An Englishman, a Romanian, and a Maltese walk into a bar. This is not the start of a bad joke; it’s the start of a typical summer evening in Hermoupolis, the stately capital of Syros and all of the Cyclades islands. Sea and skyline blush hot pink as dusk settles over the rooftop bar-restaurant of the Aristide, a hotel in the aristocratic Vaporia neighborhood. The Englishman, a documentary filmmaker, has a summer house next door. The Romanian woman runs a yachting business on the island, and the Maltese gentleman works for the European Parliament but returns to Syros every summer. Aside from a shared love of this idiosyncratic island, what brought them together is their hostess, Oana Aristide.
With her tumbling curls and amusing banter, Oana is not your typical hotelier. Since moving to Syros on a wing and a prayer (she and her family had to take out a hefty loan to finance their fledgling hotel), she has come to know everyone and everything worth knowing on the island. There’s the optician whose ancestral home has a frescoed ballroom and candlelit chandeliers, the doctor with peacocks and an outdoor cinema on his rambling estate, and the real estate agent who, like many locals, is also an accomplished musician.
“During the 1800s, Syros was the wealthiest place in Greece, and the architecture shows it,” Oana told me. “It’s not a beach or party island. It’s an island of culture.” With a lively year-round scene bolstered by a community of civil servants and university students, tourism has never been more than a sideline. There was a plan to build an international airport, but it’s said that the people of Syros deliberately made the runway too short so charter flights couldn’t land. “This could be an urban myth,” Oana said, “but it’s plausible.”
Although nowhere near as busy as the neighboring islands of Mykonos and Páros, Syros is beginning to attract travelers looking for authentic alternatives to overtouristed destinations. In 2019, Greece welcomed a record 34 million visitors, but like everywhere else, tourism took a massive hit during the pandemic (numbers fell to around 7 million in 2020). Predictions are buoyant for 2022, with developers racing to meet increased demand. Half a dozen new hotels are opening this summer on Santorini alone, including Greece’s first Nobu hotel, a 59-room Hyatt, and a Radisson Blu resort. The W chain is soon to have its Greek debut as part of a collection of high-end resorts in the Peloponnese, and will be joined by a Mandarin Oriental in 2023.
But look beyond these international brands and you’ll find that the lesser-known islands are peppered with small, soulful properties that offer a far more personal experience. Last summer, I visited three such hotels on three very different islands: the Aristide on Syros; the Rooster, a low-impact retreat on Antiparos; and 1900 Hotel, a four-room hideaway on far-flung Symi. While each property has its own distinctive personality and backstory, all three are embedded in the landscape and the community, and all are run by first-time hoteliers driven more by passion than by profit. Because the owners are involved in every aspect of operations and have spent years getting to know the destination, each hotel made me feel like I was a special guest, rather than just another room number.
It takes chutzpah to open a hotel during a pandemic. When the hotel is in a historic neighborhood on a small Greek island and you have zero experience in hospitality, some might call it madness. But that’s exactly what sisters Oana and Jasmin Aristide did. “We fell in love with Syros and wanted to buy a modest holiday home,” Oana said. “But the moment we saw this house, our plans changed. I suppose we were the only people naïve enough to take it on.” It took four years, and a deep dive into the vagaries of Greek bureaucracy, to transform the abandoned Neoclassical palazzo into the nine-suite Hotel Aristide.
Soft-spoken but unstoppable, Oana quit a career as an economist in London to manage the project; to help fund it, her sister, Jasmin, spent long months working as a substitute doctor in the Swedish Arctic. With Greek ancestry, Romanian-Yemeni parentage, and an upbringing that took them from Transylvania to Sweden as refugees, the Aristide sisters are as cosmopolitan as their adopted island.
Almost half the population of Syros is Catholic, a legacy of the three-century Venetian occupation that began in the Middle Ages. During the Greek War of Independence (1821–32), the shrewd locals avoided taking sides, securing the island’s status as the Switzerland of the Aegean — neutral and rich. As more rebellious islands were crushed by the Ottomans, wealthy merchants, bankers, and businessmen fled to Syros. “They left behind a city almost too ambitious for this little island: a place of marble pavements, palatial buildings, and Neoclassical squares,” Oana told me over a glass of the local Assyrtiko wine and a selection of Cycladic cheeses in the hotel’s hidden garden.
The sisters make a point of promoting local and sustainable products at the Aristide. There’s also a refreshing use of color throughout the hotel: soaring ceilings are painted white, mustard, teal, or pink. Each suite is named after a different type of Greek marble, used to dazzling effect in the bathrooms. Toiletries made with aloe and prickly pear come in ceramic jars (the sisters decided against single-use plastics in the hotel). The “contemporary Cycladic” dinner menu changes daily, depending on what’s in season in the hotel’s organic garden and whatever their favorite fisherman brings in.
Over the course of a sybaritic long weekend, Oana and I shared deconstructed dishes at Avant Garden and botanical cocktails at Theosis, a tiny bar in the medieval fortress of Ano Syros. My favorite lunch was at Iliovasilema, where the whipped tarama is blended with squid ink and the grouper is served on smoky eggplant.
You might hear live rebetiko (the gravelly Greek blues whose godfather, Markos Vamvakaris, hailed from Syros) at the wonderful bistro Cantina Analogue. Instead of exploring ancient ruins, you can take a night tour of a deserted textile factory with Hermoupolis Heritage, a nonprofit dedicated to preserving the island’s illustrious past. The wonderful thing about Syros — and indeed the Aristide — is that old and new collide in surprising and delightful ways.
