Sometime around 1600 B.C., the southern Aegean Sea was the site of one of the largest volcanic eruptions in recorded history. As ancient Thera ejected nearly 24 cubic miles of ash and debris, the sea flooded into the caldera of the collapsed island volcano, forming a great bay more than 1,300 feet deep. But towering above the water’s surface, portions of the volcanic rim remained—including a small crescent of rock that would become one of the most beloved islands in Greece.

To this day, the great volcano that formed Santorini continues to smolder beneath the sea. Yet a series of earthquakes and smaller eruptions in the modern era have failed to dislodge the beautiful villages that now adorn the volcanic rim. The crown jewel among them is the island’s northernmost town of Oia (pronounced EE-a), where a collection of stucco cave homes and blue domed churches cling to the hillside a thousand feet above the caldera. But such extraordinary beauty is not without its price. As more than one million visitors converge on Santorini each year, the island’s narrow walkways become nearly impassable in summer—while daily cruise ship crowds quickly overwhelm the scant remains of true Greek character.

So do yourself a favor and peruse the VRBO rentals in shoulder season. You’ll have Oia (almost) all to yourself for the next three days.

FRIDAY

The Book Thief

On July 9, 1956, a 7.8 magnitude earthquake shook the southern Cyclades, leaving 48 people dead, hundreds more injured, and nearly 2,000 homes in ruins on Santorini. In the disaster’s wake, Oia—once home to a powerful eastern Mediterranean merchant fleet—was nearly deserted, as many residents fled to Athens, Australia, and the United States. But in the decades since, Oia has slowly and carefully rebuilt in the traditional architectural style, and redeveloped itself as a picture-perfect resort town.

Begin your visit on Nikolaos Nomikou, the narrow pedestrian thoroughfare that acts as Oia’s spine. And although there are countless shops and staircases competing for your attention, allow at least an hour to get lost inside Atlantis Books. The brainchild of two young American vacationers, this cozy basement bookshop—and its carefully curated selection of novels, poetry, short stories, and biographies—is a little piece of heaven for English-speaking readers and writers. And thanks to the printing press in the back room, you can take home beautiful, unique editions of the staff’s favorite short works.

Before Sunset

You’ll know the sunset is almost upon you not from the time or the color of the sky, but from the crowd of sunset-gazers walking westward for Oia’s most spectacular show. Whether you scale a rooftop, climb the walls of the old Venetian castle, or share a patio table at Kastro with a bottle of rosé, be sure to secure a prime seat for Oia’s most beloved nightly tradition—oohing and ahhing at one of the most beautiful sunsets in the world.

Right Said Red

Although living on an active volcano is a risky endeavor, it isn’t without its benefits—including nutrient-rich soil that allows tomatoes, fava beans, and white skin eggplants to thrive. And few restaurants do better justice to the island’s ingredients than Red Bicycle, an elegant showcase of Mediterranean cuisine with a local twist. Housed in a cliffhanging mansion on Oia’s main drag, Red Bicycle’s terrace also lays claim to the best caldera views on the island (reservations essential).

SATURDAY

Fira And Loathing

Follow your nose this morning to the front door of Patisserie Melevio, where Oia’s best pastries, cakes, and traditional breakfast dishes await you just below street level. And be sure to eat hearty on the scenic back terrace—you have quite the day of hiking ahead of you.

Where Oia is tasteful and serene, the island’s capital city of Fira (roughly seven miles southeast) is busy and boisterous. Similarly situated on the edge of the caldera, Fira’s crowded streets overflow with restaurants, cafés, bars, and tourists—but today, it’s the endpoint of a truly spectacular hiking trail. With a picnic lunch and plenty of water packed, follow Nikolaos Nomikou to Oia’s southern edge, where you’ll meet up with the cliffside trail to Fira. And for the next three hours, as you walk through Imerovigli and Firostefani, you’ll enjoy some of the island’s very best panoramic views.

I Am 17, Going On 1800

As Oia reached the peak of its prosperity in the late 19th and early 20th centuries, merchant captains showed their affluence by building grand homes on the village’s highest points. One such mansion is now the lovingly restored home of 1800, a legendary standout in Santorini cuisine. Reserve a table in the charming roof garden, and you’ll be treated to an evening of incredible views and focused, intense local flavors—from roasted rooster with tomato puree to a perfectly sweet lemon tart (reservations essential).

SUNDAY

The Ammoudi Blues

Nearly a thousand feet below Oia, the tiny and picturesque port of Ammoudi rests where the caldera bay meets the open Aegean Sea. And on an island that boasts surprisingly few memorable beaches, Ammoudi is a gateway to one of Santorini’s loveliest swimming spots. All it takes is the will to descend nearly 300 stairs from Oia—and to disobey the signs warning of imminent rockslides—and you’ll be swimming in a sheltered blue cove, gazing at the cityscapes of Fira, Firostefani, and Imerovigli in the distance.

Before attempting the punishing hike back up the steps to Oia, gather your strength by dining on the freshest of fish at Taverna Katina at the water’s edge. Add a bottle of local wine to your lunch, and there’s no reason to leave before sunset.

Come On Selene

In 1986, Yiorgos and Evelyn Hatziyannakis opened the doors to Selene, an elegant showcase of the island’s flavors in the heart of Fira. But in 2010, Selene made a new home amidst the farms and vineyards of Pyrgos, a quiet hilltop village that offers a rare, authentic glimpse of old Santorini. What hasn’t changed is Selene’s exemplary treatment of classic Greek flavors—from red wine-marinated rabbit to lamb with vine shoots—and its commitment to flawless service (reservations essential).

A Few Notes

I’m really not joking about traveling to Santorini in shoulder season. Consider making the voyage in May, June, September, or October, and you’ll escape both the suffocating heat and the frightening crowds of summer. Just remember that much of the island shuts down between November and April.

Santorini is easily reached from Athens, Mykonos, and many other islands in the Cyclades, and OpenSeas is a fantastic resource for ferry timetables and ticket sales. But high winds, especially in the shoulder months, can cause cancellations, so always remember the cardinal rule of Greek ferry travel: be flexible.

Photographs

TITLE: The town of Oia | FRIDAY: The flooded caldera of ancient Thera; the town of Oia; the terrace of a VRBO rental home; a crowd gathers to watch the sunset | SATURDAY: Early morning in Oia; the view of Oia from the trail to Fira; the trail to Fira; a marker on the trail | SUNDAY: The staircase to Ammoudi; Oia dangles over the port of Ammoudi; swimmers in Ammoudi; a late afternoon meal in Ammoudi.