Of around 6,000 islands in Greece, 227 are inhabited—so, yes, there are less crowded islands to explore. In the 1950s, some 180,000 people in total visited Greece each year—today, Santorini has more than two million visitors a year.
But Santorini still casts a mythic spell. The caldera view and looking at the depths of what the earth’s fire created somehow makes you question why we are here more than an average day does. The answer is impossible but at least one reason is clear: the wonder of these heart-stirring views–and feeling totally alive exploring one of the world’s great, iconic travel destinations.
Armed with recommendations from Town & Country’s editor in chief and Greece expert, Stellene Volandes, and my own research, I arrived in Santorini just as the season was kicking off with my family, including a four-year-old. I was warned that Santorini isn’t for children. In many ways, it isn’t. It’s a deeply romantic place with private plunge pools galore. It is a place meant for long seafood dinners and continuously refilled glasses of local wine—there are around 20 wineries on the island, including the wonderful Domaine Sigalas.
But it isn’t the forewarned danger deathtrap for kids—the cliffside stairways are near vertical, but they aren’t usually close enough to the edge to worry. In fact, there were a lot of things for kids to love—adorable macaroon and ice cream necklaces, friendly and watchful cats, afternoon gelato, the black sand beach. The Canaves Oia brand has a relatively new family-friendly property, Canaves Epitome—with plenty of pool time, balloons delivered to the room and staff passing out art supplies.
For any visitor to Santorini, meals center around salads with chunky cucumbers and tomatoes with a slab of feta on top and pungent oregano, grilled meat and the freshest seafood, koulouri (Greek sesame bagels), thick yogurt with cinnamon and honey, and for a casual option, souvlaki or a stuffed gyro. (See below for my favorite find, where dinner cost a total of 26 euros).
We hired a driver through the hotel to take us around the island—there is not a traffic light or roundabout to be found anywhere on the island. The day out included a walk up to the top in Pyrgos for the highest viewpoint on the island; a short stop for wandering and coffee in Fira (the shops here are more focused on keychains and postcards); and a new beach bar discovery on Perissa Beach, a black sand beach. Driving around the island, you see fields of cherry tomatoes and grapes that look like lettuce baskets—they are grown close to the ground in little circles so the wind doesn’t knock the vines down.
Many Santorini favorites remain. Anyone going likely has received a recommendation for Metaxi Mas—and it is worth it for casual Greek taverna fare with a breezy view of the center of the island. Some, like Katina’s fish tavern, have closed. After a long lunch at one of the taverns in Ammoudi Bay (my pick below), it’s worth the 300-step uneven climb from Ammoudi to Oia. Just wear good shoes and look down for donkey dung.
Another option for a day is to take the several hours-long walk from Oia to Fira for phenomenal views.
Below, some news and finds from my recent trip, mostly centered around Oia, where I stayed.
Staying in a luxury cave suite is now commonplace on Santorini, but in 1983, Markos Chaidemenos’ parents turned three inherited caves into a hotel and the Canaves Oia brand started a trend—and the first of what is now five properties on Santorini.
The flagship is Canaves Oia Suites, showcasing the now-iconic Santorini color scheme—airy and white complemented by varied blue of the pools and the caldera. For larger multi-gen families or celebrations, the eight-suite Sunday Suites is often bought out, but their top-floor restaurant, Veranda, is the best place for a 360-degree view, aperitivo and dinner away from the crowds as the sun sets.
For families with young children, Canaves Epitome is the newest in the portfolio, after Markos and his family took a “very big bet” when buying the land in 2015, on the “sunset” part of the island above Ammoudi Bay. “It is a design we could never do on the cliffs,” Markos says. “A proper five-star family resort with a lot of timber, cacti, stonework and natural materials that are heavy to carry. We wanted to make a small oasis outside of the village of Oia with access to Oia. It’s called Epitome, but we think perhaps we should have called it Sanctuary—people like this sanctuary.”
The big news is that the Canaves Oia brand is expanding beyond Oia—the family have significant hotel projects in the works on two other Greek islands. (Not Mykonos.)
Until I was five years old, I lived full time in Santorini. I was raised in Athens, but spent all my summers and Easters in Santorini. At 18, I left for hotel school in Switzerland, came back at 22 and then took over as general manager at 23—was too young. Today, my [new wife and I] live here full-time when the hotels are open.
Do you have a favorite activity you suggest to visitors? We have the catamarans [the family also owns around 25 yachts and catamarans with Sunset Oia], so I’d definitely suggest a boat day out. It was my father’s hobby and hence my hobby—because of that, we decided to invest in this activity and turn our second passion into a business, as well.
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities.Get In Touch