Two initiaries

First of all, Naxos is the largest of the Cyclades.
Secondly, you can either stay in Venetian part [Kastro] - a more unique experience, or try for simple beachfront rooms/stds from Agia Anna onwards-Prokopios/Plaka] - it's still not high season in Naxos at this time, so don't panic - there are many rooms on the beach at the price range you suggest [the Kastro is another matter, although I am not sure of prices, just do a check]
Koufounisia is not as touristy as you may imagine.However, you may need to book from now - either through the internet [perhaps a slightly more expensive range] or the local rooms via phone only.
You may be required to send a deposit. The Keros is a well placed hotel.
Donoussa and Irakleia are too quiet and not as picturesque [for me] but that is all relative-and prehaps easier to find accommodation as demand is not as great.

I love Amorgos, stay at Aegiali, hire a scooter, try to find a room at Uranos pension. [or try for the village Lagada]-

Naxos-Milos-Folegandros - no ferry connection off hand, - why not try Sifnos-Milos -Folegandros
[there are fast ferry connections with either Hellenic seaways or Aegean speed lines]
For Sifnos, either Playts Gialos or Apollonia [Ano Petali] -Milos [as you suggest] and Folegandros - stay at Chora [not many choices anyway] and this is not beach front accommodation [this also applies for Plaka in Milos]-

Naxos: Great destination, as #1 said already.

Folegandros: Except Hora, which is a great place to stay, there are hardly any settlements worth being called villages, so be modest on sightseeing. And consider that most tourists need to be staying there, making the place look more crowded than it actually is. You’ll have some (even demanding) walking to do to reach most beaches (bear in mind steep ascents on your way back), landscape, however, is great.

Milos: The island is less dependend on tourists due to its wealth from quarries, that means you will find less touristic infrastructure compared to other islands. Adamas (harbour) is rather business-like, Plaka is very nice. However, since there is little public transport you’ll need to be going by either taxi, scooter or excursion-boat (good beaches on the south side) a lot. There are stretches of dramatic coastal landscape, but the whole island is rather not “typical”. I would guess that you won’t find flights Naxos-Milos, however there is some new airline going around the Cyclades with a small seaplane, maybe they’re going there…

Amorgos should be your choice: Several typical villages, dramatic landscape with monasteries, good enough beaches, hiking trails. Koufonissian islands have slightly better beaches, but otherwise are quite small and rather flat. Unlike Folegandros and Milos, all these are good to reach from Naxos (daily, I think).

Or, as #1 suggested, take a closer look at Sifnos and/or Serifos.

Nautiker sums up things pretty well-

there is a report here about the beaches on Amorgos choose amorgos
It has great beaches, but you need to know where to go.

The small sea plane is www.airsealines.com but it doesn't fly from Naxos-Milos.
To get to Milos from central Cyclades [Naxos] you can do this-
Naxos-Ios-Sikinos-Folegandros-Milos -
Naxos-Ios ferry is daily
Ios-Sikinos-Folegandros must be regular as they are near, check schedules www.gtp.gr<BR><BR>

First, a big thank you to both of you! It's great that people like you provide information and help.

What would you two suggest we do for a true greek experience and a no hassle holiday? I chose Naxos since I can probably fly there, the same goes for Milos. Would you go to Naxos, Amorgos and one of the small cyclades? Or is there a better option? Sifnos, Milos and Folegandros also sound very appealing. should I not be able to fly to naxo or milos, it would probably be easiest to fly to Athen and then take a fast ferry?

dianab1: when does the season start in naxos? do you think it's not necessary to book a room ahead?

Thanks again for the big help!

Roger

#4 don't worry yourself too much about which alternatives to choose, or about 'true' greek experiences. All islands are interesting in their own own way and there is NO 'correct' choice. Culture and tradition takes some time to appreciate anyway.

No problem in principle flying to Athens then taking a fast ferry -- even the Blue Star ferries get to Naxos in 5 hours. Incidentally, if you take a Blue Star ferry, it's worht the extra 2.50 euros to get an inside 'air seat'. The deck class can get hot and crowded. The catamarans have only reserved seat.

The season is starting up on Naxos. Booking a room in advance is not a bad idea if you want to stay in the hora (old section), since there are not many rooms available. Finding a room at one of the beach areas will not be a problem. For the Hora, try Despina's pension (tel 22850-22356). Rooms # 1,2 and 5 have balonies with sea view. Rooms 6 and 7 have balonies overlooking the laneway. Rooms 3 and 4 have windows overlooking the town and sea. Avoid room 8.

If you want 'tradition' then spend some time on Naxos visiting the inland villages.

Aegiali (on Amorgos) gives you the nicest combination of a decent beach, and proximity to inland villages and some nice hiking. Season is not yet underway and most places are at least half-empty. Some people even meet the 1am ferry offering rooms.

About ferries: there are surprises every year. For example, I noticed a once a week high-speed connection between Naxos and Folegandros. There was even a once a week link between Amorgos and Ios-Santorini. But, some of these connections are highly seasonal and privately run operations. If you have the time and inclination, it is sometimes a good idea to wait until you are on the islands and see what's running where -- and then make final plans accordingly.

