First time in Greece-going solo

Option 2 certainly puts you in the end-of-season category for the islands, but that has as much to do with tourist density as the quality of weather. 'Cold' is a subjective term; Average temperatures could range anywhere between 20-25 celcius. That will probably feel 'cold' to you, if you are arriving from Thailand.

On the positive side, it should be OK for swimming, since sea temperature is a lot more stable than air temperature, and will not have cooled down much from the summer.

If you want to go with the odds regarding optimal weather, then pick option one.

In Greece, the dry, warm summer wheater guarantee ends normally in the second half of september. Afterwards, it may be fine or it may be rainy (normally only for a fwew hours). Furthermore the greek islands you mention are rather windy. The sea water is still warm. If you want greek culture, greek cuisine and fine wheather until november, you must go to Cyprus. Or combine the two: visit the museums and greek temples of Athens and fly then to the beaches of Cyprus.

Hello,
I believe the rain also starts about the beginning of October. I spent a few weeks on the Peleponnes some years ago in Oct.. We met a local on the bus and she told us we were lucky to be having such good weather. You never know these days though. The weather is really getting crazy. A lot of the shops and restaurants on the islands close up at the end of Sept. (which is basically the end of the tourist season.) until spring.
On another trip to Athens, Naxos, Paros, and Santorini in March I noticed many shops/restaurants were still closed. I think they really get going about Easter time. That was no big problem though, there were still enough rooms and restaurants to go around. Actually it was better for me because it was much quieter and relaxing.
I personally think Athens is one big, stinky,(exhaust fumes) and loud city. If that's where you fly into then go see the Acropolis and the museum and then get out of town as fast as you can so you will have more time to relax on the islands, otherwise skip it all together. You'll be on a tight schedule anyways if you want to see all that. The ferries can take a while. The ferry from Pireus (Athens) to Santorini takes 9 hours. Stay loger if you can. Greece is about the only country where I have gone back time and time again. If you don't play Backgammon then learn it before you go. They'll have a Backgammon board in every cafe´ or old man coffee house in the country, just ask for it. It's so nice to sit under a big shady tree at some coffee house playing backgammon, drinking a Frappe´,(almost a greek national drink, iced coffee with a head of foam on top) and just watching the world go by. And the world does turn a little slower there than in other parts of Europe but it's nice and relaxing, so enjoy.
Have fun

Thank you for all your replies =)

I feel a bit relieved now and I guess I would go for my first option as i m already travelling alone and i dont want to see the whole place so empty.

This would mean i'm going to have only 8 days, thus i might have to give up at least one place.

Will they still have party scenes going on Ios at end Sep? If not, then i ll just skip that one. Otherwise, what do u think i should cut off from my list?

Will the dive centers still be opened at that period? I ve checked on Padi's website and there are quite a few certified dive centers on Santorini but nothing showed up on Paros. From all the 4 islands I have mentioned, which one is the most recommended for diving?

=)

Tropicalpeach, check out Blue Island Divers on Antiparos. It's a ten minute ferry ride from Pounta on Paros.

Ios will probably be fairly quiet by the end of September.

“If you want greek culture, greek cuisine and fine wheather until november, you must go to Cyprus.”

I can’t let this go… #2, are you kidding? The most over-crowded, over-rated, desecrated-by-mass-tourism island in possibly the entire world, currently in the grip of the Russian mafia (allegedly, I guess I’d better say here), and in thrall to unscrupulous property developers who have managed to chuck up hotels on several supposedly protected natural areas – you couldn’t ask for a worse model of 21st century tourism. My guess is that no-one who loves the Greek islands would feel comfortable here – as I found out to my cost a few years back. The weather in autumn is nice, I’ll give you that.

Septemper is the mildest month in Greece and probably the best one for holidays ,the beginning of October it might bring some clouds in the islands and some times (very rare) a tiny rain just to wash some dust from the cars... I remember our school parades in Athens for the Greek National holiday of OHI (28 of October) were always held in sunshine (well that was some 40 years ago and the climate has change a lot since then, but still October is generally a mild month for Southern Greece). As about the islands, my favourite ones Ios Paros and .Mykonos where at their best in Septemper

Dear tropicaltraveller, I suppose you only know Aya Napa/Protaras, Larnaca and Paphos. But that's not Cyprus! Walk from Kalavassos to Governor's Beach, from Polis to Fontana Amorosa (one unspoilt beach after the other) or visit the absolutely deserted sandy beaches near Apostolos Andreas, walk in the Troodos mountains admire the frescoes in the local churches, sleep there in a small village hotel or in a monastery........