How to Avoid the Crowds on Santorini, the Island That Launched a Thousand Selfies

One morning at the end of last summer, I found myself, very briefly, to be the sole custodian of the world’s most beautiful view. I was on the Greek island of Santorini, and had stumbled upon the rooftop terrace at the wonderful Atlantis Books in the town of Oia — pronounced ee-ya, like a gasp of wonder. I found an alfresco reading desk and an empty chair, where I sat for a moment and gazed out, alone and unimpeded, at the vast, sunken heart of the island’s caldera. There were those famous volcanic cliffs, the whitewashed houses, and the occasional blue dome of an Orthodox church, all framed by a perfect azure sky and sea.

Santorini is known as the most photogenic place in the Cyclades — the archipelago that spirals through the unearthly waters of the Aegean Sea, southeast of the Greek mainland. It owes its striking looks to a freak geological occurrence. More than 3,500 years ago, a huge volcanic eruption collapsed the center of what was then a much larger island, allowing the sea to fill its interior. The result of this explosion, thought by some to have inspired the myth of Atlantis, is a vast oceanic amphitheater — and one of the most dramatic landscapes in all of Greece.

With its vertiginous location above the caldera, Oia offers the best views. Which is why, in the hours before sunset (even in October, when I visited) the town takes on the feverish atmosphere of a Black Friday sale. Increasingly frantic people perch on terraces and jostle for the best angle on the setting sun. There was a greater likelihood of losing an eye to a selfie stick than having a transcendent encounter with the island’s natural beauty. Even in the daytime, Oia sometimes felt like it was bursting at the seams. Within seconds of sitting down on the tiny rooftop at Atlantis Books, I had my view blocked variously by a woman from Nanjing in a bridal gown posing for her pre-wedding photos, a Spanish couple celebrating 45 years of marriage, three Korean women, five Canadians, and a man with a tattoo of Hannibal Lecter on his head.

Tourism on Santorini took off in the 1960s, but since the advent of social media, the industry has been turbocharged by a critical mass of Instagram posts, bucket-list blogs, and listicles about the best sunsets on earth. Around 2 million people now visit the island each year, lured by those images of an orange sun dipping into the sea behind Oia’s iconic windmills. Even if you’ve never been there, you know what it’s supposed to look like. It’s the famous Greek beauty that launched a thousand screen savers.

I wanted to see if it was still possible to have an authentic experience on Santorini — and if not, to see if there were islands in the Cyclades where I might find one. After all, the entire archipelago is known for that striking combination of piercingly blue water, traditional whitewashed buildings, and rugged landscapes that Santorini has done so much to popularize. An hour away by jet boat, tiny Folegandros offers similarly dramatic vistas in an atmosphere of rustic calm; Milos, once the resting place of the Venus de Milo, an icon of classical beauty, has extraordinary beaches, archaeological sites, and a timeless, peaceful interior. Was there a way, I wondered, to still experience Santorini, and the rest of this region, in all its raw, unspoiled glory?

I was shown around the island by Nikos Boutsinis, the affable, bearded proprietor of Santorini Walking Tours. Nikos, who has the rangy physique of a distance runner, whisked me through the heart of Oia to avoid a boatload of visitors about to be discharged from one of the cruise ships anchored in the bay. “The cruise-ship visits define how much fun we can have,” he said. “We must go quickly.” On our way out of town, he pointed out the ornate captain’s houses, built with the spoils of the island’s 19th-century shipping boom, and took me inside dwellings that had been carved from the volcanic rock of the cliffs. Then we jumped into his car and headed inland.

Before the arrival of mass tourism, Santorini’s vineyards were one of its main sources of income, and today much of its interior is still given over to grape cultivation. As we drove toward the town of Vourvoulos, near the island’s quieter eastern shore, Nikos pointed out the vines, which had been trained into distinctive low basket shapes to protect them from the Cyclades’ famous winds. At Vassaltis Vineyards, we tasted whites made from the local grape, Assyrtiko, which the island is famous for. To anyone whose idea of Greek wine has been defined by the overpowering pine flavor of retsina, Assyrtiko — which produces magnificent, complex whites with hints of honey and green apple — is a revelation. At the Artspace winery in Exo Gonia, our next stop, we sampled vinsanto, a dessert wine made from sun-dried Assyrtiko grapes. It was sweet but not cloying, with a heady scent like attar of roses.

Just outside Exo Gonia, Nikos showed me a group of derelict houses that have stood empty since 1956, when the most recent earthquake hit the island. The event caused colossal damage, destroying more than half the buildings in Oia and Fira and setting off a wave of emigration. The island’s future looked bleak until the influx of visitors began to transform its fortunes. Tourism is now by far the most important industry on the island — and is growing exponentially. Nikos, like other young islanders I met, sees it as a mixed blessing: he’s happy to be able to share the island’s beauty, but less enthusiastic about the soaring rents and crowded roads.

