A little local perspective
Worth knowing.
Worth going.
- Destination
- Santorini, Greece
- The selection
- 13 hotels
- Your kind of trip
- honeymoon · couples · views · special occasion
$$$ to $$$$ — roughly 400-1,500 euros a night, closed much of the winter
The Oia sunset has become a logistical event. From about six in the evening the lanes leading to the castle ruins fill with people walking in one direction, the viewing points are three or four deep by seven, and photographs of the crowd watching the sunset now outnumber photographs of the sunset. It happens every night from May to October.
The caldera itself is worth every bit of the reputation. Santorini is the rim of a volcano that erupted catastrophically around 1600 BC, leaving a flooded crater three hundred metres deep with a cliff wall on its eastern side. The villages sit on top of that wall. The view is straight down and straight west.
Why a private terrace is the entire product
Almost every hotel on the caldera edge is built the same way: rooms cut into the cliff in layers, each with a terrace on the roof of the one below. That arrangement is what produces the private, unoverlooked, west-facing outdoor space with a plunge pool, and it is why Santorini hotels cost what they do.
Get one and the sunset happens where you are standing, with a drink, and you never go near the Oia lanes at six in the evening. Book a room without one, or with a terrace overlooked from above, and you join the crowd.
The three caldera villages differ. Oia at the northern tip has the best sunset angle and the worst crowds. Imerovigli sits at the highest point of the rim, has fewer visitors and arguably a better view along the caldera. Fira is the capital, busiest by day, best connected and cheapest.
The thirteen below are grouped by village, with two off the caldera at the end.
Oia
The northern tip. The classic view, the highest prices and the crowds.
Katikies Hotel is the original cliff hotel in Oia, with an infinity pool that appears in most photographs of the island and terraces stepping down the rock. It set the pattern everything else follows.
Canaves Oia Suites occupies a set of cave houses with private plunge pools, a serious restaurant and the most consistent service in Oia.
Canaves Oia Epitome is the larger, newer sister property slightly outside the village with more space, a bigger pool and a shuttle into Oia. It is the better choice for a longer stay.
Andronis Luxury Suites sits on the cliff with suites cut deep into the rock, private pools and a position at the quieter end of the village.
Perivolas occupies a group of whitewashed houses at the tip with a pool carved from the volcanic rock, no signage and a deliberately austere aesthetic. It is the most restrained hotel on the island.
Imerovigli and Firostefani
The highest part of the rim, between Oia and Fira. Quieter, with a longer view down the caldera and the Skaros rock below.
Mystique, a Luxury Collection Hotel sits on the cliff at Imerovigli with sculptural white architecture, private terraces and the most photographed pool on the island after Oia's.
Grace Hotel Santorini occupies a position on the rim with a spa, a large infinity pool and the best food of the caldera hotels.
Astra Suites sits at Imerovigli with terraces stepping down the cliff, plunge pools and a family operation going back decades. It is the value pick on this stretch.
Cavo Tagoo Santorini occupies a cliff site with contemporary design, a long infinity pool and the widest caldera outlook of the group.
Fira and Firostefani
The capital. Busiest, best connected, and the cheapest way onto the caldera.
Aressana Spa Hotel and Suites sits on the cliff below Fira with a pool, terraces and the shortest walk to the town's restaurants and the cable car.
Cosmopolitan Suites occupies a position on the rim at Firostefani with suites, private pools and a quieter setting ten minutes' walk from Fira.
Off the caldera
The eastern and southern side of the island: black sand beaches, vineyards, no cliff and much lower prices.
Vedema, a Luxury Collection Resort occupies a fifteenth-century village estate inland at Megalochori with a large pool, a wine cellar in the old cistern and considerably more space than any cliff hotel. There is no caldera view and that is the trade.
Istoria sits on the black sand at Perissa with a pool, a good restaurant and a design-led interior. It is the beach alternative and the best value on the island.
What we have left off
The cave suites in Oia without a private terrace are excluded, and many of them are beautiful inside. If the terrace is shared or overlooked from the path above, you have bought the room and not the reason for it.
What to do
Watch the sunset from your own terrace. If you are not on the caldera, go to Imerovigli or the Akrotiri lighthouse instead of Oia.
Akrotiri is the Bronze Age town buried by the eruption and preserved under ash, and it is far more impressive than most visitors expect. Go early.
Walk the caldera path from Fira to Oia. It is about ten kilometres along the rim, takes three to four hours, and is the best thing on the island. Start at seven.
Do a wine tasting. Santorini's vines are grown in baskets on the ground against the wind and the assyrtiko is unlike anything else.
Take a boat to the volcano and the hot springs, or better, hire a small boat around the caldera in the late afternoon.
Practical notes
The airport and the ferry port both connect to the villages by road; transfers from the port at Athinios are on a steep switchback and take 25 to 40 minutes.
May, June, September and early October are ideal. July and August are hot, extremely crowded and at peak rates. The island largely closes from November to March.
Cruise ships arrive most days in season and concentrate in Fira between about ten and five. The caldera path and the villages are calmest before nine and after seven.
Luggage and steps are a real issue. Most cliff hotels involve a lot of stairs and porters carry bags down; confirm access if that matters.
Explore 4 & 5 Star Santorini Hotels
Prices shown are sample rates from upcoming dates — not quotes for specific dates. Open a hotel and choose your own dates and guests to see the exact price.
Questions people actually ask
Is Oia worth staying in?
For the view, yes. For the crowds, it is the busiest village on the island. Imerovigli gives you most of the view with a fraction of the people.
Do you need a private pool?
A private terrace, yes. A plunge pool is a bonus rather than the point.
Is Santorini overrated?
The caldera is not. The experience of Oia at sunset in August is. Time it right and it remains extraordinary.
How many nights?
Four. Three on the caldera and one elsewhere works well, or pair it with another island.
