THE TRIP
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The short answer
At a glance
Oia in the late light, when the day-trippers have gone back down to the port.
I stayed at Charisma Hotel in Oia in September 2022, and the picks below are the hotels I place clients in now. Santorini is the rim of a volcano that blew its own centre out, which is why the villages hang off the cliff and why the light at seven in the evening is unlike anywhere else I photograph. It is also why where you sleep matters more here than on most islands: the caldera villages are vertical, the beaches are on the other side, and the day-trip crowds land in one place. So I think about it by village, and I will say up front that my favourite piece of advice is to split your stay. Two or three nights on the cliff for the view you came for, then move inland or to the coast and watch the island change completely.
Seven in the morning on the cliff, before the heat, with the shutters open to the volcano.
Breakfast arrives on the terrace; nobody goes down to a dining room here.
Grace Hotel, Auberge Resorts Collection · Imerovigli · from $700 a night
Imerovigli is the most beautiful stretch of the caldera and the calmest at night, which is why it is where I most often put honeymooners, and Grace is the standout: the only hotel on the island holding two MICHELIN Keys. It runs April to October, takes no guests under fourteen, and has Lefteris Lazarou’s Varoulko Santorini downstairs, so dinner is a flight of stairs away. Ask for a suite with its own plunge pool facing the volcano; my clients typically enjoy breakfast and an upgrade where they apply.
Andronis Concept · Imerovigli · from $700 a night
Twenty-eight rooms and one Key, beautifully done, and the quieter sister to the Andronis addresses in Oia. For a couple who want the Imerovigli calm without the Grace price, this is the one I book. Between Lycabettus and Lauda the group holds three MICHELIN stars across two restaurants, which no Greek hotel group has ever done, and both are a short drive away.
Canaves Epitome · Oia · from $700 a night
Oia is busiest by day and loveliest in the evening, and most of the island’s best addresses are here. Canaves has four properties in the village; Epitome holds a Key and is the one I book most. Note the names have changed, so the old Canaves Oia Epitome you may have bookmarked is now simply Canaves Epitome.
Perivolas · Oia · from $700 a night
The independent one I have the softest spot for, still family-run on the cliff edge, with a hideaway villa over on Therasia that you can only reach by sea. Honestly, if you want the Oia of the photographs without a brand attached, this is it.
Charisma Hotel · Oia · from $700 a night
This is where I stayed in September 2022, and where most of my own Santorini photographs were made, on the Oia cliff in that seven o’clock light. It is the one I can describe from the inside rather than from a client’s report, and it is a lovely base for a first visit to Oia.
Mystique, a Luxury Collection Hotel · Oia · from $700 a night
All forty-two suites were redesigned for the 2025 season, so it reads newer than its years. Good for people who like a Marriott Bonvoy footprint behind a very Greek hotel.
Katikies Garden · Fira · from $700 a night
Fira is where everything is and where the day-trip pressure lands, so I book it for people who want life on the doorstep. Katikies Garden is the pick, partly because Selene, one of the island’s serious restaurants, is in its courtyard. If you want the same caldera view with a gentler walk into town and noticeably lower prices, look ten minutes along the cliff to Firostefani.
Istoria · Perivolos · from $700 a night
On the black sand at Perivolos, a Design Hotels member with a Key, and the one I recommend for people who actually want to swim. This is the second half of the split stay done properly.
Sandblu Santorini · Kamari · from $700 a night
New for 2026 and Hilton’s first LXR in Greece: sixty-six rooms on the black-sand beach at Kamari. I have not stayed yet, so this one is on my list to inspect, but it fills a gap the island has had for years.
A private villa with staff · the south · from $700 a night, by the week
For families and groups I will almost always look at a villa before a hotel. The caldera villages are charming for two people and hard work with a pram; a villa on the flatter south of the island with a cook changes the whole trip.
Vedema, a Luxury Collection Resort · Megalochori
Inland, inside an old winery in Megalochori, and expanded to seventy-four rooms for 2025. Nobody arrives in Santorini planning to sleep in a vineyard village, and then they do two nights here after the caldera and tell me it was the part of the trip they would repeat. The stone is cool, the evenings are quiet, and you are ten minutes from both the beaches and the cliff. If you take one thing from this shortlist, take the split: the cliff for the view, Vedema for the island.
Go late April to mid-June or September to mid-October, give it four nights minimum, five is better, and let me place you: the rates are the same as booking direct, with my perks wherever they apply, and I will ask for the room that faces the volcano. Read the Santorini travel guide for the rest of the island, what to know before you book, and the dossier for the practical side.
Asked often
Is it better to stay in Oia or Imerovigli?
Imerovigli if you want the quiet and the widest view of the caldera; it is where I most often put honeymooners. Oia if you want the evening: it is busiest by day and loveliest once the day-trippers leave.
Where should I stay in Santorini for the first time?
On the caldera for the first two or three nights, in Imerovigli or Oia, then somewhere on the black sand or inland for the rest. You see two different islands that way.
Can I have a caldera view and a beach at the same hotel?
Not really. The caldera villages hang off the cliff and the swimming beaches are on the other side of the island, which is exactly why I split the stay.
How many nights do I need in Santorini?
Four nights minimum, five is better, and late April to mid-June or September to mid-October if you can.
Is Firostefani a good place to stay?
Yes, for the same caldera view with a gentler walk into Fira and noticeably lower prices than Oia.
Where should families stay in Santorini?
I almost always look at a private villa with staff on the flatter south of the island before a hotel; the caldera villages are stepped and hard work with a pram.
The other Santorini: the south coast, where the swimming is and where I send people for the second half of the stay.