There are undeniable upsides to Santorini’s global fame. Direct flights, for one, and a disproportionate number of exceptional places to stay (the 30-square-mile island is home to more than 280 hotels.) I wallowed in luxury at Canaves Oia Epitome, where my fellow guests were mostly blissed-out honeymooners enjoying private ocean views from the property’s brand-new, minimalist suites — each of which has a private plunge pool framed by citrus trees.

Food on Santorini runs a gamut of dining experiences far broader than on the typical Greek island, with everything from fine dining to farm-to-table food on offer (the island even has a McDonald’s). After the sunset crowds had died away, I visited Vineyart in Oia, a fresh, airy space where the young, enthusiastic owners offer delicacies from across the Cyclades, including spectacular charcuterie, cheeses, and flights of local wine. And I ate an extraordinary meal at Canaves Oia Epitome’s Elements restaurant, where head chef Tasos Stefatos is clearly bidding for the island’s first Michelin star with a tasting menu filled with witty nods to Santorini’s geology: red mullet blackened with powdered squid ink that resembles ash; a molten chocolate volcano.

On my last day, I booked a boat trip around the island — one of the best ways to get a clearer sense of Santorini’s unusual topography and to access some of its less crowded black volcanic-sand beaches. As sunset approached, our skipper jockeyed for position with 20 other catamarans, angling for the best view. Behind us, I could see thousands of visitors on the cliffs at Oia, the flashes of their camera phones sparkling away as they rehearsed for the unmissable Instagram moment ahead. But five minutes before sunset, the sun slipped behind a bank of clouds, like a diva who’d decided to refuse the crowd an encore. I could almost feel the disappointment emanating from the cliffs. Then suddenly, the sun emerged, plunging spectacularly into the sea, leaving a trail of cotton-candy pink and powder blue clouds in its wake.

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Though it is just an hour away by jet boat, Folegandros feels like Santorini’s polar opposite: quiet, understated, almost timeless. The island is tiny — with a population of less than 800 — yet despite its small scale, the landscape is big on drama. Like the other islands in the archipelago, Folegandros is a partially submerged mountain, whose sheer northern side plunges straight into the sea. From the Church of Panagia, or the Virgin Mary, which sits at the top of a strenuous switchbacked path above the tiny capital, Chora, you can take in most of the island. It stretches out in a narrow finger to the west, the traces of abandoned farming terraces still visible on its arid flanks, and forms a distinctive hourglass shape that is pinched, in the middle, to a width of just a few hundred yards.

From this lookout, the village of Chora seemed absurdly small, yet at night, its tiny alleys became mazelike. One evening I got quite lost in its backstreets after enjoying a negroni under the bougainvillea of a local bar. It took me a few moments to realize that all I needed to do to reorient myself was look up at the Church of Panagia on the hillside above the town. Once I did that, I quickly found my way back to the trio of tree-shaded central squares, where locals and tourists chatted over fragrant plates of souvlaki and bottles of Mythos beer.

Folegandros is so small that I was able to drive its entire length in about 15 minutes in my rental car. The farther I got from Chora, the more the 21st century seemed to slip away. I passed farmers riding donkeys or using them to carry precious water to their crops. When an islander talked to me about the changes brought on by the industrial revolution, he wasn’t talking about the 1820s, but rather the electrification that arrived in 1974. Sitting on my balcony one evening, I watched as a single pair of headlights traveled the length of the island’s main road and vanished, plunging the scene back into a deep, arcadian silence.

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I arrived on Milos at the end of the summer season, on the tail of a Mediterranean cyclone. So unusual was this event in Greece that it had given rise to a new portmanteau: medicane. But despite dire warnings, the storm, christened Zorba, had left Milos unscathed. The only obvious effect was that the startling colors of the water — turquoise, lapis, periwinkle — had taken on a milky hue.

I was staying at Milos Breeze, an elegant, understated boutique hotel overlooking the tiny village of Pollonia, on the island’s northeastern tip. Through the wooden shutters of my whitewashed room, I could hear waves, stirred up by the storm, breaking on the nearby shore. The hotel’s co-owner, Dimitris Vamvakaris, warned me that Milos’s charms were not as overt as those of its more famous neighbor. It took a bit of effort to get to know the place. “You don’t have everything in front of you,” he said. “You have to explore the island.”

Mindful of Dimitris’s warning, I met up the next morning with Alexandros Kiziriadis, a local guide. Originally from Athens, Alexandros fell for Milos when he spent his honeymoon on the island in 1978. Now a handsome man in his sixties, with swept-back curly gray locks, Alexandros is still happily married, and his love for Milos remains not only passionate but monogamous: he could barely bring himself to admit any other island was worth visiting at all. “Eh,” he said, when I mentioned any other part of the Cyclades. “It’s not the best.”

