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.
- If I had to recommend one restaurant experience on Santorini, I would choose Veranda Aperitivo Bar, with a 360-degree view of the island. Forget the sunset crowds at the tip of Oia overlooking Ammoudi Bay—and elbowing your way back after the sun sets. Here, the sunset is spectacular, the food is casual yet sophisticated, and you won’t want to be anywhere else.
- Sunset Tavern in Ammoudi is the most well-known option (and Katina’s has closed), but for a seaside table reservation, you need to plonk down a 160 euro holding fee for two people. You can also try going at lunch without a reservation—tables move quickly. But my vote is for Ammoudi Fish Tavern (10 euro per person holding fee)—the freshest seafood imaginable, a local fava dip made with raisins and shallots, lightly fried anchovies. If you don’t want a local whole fish or lobster, try the prawns saganaki with cherry tomato sauce, feta and grilled bruschetta.
- Omnia for seafood and pasta (and another amazing sunset view); Infinity Modern Bistro for Greek comfort food; fine dining at Petra and Elements—all at Canaves Oia hotels.
- Book a lunch at Forty One, a 40-minute drive from Oia right on the famous black sand beach, Perissa Beach. It is a former tomato sauce factory turned restaurant and cocktail bar—a breezy beachside restaurant with a large sushi menu.
- Best Casual Option: Pitagyros Traditional Grill House + Lolita’s Gelato. After a lengthy, fancy lunch, we wandered around Oia that evening, not wanting another long meal. We ran into tons of people gathering at Pitagyros and ordered pitas stuffed with chicken, tzatziki, onion, tomato and fried potatoes. Grab table seating outside if you can and settle in—it’s all made fresh so doesn’t come out quickly. Afterwards, Lolita’s Gelato is a three-minute walk away and the best on the island, made fresh daily.
- Love Me is a newer addition to Oia’s promenade, with a range of prices and showstopper summer bags from Omma and Greek fashion brands including La Châine by Fashionell and Twenty-29.
- Ammos has a tight edit for men and women—Ancient Greek sandals, evil eye necklaces, Missoni scarves and cover-ups and other brands: Beatrice .b, Chimi sunglasses, Maaji swimwear, The Motley Goat for sustainably produced pieces and Miss Bikini.
- Kisira, off the main promenade, fills a few spaces including pieces on display in the courtyard, but my favorite room had multiple colors of linen pants and bright linen kimonos to pull over.
- Minerali for the cutest macaroon and ice cream necklaces for children, handmade by one woman in Athens.
THE INDAGARE INTERVIEW
Santorini Local Markos Chaidemenos
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.)
How long have you lived or spent time in Santorini?
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.
- Absolutely Armeni restaurant. It’s so far away and off the beaten path and serves whatever is caught that day.
- I love Metaxi Mas, I love To Psaraki on the other side of the island, a very local fish tavern.
- Santorini is like a croissant, it used to be a round island and when half the island sank after the volcano, now it’s a complex of islands.
- Go to the island of Therasia, which you can see across from Oia. Go on a bike tour there and to the different villages. There are around 150-200 people living there and it’s like being in the 1960’s.
- Go scuba diving at St. Nicholas Church [Church of Agios Nikolaos]. Between the volcanoes is an old shipwreck and reefs.
- For jewelry, Poniros—the designer is a very good friend of mine.
- For clothes, Ammos and Kisira.