Scenic Santorini: On the Trail from Fira to Oia

Blue-domed churches and white buildings on clifftop in sunset

I used to be fascinated with mythology as a child. The Greek pantheon, in particular, had always intrigued me with its tales of adventure and debauchery in faraway lands. Stories like Theseus and the Minotaur, the Birth of Aphrodite, and the Abduction of Ganymede untethered my attention from the ennui of school and homework. I dreamt often of these figures and of the vivid landscapes they inhabited; I dreamt that one day, I too, would traverse them on the way of my own adventure…

As the rays of a mid-October sun gradually filled the flooded caldera of Santorini, it’s easy to get carried away by the mythos of the islands. For as far as the eye could see, the waters of the Aegean stretched, until they seeped hazily into a cloudless, azure sky. With juts of rock and arid earth protruding from a blanket of Grecian blue and white, it was a morning ripe with lore and fantasy.

Cruise ship sailing past arid island

Legend has it that the archipelago of the Cyclades to which Santorini belongs was once a band of lively sea nymphs—the Oceanids. However, having fallen victims to the wrath of Poseidon, they were transformed into islands and eternally petrified.

Throughout history, Santorini has been given many names, such as Kallisti, ‘The Beautiful One’; and Strongili, ‘The Round One’. Following the Greek War of Independence against the Ottoman Empire, the island became officially known as Thira, although most people are better acquainted with its alias, a corruption of ‘Santa Irini’, or Saint Irene.

Left: man sitting on patio; Right: inside of a Cycladic-style room

The sound of clopping hooves and singing bells pull me back to the present. It was almost nine o’clock, and Fira, the island’s capital and most populous town, was just waking up. We bathed silently in the tranquil morning light, letting the whitewashed walls surround us with their most luminous and welcoming glow. Below our stucco terrace overlooking the caldera’s volcanic eye, the donkeys of Santorini were being led to their posts. Charged with portering visitors up and down the 600-odd steps between Fira and its old port, a long and arduous day lay ahead of them.

Left: Mediterranean-style breakfast; Right: smiling man on terrace overlooking ocean

Breakfast was served in contemporary style: omelettes with tomatoes and buttery Graviera cheese, freshly squeezed orange juice, and two pots of thick, creamy yogurt. Sébastien and I marveled at the idea that honeyed Greek yogurt may possibly be the closest thing to ‘ambrosia’, the food of the Olympian gods; and so we scraped up and savored every last bit. Hungry for another slice of heaven on earth, we prepared a rucksack with water and set out toward our destination: the glistening village of Oia, perched on the northern edge of moon-shaped Santorini.

Blue-domed church with three bells overlooking the sea

The trail from Fira to Oia passes through the island’s most beautiful villages and offers up some truly sensational scenery. Ten minutes by foot from the center of Fira, in the neighborhood of Firostefani (literally meaning ‘crown of Fira’), is the iconic Church of Saint Theodore with its three bells and large, sapphire dome.

Smiling man in sunglasses and shorts on a white balcony in front of high cliffs

Much like the other islands of the Cyclades, Santorini is known for its romantic atmosphere and adagio pace of life. However, it also has a dramatic flair, boasting unparalleled panoramas of alabastrine cave houses which cover the clifftops like thin sheets of snow.

Panoramic view of Aegean sea and triangle-shaped rock

From Firostefani, the path continues onwards through Imerovigli, a luxurious oasis bedecked by bougainvillea and infinity pools with sublime vistas of Skaros Rock, whence a small, long-gone city carved out of the mountainside sheltered its burghers from pirates and invaders in medieval times.

View of a caldera from clifftop

After Imerovigli, the road curves into a crescent, and a long, dusty trek through agrestic badlands awaits. What a wonder that amidst the ash and pumice, on the remote, skeletal rim of a sunken volcano, humanity has built an entire civilization. Here where few things grow, the people persevere.

White church at the entrance of village in late-afternoon light

The Church of Prophet Elias, one of many on the island with that name, greets wanderers at the end of the bend. Several hours later, with our knees tender and our foreheads damp with sweat, we arrived at last at the gates of Oia.

White stucco cave houses with bougainvillea and blue paint

Entering Oia is to transcend to another plane of beauty. Its juxtaposition of modern elegance and architectural heritage is perhaps the ideal example of a remote, exotic, and advanced utopia—an Atlantis above the water. On the main street of Nikolaou Nomikou, even the footpath sparkles and commands attention; paved with slabs of stone so polished and bright, a stroll down this gleaming avenue gives the illusion of walking on diamonds. Smaller alleyways hide their own charms and wind past some of the most picturesque spots to be found anywhere on the Cyclades.

Man in front of blue-domed church and open water at sunset

There on the cliffs of Oia, as the sun took its final bow, our day’s journey came to an end and a childhood dream was realized. Under a canopy of cinnabar and iris, we made our way out of the bejeweled city to the bus back to Fira.


Getting to Santorini

The quickest way to get to Santorini from Athens or abroad is by plane. Sky Express offers one-way flights from Athens to Santorini from around 90€.

Ferries also depart regularly to Santorini from Athens’ Piraeus port. Depending on the type of ferry, a one-way trip lasts from five to eight hours and costs between 40€ and 85€.

Where to stay

Tucked discreetly below the prime location of Fanari Restaurant, Fanari Vista Suites is a boutique hotel comprising four suites, all of which offer a private terrace with jacuzzi with full view of Santorini’s caldera.

Where to dine

Traditional dishes, fair prices, handsome waiters, and friendly service—Parea Tavern is the most convivial place to dine in Fira. The house also serves after every meal a complimentary glass of Vinsanto, Santorini’s hallmark sweet raisin wine.

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