It seems that many fellow posters seems to forget to mention a very critical matter to mynard .During the winter, especially January there are strong winds that sometimes their forces are over 9 Beauforts and as you know all NO ferry or any passenger boat lives any port. Sometimes those gales can keep for days even weeks so imagine if you are trapped on an island while your flight has gone. I agree with Thrym that the mainland has much more to offer in the winter (many Historical sites), places like Meteora ,Pelion with its beautiful villages, Parnassos and Arachova, Ioannina ,the Prespes lakes ,the waterfalls of Edessa, Kastoria ...ech and not to mention the numerous Ski resorts on the mountains of Greece.

My thought would be to abandon the idyllic Greek Island vacation and focus on what would be feasible, certainly the mainland and Peloponnese, but also the larger islands served by air as well as ferry. Naxos, and Crete being the obvious, but others based on availability of rooms/restaurants/transport etc. Even Athens can be more lively in the Winter as the Greeks are home more than in 'season'. I think Greece could be very nice this time of year.

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<hr>even weeks <hr></blockquote>
tsk ... you're not serious ...
One more time ... "more to offer" is making an assumption about what any one person wants to do, and the OP hasn't said anything on that score yet. ALL of the advice about the mainland would be completely off the mark ... in other words, not good advice ... if compared against all the people who, for whatever reasons, DO make a tour of various islands in the winter. They do that because they want to do something other than check off the archaeological sites. There are other reasons for visiting a country. Surely that's not difficult to understand.
Perhaps the difference in perspective is that I don't see the world through the filter of the tourism industry. That's not how I plan trips. I view a country as a place where people live out their lives. Visiting in winter is NOT my way of avoiding tourists -- that is irrelevant. I visit in winter as a way of getting a different angle on Greek life and contemporary culture, to get a feel for place and the passing seasons. After all, I live in my 'home' countr(ies) on a year-round basis.
The OP may be just one more uninformed poster who thinks it's always summer in Greece. That misconception is easy to clear up. But I read the OP and take another possibility into account: that here's someone with a bit of imagination and adventure. Just in case ... my word of encouragement is: set aside the misconceptions about Greece in winter and follow your whim. Why would anyone suggest that they not do that? There are a lot of interesting and unexpected experiences to be enjoyed.

OldPro - just read your #6 - you misunderstood me - I didn't mean I preferred the mainland in winter because of the weather - I just meant there was more going on - whatever you like to do with your time. Plus, my story about my friend's Cretan husband finding the winter dreary in Crete is very much to the point, I would think - he's a local, he grew up there and he sort of knew what to expect - however, he found it much more boring and depressing than anticipated - how much more depressed a visitor who knows nobody on the island would be! (It was his depression about the whole winter-in-Crete scene that changed his mind about where to live, not the weather specifically - the depression, however, was probably precipitated by the weather conditions). Obviously (at least I would have thought it obvious) overcast weather is going to have a strong effect on one's mood and if Crete is relatively empty of travellers and many places are closed, the weather is not going to help. Even if you are the sort of traveller who just likes to hang out in cafeneions and try to get to know the locals, you could find yourself craving something else to do/to go to for a change. The mainland has more going on, more eating places open, things to do, etc, so I thought it was a better choice in indifferent weather conditions (Thrym has already said this in #7).
Reading what you say in #12 I take your points but I honestly haven't met so very many travellers who really are happy to just hang out getting the feel of a place and the culture (though I am like you about this) so I suspect that chances are high that Mynard wants to see a few sights and do a bit of a tourist thing too - anyway, you are right, we need to know what Mynard likes to do!

Dear oldpro I am not going to a debate about it, but be sure I have spend many winters in Greece and the Greek islands and I know very well the life there in the winter. Yes we have winters that the weather can keep for weeks with rough seas and no ferries. Most of the upmarket islands are nearly dead during this time and in many you wont even find a restaurant open, as about the locals (men only because you wont see any Greek woman in a kafeneio) does not spending their times in the traditional Kafeneia as you know them as a tourist except some old fishermen that hardly speak any English, instead they go in other kind of Kafeneia the so called Leskes (gambling clubs) to play cards and for sure you will not go in a such a place to "meet the Greeks and their culture" on the other hand the expatriates (Europeans mainly that have bought houses on several Greek islands or have been married to Greeks) will be the other choice as they have create their closed communities and go to their regular places ,but you wont find any Greek culture among them instead probably ironic comments about the locals as far as I know <blockquote>Quote
<hr>Very well<hr></blockquote>.
And finally mynard after reading all those posts probably he can make up his mind if he wants to see the Greek islands or the Greek mainland in January.