At first glance, Gialos, the handsome port of Symi, could be a miniature version of Hermoupolis. Tiers of Neoclassical houses in every shade of ocher and terra-cotta ascend, amphitheater-like, from the harbor. Many of them were built in the 19th century, when this speck in the Aegean became a wealthy trading post thanks to the island’s sponge divers. They trawled the seabed in mechanical diving suits, known locally as skafandra — a German invention brought to the island by an enterprising seaman named Fotis Mastoridis. None of the local men were brave enough to try the suit, until Mastoridis’s pregnant wife, Evgenia, took the plunge. “It was a turning point for the island’s fortunes,” said Dimitris Zographos, an architect on a mission to preserve Symi’s heritage.
Last year, Zographos realized a long-held dream: he leased the quayside mansion that Mastoridis built for his family and within six months had transformed the derelict property into a glamorous yet informal guesthouse — one with no reception, no restaurant, and no room service. Guests can help themselves to coffee and cookies in the parlor or drinks from an honor bar on the landing, where musicians once serenaded visitors in evening dress. The upstairs terrace is decorated with colorful rugs and deck chairs — front-row seats for some of the best people-watching in the Mediterranean. Painted dusky blue and green, the four suites each have unique details like original cement tiles or elaborate ceiling paintings, offset by Thonet chairs or antique cabinets.
Like most Greeks, Zographos is an exceptionally thoughtful host. Despite my painfully early morning arrival, he welcomed me off the ferry and led me along the waterfront, pausing every few yards to greet fishermen, café owners, and chic Italian and French homeowners. “Symi attracts people who appreciate beauty, landscape, and space,” he said.
The Greek ministry of culture declared the whole of Gialos a historic monument in 1971, and the island is protected by three different preservation orders. “Eighty-nine percent of the land is classified as forest, and we’re not allowed to build on it,” he noted. “So what you see today is hopefully not very different from what you might see a hundred years from now.”
Zographos doesn’t have a car, or even a driver’s license. You don’t need wheels on Symi: the main road peters out at the Monastery of Panormitis, a popular day trip from the nearby island of Rhodes. Panormitis is impressive, but there are many more remote monasteries, hidden deep in forests of cedar and cypress.
When it’s too hot for hiking, the best way to explore is by boat — whether it’s a RIB, a yacht, a gulet chartered on the nearby Turquoise Coast of Turkey, or one of the water taxis that service the dazzling beaches on the eastern coast. (Nanou, with a tribe of cheeky goats and a beach shack that serves flash-fried shrimp, is extra special.)
Although thousands of yachts anchor around Symi every summer, there are still coves where you can skinny-dip in solitude. Zographos can arrange for a skipper to drop you off; he might even take you for a spin in his speedboat, with a stop for lunch at his favorite taverna on Toli Beach, Dafnes. “That side of the island is totally undeveloped,” he said. “It’s like Greece in the 1960s.”
1900 Hotel: Symi is one hour by ferry from Rhodes, which is served by domestic flights.
“It’s been quite a ride,” said Athanasia Comninos, CEO and founder of the Rooster. A decade ago, Comninos pitched up on the tiny island of Antiparos with her baby and her best friend, tired of Mykonos and tired of life. The only daughter of a Greek shipping magnate, she had lost her sense of direction after a painful divorce. “Antiparos instantly felt like home,” she told me. “It’s an island where you can take it easy. You can party or you can disappear.”
The Rooster is just the place to slip off the radar. Sixteen villas built of local stone blend into the sunburned hills overlooking the empty sweep of Livadia Bay. Interiors are spacious but spare, a quiet symphony of natural materials. Life at the Rooster is conducted outdoors. Every house has a private pool surrounded by flowering shrubs in which tiny yellow-breasted birds nest. Sun salutations and sound-healing sessions take place in an open-air pavilion. A kind, khaki-clad waiter in Vans sneakers will bring a picnic wrapped in starched linens to the beach, which is blissfully lacking in sunbeds. At dusk, a good-looking but low-key crowd in velvet slippers and patterned caftans drifts toward the hilltop bar, which faces the sunset and is open to the elements. At night, you can see millions of stars.
“The whole idea was not to disturb but to preserve the landscape,” said Comninos, who owns a summer house just across the valley. Although she always dreamed of being a hotelier, it was only after a life-changing trip to the resort Chiva-Som, in Thailand, that the idea of opening her own wellness retreat on Antiparos took root. It took eight years to go from idea to reality. Throughout, she collaborated closely with Vois architects, a practice run by two women who own houses on Antiparos and share Comninos’s deep affection for the island.
Separated from the bigger, brasher island of Páros by a narrow strait, Antiparos has always had a slightly rebellious feel. The hippies who first “discovered” it in the 1980s still stay at the campsite and prop up the bars in the pint-size harbor town. Scandinavian families return year after year, lured by the calm, shallow bays — you’ll find them in the hammocks at Time Marine, a bar on Psaralyki Beach, lunching at the taverna Peramataki (30-228-406-1211), which overlooks Soros Beach, or trying on sandals at Zali, one of many boutiques in Antiparos town.
Whichever beach tribe you belong to, there’s a simplicity to life on this low-slung island that gets you straight into the vacation mindset. You could sweet-talk the chef, Andreas Nikolakopoulos, into showing you around the Rooster’s organic farm (when he isn’t perfecting his zucchini-blossom risotto, he writes short stories and rides a vintage motorcycle). Book a Reiki session with Comninos’s spiritual teacher at the House of Healing, or ask her buddy Giorgos Marianos (a.k.a. the Pirate) to sail you across to the temple of Apollo on the deserted island of Despotiko. Or you could just lie back with a glass of something chilled and stare up at the blue sky. On Antiparos, less is more.
The Rooster Antiparos: Antiparos is a 10-minute ferry ride from Páros, which is served by regular flights (40 minutes) and ferries (three to five hours) from Athens.
A version of this story first appeared in the June 2022 issue of Travel + Leisure under the headline Greek Trilogy.