On the serene Aegean island of Ios, the late-season sun bathes mineral-rich sand in golden light, and the breeze is soft—no longer swept away by the famous Meltemi winds of summer. In this calm, luxurious pocket of Greece, discerning travelers trade the crowded peak season for a slower, more meaningful escape. At Calilo, an art-drenched resort perched on ochre cliffs, a sophisticated (and privacy-loving) clientele settles into mosaic pool suites, wanders through olive groves, and dines beside sculpture-lined reflecting pools—all in blissful seclusion.
It may surprise some to know this isn’t the high summer season. It’s September. And for luxury travelers in the know, this “shoulder season” is quickly becoming Greece’s most desirable time of year.
“September is a special time to visit Ios,” says Angelos Michalopoulos, the resort’s co-owner and a former Wall Street broker turned self-taught artist, writer, and hotel designer.
“The summer light can be harsh. But in September, it’s softer, more diffused. The seas are calm, and the crowds are gone. For creating art—and enjoying the island—it’s the ideal time”
Indeed, a yacht trip around Ios in autumn feels like a private tour: cerulean coves are virtually empty, beaches are silent save for the occasional bleat of a goat, and the charming tavernas in Chora no longer have waitlists. What was once a bustling summer destination transforms into an exclusive retreat.
The same is true across the Cyclades. On nearby Santorini—a 40-minute ferry ride away—the chaotic crowds of August ease off. Though the island welcomed 3.4 million visitors in 2023, a growing number are now choosing to come in September and October, lured by the extended warm weather, tranquil atmosphere, and increasing availability of luxury accommodations.
“We only opened in July, but September has been as busy as August,” says Evangelia Pantazi, senior sales manager at Sandblu, a new retreat in Santorini’s up-and-coming Kamari region. With its half-moon infinity pool, sea views, and ancient ruins, the resort is now attracting couples, digital nomads, and retirees.
“It’s a different crowd—more peaceful, more interested in soaking in the island’s true beauty”
Charlotte Wells, Global Product Manager at Abercrombie and Kent, echoes this sentiment. “September has become the new sweet spot for a Greek getaway,” she says.
“The crowds have thinned, the weather is still glorious, and travelers are beginning to explore lesser-known gems”
Among those hidden treasures is Folegandros, where the recently opened Gundari resort offers sleek luxury in a rugged, untouched setting. Or consider Tinos, now home to Odera, the first true luxury property on the island, part of Marriott’s Autograph Collection. With 77 sugar-cube-style suites overlooking Vourni Beach, it’s a quiet paradise. Meanwhile, on Syros Island, the neoclassical charm of the Agini Hotel—with restored frescoes and designer lighting—makes it one of Greece’s most unique boutique stays.
On the Peloponnesian coast, Mandarin Oriental, Costa Navarino, opened in August 2023 and is now extending its season beyond summer. General Manager Raul Levis explains:
“We’re seeing a growing trend towards year-round travel, especially with interest in wellness, golf, and experiences like olive harvesting in late October. Autumn in Greece isn’t just beautiful—it’s culturally ricH”
Back on Ios, Michalopoulos and his wife, Vassiliki Petridou, founder of the LuxurIOS group, are already looking ahead. They plan to open four new suites at Calilo for next season, with seven more coming by 2026. Their vision is clear: position Ios not only as a summer hotspot but a destination for reflection, connection, and immersive luxury in every season.
“As we look to the future,” says Petridou, “we see Ios and Calilo becoming a magnet for those who value tranquility, cultural immersion, and off-the-beaten-path exploration. The 2025 season and beyond holds the promise of even more meaningful journeys”
If you’re seeking Greece at its most authentic, elegant, and serene—look past the crowded heat of July and August. September and October are the months when the true soul of the Aegean quietly shines.
