Thira & Oia
The caldera rim carries the view the islands are known for, with Fira as the busier main town and Oia at the northern tip for sunsets. Rooms here are cut into the cliff and reached by stepped lanes. The trade-off is swimming: the beaches sit on the far side of the island, so a caldera stay is a view holiday with beach trips, not a beach holiday.
Caldera views, sunsets and the classic Santorini stay.
Steps everywhere, and the swimming is down on the far coast.