not worry, it is your first trip to Greece, you will be far from being bored to death.

You have booked a round trip Athens Milos? No need to worry either. There are plenty of daily ferries between Milos and Sifnos (in both directions).
See below the schedules for September 2024, those for 2025 will be similar.
It is the week from 15 to 21. Change the week and direction if necessary (at the top of the page)

http://www.openseas.gr/MLO/SIF/2024-09-18/2024-09-18/itineraries

The ferry schedules are made on a weekly basis.
So to establish a pre-planning do not look at the exact date but at the day of the week

You can also search for those for September 2025, you will have partial results. All schedules for September will be available around July.

Note that flights to Milos are on ATR42 Turboprops, don't worry, these are very modern planes which can land and take off on the very short runway at Milos airport. But the cabin baggage cannot exceed 55cm x 40cm x 23cm, and 8kg.
Checked baggage is 23kg like on other flights.

See this video:

https://youtu.be/DJzvU8a96Dg