With those airline miles, if you value them about 1 penny each it is fairly easy to figure out where their use is most effective. I can't speak for the hotel points, but I'm sure there is some way of roughly "monetizing" them.

I agree with the other posters that the schedule is far too complex with too much time spent moving one's body, checking in, checking out, waiting for train/plane departure, getting to hotel from train/plane. Unless you are very young and very high energy and don't plan to do much sleeping.

Santorini has a gorgeous view, but I'm not sure how much there is to do there after you've looked at that for a while and wandered the shops? On the other hand, places like Rome are good for many days.

Romelle