The Cliffside Suites of Santorini, Reviewed

There is a particular sound a Santorini morning makes from a caldera terrace: a ferry horn far below, a broom on whitewashed stone somewhere nearby, the clink of a coffee cup set down on a ledge that drops a thousand feet to the sea. I heard it four mornings in a row, from four different hotels, on a trip my friend Dana and I half-jokingly called “research.”

The idea was simple. Everyone who plans a splurge in Santorini faces the same question: which village, which kind of suite, and is the famous view really worth $600 or more a night? So we booked one night each in four very different cliffside hotels along the caldera rim, from a carved cave suite in Oia to a big, glossy resort near Fira, and kept honest notes.

Three of them were worth the money. One was not. I am not naming the properties here, partly because hotels change owners and managers faster than blog posts get updated, and partly because the lessons apply to dozens of similar places. Use these as a guide to what to look for, not a shopping list.

In this story9 sections

1. First, the geography that decides everything
2. Night one: a cave suite in Oia
3. Night two: plunge pools in Imerovigli
4. Night three: a quiet boutique stay in Firostefani
5. Night four: the one that was not worth it
6. Our picks, if you only get one stay
7. Where I’d stay again
8. Getting there and timing your stay
9. Santorini

First, the geography that decides everything

Santorini is the rim of a flooded volcano. The villages along the western edge, from Fira north through Firostefani and Imerovigli to Oia, hang over the caldera and face west toward the sunset. That is where every hotel with a view is, and every price on this page reflects that.

• Oia is the postcard: blue domes, windmills and enormous sunset crowds. Gorgeous, busy and the most expensive.
• Imerovigli sits at the highest point of the rim, looking at Skaros Rock. Quieter and, I think, the best views on the island.
• Firostefani is a 15-minute walk from Fira, with village calm and city convenience.
• Fira is the main town: lively, practical and a little loud at night.

Night one: a cave suite in Oia

Many traditional Santorini homes were dug into the soft volcanic rock, and the best Oia hotels have turned them into suites with vaulted white ceilings that stay cool all afternoon. Ours had a carved bedroom, a small sitting room and a private terrace with a heated plunge pool facing west. It cost about $780 a night in late September.

The first hour there was pure magic. The terrace was ours, the sea glittered below, and at sunset we watched the crowds pack the castle ruins in the distance while we sat in the pool with a glass of local Assyrtiko. That privacy is the real luxury in Oia. Without it, sunset here can feel like a stadium.

The downsides: about 150 steps down from the nearest lane, the room was a little damp at night, as cave rooms can be, and breakfast was slow. Still, it was the most memorable night of the four.

Night two: plunge pools in Imerovigli

This was my favorite, and also the one I would book again with my own money. A small, modern hotel with around fifteen suites cascading down the cliff, each with its own plunge pool, all facing Skaros Rock and the open caldera. We paid about $520.

What made it great were the details. A staff member carried our bags down the steps without being asked. Breakfast arrived on our terrace at the exact time we chose, and it was enormous: Greek yogurt with thyme honey, warm spinach pie, tomatoes that tasted like summer, and fresh orange juice. In the evening we walked out to Skaros Rock, about 45 minutes round trip, and then had dinner a few minutes up the lane.

The view is what you pay for. The privacy is what you remember.

Maya Collins

Night three: a quiet boutique stay in Firostefani

At about $340, this was the bargain of the trip, and it did not feel like a compromise. A family-run hotel with a dozen simple, bright rooms, a shared infinity pool and a terrace facing the volcano. No private plunge pool, but we barely noticed: at 10 a.m. we had the shared pool to ourselves, and the owner’s mother left a plate of homemade cookies outside our door.

Firostefani also has the practical advantage of being flat-ish and close to Fira, so restaurants, taxis and the bus station are all a short walk away. The famous cliffside path from Fira to Oia passes just above the hotel. We walked part of it before breakfast, while the light was soft and the path was empty.

Night four: the one that was not worth it

The last hotel was a large resort below Fira, with over a hundred rooms, a spectacular infinity pool and a very glossy website. We paid about $610 for a “caldera view junior suite,” and the view turned out to be partial and mostly of the next building’s roof. The hot tub on our shared terrace sat in full view of three other suites. The pool was lovely but crowded by 9 a.m., and the music from a nearby bar carried well past midnight.

Nothing was terrible. It was simply ordinary, at a price where ordinary stings. The lesson: in Santorini, a big hotel with a grand pool rarely beats a small one with a private terrace.

Our picks, if you only get one stay

Getting there and timing your stay

There are no nonstop flights from the US to Santorini. The easiest route is a nonstop to Athens from New York, Newark, Philadelphia, Atlanta or Chicago (seasonal routes vary), then a 45-minute flight to the island. Ferries from Athens’ port at Piraeus take about five to eight hours, depending on the boat. US citizens can visit Greece without a visa for up to 90 days within the Schengen area; check before you fly whether the EU’s new ETIAS travel authorization has started applying to American travelers.

The season runs from about April to October. July and August bring heat, cruise crowds and peak prices. We went in the last week of September: water warm enough to swim, sunsets around 7:15 p.m., and room rates noticeably lower than in summer. Most caldera hotels close from November to March.

If I had to choose just one, I would spend two nights in Imerovigli and walk to Oia for an afternoon. But honestly, the best caldera hotel is the one where you put your phone down, sit on the terrace with a coffee, and let the island do what it has done for centuries: stop you in your tracks.