Sorry for the late post. i wrote it this morning but Fodors crashed. I just posted it and see things have moved on nicely in the meantime.

Thanks again Stan,

We booked Hotel Glares. We have 2 of the 3 rooms on the third floor. I am now working on Santorini. Have you ever heard of oia sunset villas? one of them being swinging sunset? It looks nice for the price. I would love to stay up in one of the cave hotels but they really cost a ton. I think renting a villa might be the way to go instead.

You are going to love Glaros. WSe had two of the top floor rooms one visit as well. There is a big patio up there with a great view.

I don't know sunset villas. The pictures are really great. While it is not a true Caldera view it is high enough up to provide a pretty stunning vista.
It will be a bit of a trek into Oia for dining.
I suspect you are going to need a car.
One nice thing about being up there is you won't have to go to Oia and all the crowds for the sunsets.