Much of the western half of Milos now falls under an environmental initiative called Natura 2000, a Europe-wide conservation project begun in 1992 that protects the continent’s most beautiful spaces. This wild, undeveloped part of the island is accessible only by four-wheel drive. Alexandros drove us out west on unpaved roads, through a landscape of tiny one-room chapels, goats, and lone farmsteads. Ten miles down a twisting dirt road we came to an empty beach called Ammoudaraki. Over a picnic lunch, Alexandros tried — unsuccessfully — to teach me the Greek alphabet. “This one is i,” he said. “This one is also i. This one is o; this one is o. This one and this one together make i.”

Ammoudaraki is my platonic ideal of a beach: beside the crystalline blue water is a fringe of pale sand lined with myrtle bushes. A hundred yards offshore, the tiny, sphinx-shaped island of Antimilos rises up from the translucent water. Even in the height of summer, Alexandros assured me, the beach is too remote ever to become crowded. “Milos has over a hundred beaches. Eighty are easy to find. Twenty are only accessible by boat.” The result of the island’s volcanic geology, Milos’s beaches are indeed remarkable, the interactions of fire, stone, and water evident in an amazing range of caves, cliffs, sand, shingle, and luminous white stone.

We visited Papafragas, on the northern shore, where the volcanic cliffs are shot through with several caves and arches — giving them, from a distance, the look of Swiss cheese. Alexandros showed me a place where pale green water, still a little cloudy from the medicane, churned through one of the arches and filled a secret inlet. A couple of miles west along the coast at Sarakiniko beach, the sea collides with a dazzling white shore formed of volcanic perlite, gypsum, white lime, and chalk. The effect was ravishing: it had the elemental simplicity of a daring minimalist sculpture.

A 10-minute drive away, Alexandros and I stopped in Plaka, the beautifully preserved main town, where the streets are lined with flat-roofed whitewashed houses. At the Utopia Café, perched above the island’s huge bay, we ordered espresso. Not far from where we were sitting, Alexandros said as we sipped our coffee, the Venus de Milo was unearthed by a farmer in the 19th century. The famously beautiful (and armless) statue was whisked away to France and now stands in the Louvre.

Sitting in Utopia with Alexandros, I pondered which island had been my favorite. Below us sparkled the Aegean, across which Greek ships sailed for Troy in Homer’s Iliad. It struck me that perhaps the ancient statue of Milos carried a message. According to myth, the goddesses Aphrodite, Hera, and Athena took part in a beauty contest judged by the mortal Paris. Paris declared Aphrodite the victor, but his decision caused such acrimony that it set off a series of events that led to the Trojan War. As Alexandros and I finished our coffee and headed out into the sunshine I realized, smiling, that the lesson of Greek myth is not to pick a winner.

Island-Hopping in the Cyclades

You’ll want at least a week to combine the glamour of Santorini with the unspoiled beaches and villages of Milos and Folegandros.

Getting There

In the summertime, multiple carriers offer nonstop flights to Athens from Chicago, Philadelphia, Newark, and New York City. From the Greek capital, fly to Milos or Santorini, where you can transfer between the islands by boat. Or take a ferry from Piraeus, the port of Athens — the fastest jet boats reach Milos in just under three hours, Folegandros in four hours, and Santorini in less than five. Rental cars are easy to arrange on all three islands.

Santorini

There’s no shortage of high-end hotels on Santorini — though you’ll need to book well in advance. I stayed at Canaves Oia Epitome, where each of the 24 suites and villas has its own private pool with Aegean views. Perivolas is a classic property set into the cliffs outside Oia, while the new Istoria brings a boutique aesthetic to the low-key Perivolos beach. At Vineyart, in Oia, updated regional dishes made with locally sourced ingredients are paired with wines made on the island. The picturesque Aktaion, meanwhile, has been serving classic Cycladic cuisine since 1922. I spent a day with Santorini Walking Tours, a great way to see the islands’ hidden treasures, such as wineries, archaeological sites, and unspoiled inland villages.

Milos

The stylish Milos Breeze is a boutique hotel with a mineral-rich swimming pool and stunning views. Milos Cove is a new resort with chic, minimalist rooms and suites set on a cliff above a gorgeous stretch of shore.

Folegandros

I loved my stay at Anemomilos, a delightful hotel on the cliffs outside the little town of Chora. The family-run Pounta serves classic Greek food in a bougainvillea-draped courtyard.

Tour Operator

My trip was set up by Christos Stergiou, a member of the A-List — Travel + Leisure’s list of top travel advisors. His company, TrueTrips, can arrange customized itineraries in the Cyclades with all flights, ferries, and ground transfers included.