When I looked at where to stay in Santorini, three areas came up: Oia, Imerovigli and Fira.  Between the three, I liked the hotel options in Fira (or “Thira”) the best.  Fira is relatively flat, there are plenty of restaurants and bars, and some incredible caldera views.  Geographically, it is closest to the port (I came on a ferry from Paros) and has views of Oia to the north as well as the center of the caldera.

Oia was very crowded even in the off season.  Expect crowds at sunset, as the tip of Santorini is known for some epic sunsets.