Pick one caldera village as the overnight. Moving hotel every night kills the point of a cave room and a view you have already paid for.
Oia
The postcard: blue domes, caldera drop, boutique hotels, and sunset crowds. Stay here if the photo is the trip. Eat elsewhere at dusk if you dislike queues, or book a terrace. The village is small; you will walk the same lane twice, which is fine at 8am and grim at 19:00 in August.
Fira and Imerovigli
Fira for buses, the cable car to the old port, shops, and a livelier evening. Imerovigli for the same caldera with fewer shops and a higher rim. Many repeat visitors sleep in Imerovigli and day-trip Oia in the morning, before the tenders arrive.
Beaches, Pyrgos and Akrotiri
Kamari or Perissa for a swim day on black sand. Pyrgos inland is the quieter stone village if the caldera feels finished — a hilltop with views and fewer blue-dome selfies. Akrotiri combines the Bronze Age site with Red Beach nearby. One beach day is enough; Santorini is not a sand-and-club island in the Mykonos sense.
Ports and the airport
Athinios is the ferry port, a steep bus or taxi ride below Fira. The airport (JTR) is on the island’s flatter east. Neither is a place to stay. Land, go to your village, and unpack once.
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