We loved Oia!
A week would be nice.

Two nights would perfect. It's all about looking at the view, very touristy at times. Seems to exist for tourism rather than be a real place like Paros or Naxos. Check cruise shipmarrivals and choose dates with fewer ships in port.

I vote for Oia too, though I think you need at least 3 nights there. Yes, Santorini is touristy ( more so in July/Aug! ), but it's still one of the loveliest place I've ever been to. Maybe you could spend 3-4 nights on Paros/Naxos too, that would give you a different island experience.

My vote goes for Oia first, then Imerovigli!
I originally planned for 2 nights, but ended up extending my stay to 4 nights ;D I stayed in Imerovigli, although I was happy with it, I can't help to regret not staying in Oia. But I was in Oia to catch the perfect sunset view from there. Oia is a very pretty town compared to Fira... I truly enjoyed spending time there.

Oh just to add, I was there in May, and I thought it was perfect. The weather was warm but not too scorching hot. And even in May it was already crowded, so I can't imagine July/August. I would suggest May or mid to late September if you want to avoid the island being too crowded.

Hi guys,

Thank you all so much for replying. It seems OIA is definitely the place to stay. As to Paros/Naxos, I heard other people mention it and will make sure to check it out. Thank you again.

Hi, to add my 2 cents worth - definitely Oia - the main town, Fira, is usually overrun with cruiseship tourists and is rather unattractive compared to Oia which is just lovely. We stayed there for 2 nights which is enough in my opinion and then went on to stay on Naxos which we also enjoyed very much. Tip: If you hire a motorbike to tour around the island, do take out puncture insurance! We were so glad we opted to take the insurance as we got half way round the island when the inevitable happened so we just called them up and they came and fixed it at no cost! We had to wait a while, but who cares? You're on Greek time!

Another vote for Oia. Just be prepared for the crowds at sunset.
Make sure you visit Amoudi (sp?) Bay, which is accessed by a long set of stairs at the end of town in Oia. It is home to several wonderful seafood restaurants on the water. And you can also swim off the rocks there.