About the lesser cyclades: they may be small but they are not necesaarily the best choice if you're looking for traditional island life. The percentage visitors-to-locals can be so biased in the direction of visitors that these small places feel as much like resorts as do the more famous places. But, it's up to you. If you want a peek, you can take a one-day tour from Naxos (one day a week). Or, if you stay on Amorgos, you can take the Scopelitis (small ferry) morning ferry (usually 7am departure from Katopola) to one of them, and then take the Scopelitis back to Amorgos in the afternoon.

It seems to me that you've just repeated your inital question, obviously we haven't been really helpful so far... ;-)

So, me too, I'll just repeat my answer, only scrambling the words around a bit. I have to admit: I haven't been to Naxos and Amorgos so far (but to Sifnos, Milos and Folegandros), so I can't really comment on those two islands. However, I will be going there this autumn and from what I have read, heard, seen and otherwise generally researched, I would say that these two islands are already enough for 11days. Both islands each offer everything you could be looking for: Lively places and quiet villages, popular beaches and secluded beaches, historic sights, great landscape, hiking trails. I can't see any hassle. I don't think that you'll find other two islands with that variety nearby. This should be the "better" option compared to Milos/Sifnos/Folegandros, if you want me to spell it out. If feeling adventurous, I would try to reach Astiplea instead (but it's mostly night-ferries going there), skip the Koufonissia. But please make up your mind yourself.

I've never had trouble getting some kind of accomodation on Greek islands, even during high season. There will always someone be looking for you at the harbour/airport. Just in case you're looking for a special place and want to book in advance, I'll disclose some of my plans to you (but don't show/tell anyone else!): In Naxos kastro, the Chateau Zevgoli sounds nice (it's in the LP, too, so hardly a secret place). On Amorgos, Aegiali is more of a tourist spot, Katapola a lively harbour town and Hora the central and typical place I would be going for.

may I add to Nautiker- Aegiali is very quiet - as is Katapola - there is hardly any nightlife in Amorgos, perhaps a lively tavern or cafe at night. Aegiali has 3 villages nearby - Ano Potamos [next to the sea] but elevated where you may still get woken up by the donkey. [here is the accomm I suggested]Potamos actually conencts with Aegilai, - you can walk down and go to the bakery for fresh bread for ex-
You can enjoy a lazy breakfast at the taverns, overlooking the sea, and watching the fishing boats arrive-
you can go to many beaches nearby, [3 across Aegiali beach by water taxi] or just stay in Aegiali itself. Langada and Tholaria are nearby, 2 traditional villages.

Chora is located on the top of a hill, and is always very windy. There are a few new"age' restaurants, creperies, and some local taverns, but nothing compared to the taverns at Aegiali. [no fresh fish etc.,]
There are some rooms, and in general, there are churches everywhere. One good main square, with a plane tree, a great cafe, with superb sweets.

I- on the other hand am a fan of the small Cyclades, in particular Koufounissia. What oldpro says is correct- many of these have developed out of the need for tourism, although there are hardly any resorts, only small hotels and rooms,but I personally have never seen a match for those turquoise waters, not to mention the whitewashed pathways, abundance of lobster,etc
Naxos is a large island, many long distances, very green, with some traditional villages, great beaches, although not a very picturesque coastline, a great Chora [or town] with much to see - in short.

<blockquote>Quote
<hr>On Amorgos, Aegiali is more of a tourist spot, Katapola a lively harbour town and Hora the central and typical place I would be going for.<hr></blockquote>

I also want to qualify this statement because it is not correct, insofar as it implies that Aegiali is touristy while Katapola is not. They are both (moderately) touristy but in different ways, and have quite different ambiences. Aegiali has something of a laid back resort feel, because of the good beach (this might explain the 'touristy' label). However, it is a very small place and the hill villages have very little tourism presence. You can feel very far from everywhere at the north end of the island.

I felt that the ambience of Katapola was more touristy in other respects. Perhaps because of it's more central location, larger and closer to the more populated part of Amorgos, it is also busier and gets more convenient ferry traffic from Naxos, drawing in more visitors aiming for the famous monastery. Stay in Aegiali for a few days and when you then arrive at the center of the island, with the traffic circle outside the Chora, boutique souvenir shops etc., the 'Cash and Carry' supermarket on the hill above Katapola, you might feel as if you've arrived in a major metropolis (relatively speaking, of course). It is all not quite the gem of isolated tradition that one might think. Katapola is a good base for hiking excursions in middle and south Amorgos, though.

In fact, when I was there last week, on any given day half the tourists in Aegiali (eg, 15-20 in all, not counting Greeks) had actually bussed in from Katapola. They did the hill town hike, enjoyed the beach, then bussed back to Katapola in the evening...

about prices -- I imagine that room prices would be higher in July. As of early June, double rooms with AC, fridge, and TV started at 25 EUROs a day (eg at Christine's pension). Other first prices quoted to me, for pensions scattered around Aegiali, were up to 35 EUROs for studio facilities. I didn't bother trying to bargain the prices down. Considering the occupancy rate, it would have been possible.