On the brilliant blue Aegean, the mineral-rich sand shimmers, the sun beams, and a wealthy, generally American clientele hides out in huge monochrome marble and mosaic pool suites that cling to ochre bluffs on the isle of Ios. Some surface to breakfast at sunken tables set inside reflective pools aside a sculpture dotted swimming pool. Others might wander the olive gardens or peer inside the kaleidoscopic Orthodox chapel. In the evening, a few more come to drink cocktails under a neon sign reading “Create a Life You Can Fall in Love With,” words that the name of this resort, “Calilo,” were pulled from.
But this isn’t the height of summer, the peak time to visit Greece and this art-crammed boutique hotel. Instead, these privacy-obsessed masters of the universe have arrived for the typically sleepy shoulder season. So what do they know that you don’t?
“September is a special time to visit Ios,” says the Calilo’s owner, ex-Wall Street broker and self-taught artist, writer, and hotel designer Angelos Michalopoulos. “In the summer, the light can be quite harsh. In September, the light is softer and more diffused. The famous Meltemi winds have settled so it’s warm, but we have calm seas. For me, the conditions are ideal for creating art. The harmony of the island really shines at this time of year—and all without the summer crowds.”
Indeed, a yacht trip around the island reveals only a handful of other boats, turning cerulean lagoons into private swimming pools. And while there’s a sociable air at Chora’s tavernas, there’s no queuing for a table. In the island’s little dusty villages and on the empty beaches, you’ll spy more goats than vacationers during the one-hour drive from the port to Calilo’s remote home on Papas Beach.
Across Greece, big spenders are ditching party spots at the height of summer in favor of quieter retreats.
Even the ultra-competitive summer atmosphere on the island of Santorini—a 40-minute ferry from Ios—mellows at this time of year. With just roughly 20,000 year-rounders, the island’s population swells in the summer. There were 3.4 million visitors in 2023, leading locals to call for a cap.
“We only opened in July, but September has been as busy as August,” says Evangelia Pantazi, senior sales manager at Sandblu, a new luxury retreat in up-and-coming Kamari, with 61 rooms and suites, a glorious sea view half-moon infinity pool and its own ancient ruins. “But the crowd is different. In summer, we have lots of families, but in September the kids are back in school, so we have more couples, retirees, and younger people who can work from anywhere.”
Abercrombie and Kent’s global product manager, Charlotte Wells, agrees that the demographics are changing.
“We’re seeing a definite shift in traveller preferences, with September emerging as the new sweet spot for a Greek getaway,” she says. “The crowds have thinned, and the weather is still glorious.”
But Wells emphasizes that it’s not just about knowing when to go but where to go: “We highly recommend exploring hidden gems like Folegandros, also in the Cyclades, where the new Gundari resort just opened. These lesser-known islands offer stunning landscapes, tranquil beaches, and a slower pace of life that’s perfect for a relaxing escape.”
Want the best rooms at better rates? Fall is your time to shine.
CHRISTOS DRAZOS
Other new autumnal options might include the cypress and honeysuckle swept isle of Tinos, where Autograph Collection recently opened the island’s first luxury hotel of note, Odera, with 77 sugar-cube rooms and suites staring out over Vourni beach. Or consider Syros Island, where the new Agini Hotel beckons. Located in the chalky pink and yellow town of Ermoupolis, a 15-minute walk from the beach, it has 11 rooms set inside a 19th-century neoclassical pile. Interiors blend restored Renaissance-style frescoes and gilt trim with contemporary furniture, lighting, and ceramics from Poltrona Frau, Tooy, Astro, and Artemide to beautiful effect.
“We are seeing a growing trend towards extending the season, especially due to increased interest in our golf offerings,” adds Raul Levis, general manager of Mandarin Oriental, Costa Navarino, which opened on a molten-gold beach in the ruin-riddled Peloponnese in August 2023. “We are now actively exploring the possibility of more winter offerings that could allow us to cater to guests year-round, expanding our appeal across all seasons.”
Calilo is one resort that’s pouring its resources into the shoulder season.
Courtesy of Calilo
Beyond their four signature golf courses, year-round activities might include philosophy walks with classical scholars through the idyllic Messinian countryside, deep-reaching wellness retreats, or participating in the late October olive harvesting. The type of activities which will particularly appeal to Europeans, Americans, and citizens of sweltering South East Asian and the Middle Eastern countries, who don’t necessarily travel just for the sun.
Back on Ios, Michalopoulos—along with his wife, Vassiliki Petridou, founder of LuxurIOS group, and four of their five children—are planning to four new pool suites to Calilo in time for the season (and off-season). In 2026, they’ll add another seven suites.
“As we look to the future, we see Ios and Calilo becoming a magnet for those who value tranquility, cultural immersion, and off-the-beaten-path exploration,” say Petridou. “The 2025 season and beyond holds the promise of welcoming even more discerning travelers who yearn for a deeper connection with themselves, the environment, and the authentic spirit of the Cyclades.”
Credit: robbreport.com
