When the peak-summer frenzy subsides, Greece’s islands enter their most enchanting season. September brings gentle sunshine, warm seas perfect for swimming, and pleasantly cooler evenings, making it ideal for both relaxation and adventure. With the crowds gone, you’ll experience island life in a more rustic light – strolling uncrowded beaches, savoring seasonal flavors, and joining in local festivals that celebrate harvests, music, and tradition.

From Cycladic gems to Crete’s cultural riches, these five islands are the ultimate late-summer escape, blending natural beauty with the warmth of community.

Mykonos

Known as the party island, Mykonos takes on a gentler rhythm in September. The weather is still sun-soaked and its famous beaches – Panormos, Elia, Super Paradise – are blissfully uncrowded. Nightlife continues but with less intensity, striking a sweet balance between energy and tranquility. This is the moment when Mykonos feels more like a village again, and visitors can slip into its slower pace.

September also brings two important cultural celebrations. On the second Sunday of the month, the Harvest Festival takes place at the open-air Agricultural Museum at Mylos tou Boni, part of the superb Folklore Museum. Guests can sample freshly baked bread and other treats, sip local wine, and enjoy traditional music and dancing beneath the iconic stonework windmills, overlooking Hora – a joyful nod to the island’s agrarian roots.

On the same Sunday (September 14), locals gather in the inland village of Marathi for the Feast of the Holy Cross, also known as the Exaltation of the Holy Cross, one of the Great Feasts of the Orthodox Church. This important festival, celebrated on the anniversary of the day on which St. Helena found the True Cross, is accompanied by food, music, and traditional dancing.

Together, these festivals offer travelers a chance to share in Mykonos’ local traditions, beyond the much-vaunted clubs and cocktails.

Naxos

The largest of the Cycladic islands, Naxos combines endless sandy beaches, stunning archaeological sites, and hearty local food. Now the summer heat has mellowed, September is ideal for hiking through its mountain villages such as Apeiranthos and Halki, which are often missed off summer itineraries, while local flavors are at their peak – figs, potatoes, cheeses, and the first new wine of the season.

Culture thrives on Naxos well into September. The long-running Naxos Festival at Bazeos Tower, Kampos of Agiasos (12km south of Hora) brings concerts, art exhibitions, and theatrical performances into the atmospheric setting of a 17th-century monastery-turned-cultural space. The Dionysia Festival in Hora, usually held in early September, honors the ancient Greek god of wine with a lively program of music, theater, and art, culminating in a communal wine feast. Food lovers may also encounter the Naxos Wine Festival and/or Gastronomy Week, with tastings, workshops, and special menus that showcase the island’s abundant produce.

Other traditions keep the spirit of community alive: concerts at the Domus Cultural Festival in the heart of medieval Kastro, which runs from April to October, and religious feasts such as the Panagia (Virgin Mary) Theoskepasti on September 8 in the villages of Komiaki and Potamia.

Dates can shift, so it’s wise to ask locally – part of the fun is stumbling across a celebration you didn’t expect.

Crete

As Greece’s largest island, Crete offers a world of experiences: pink-sand beaches like Elafonisi, the dramatic Samaria Gorge, and Minoan treasures such as Knossos. September’s milder weather makes road trips, hiking, and sightseeing far more comfortable than in high summer, while village squares come alive with cultural and religious celebrations.

Several major festivals extend into September. In Hania, the long-running Summer Festival features concerts, theater, and art exhibitions across the city, while the Chaniartoon Festival (September 20–28), held in the Municipal Garden’s open-air cinema, showcases animated films and comic art from international creators. In Iraklion, music lovers should look out for the Ametric Festival (September 12–13), which transforms the atmospheric Venetian San Salvatore Bastion into a space for experimental soundscapes and electronic music.

Beyond the cities, tradition takes center stage. Around September 13–14, the villages of Aptera and Maza host the Feast of the Holy Cross (“Timio Stavros”) with communal gatherings, folk dancing, and plenty of local food, wine, and the obligatory “tsikoudia” – Cretan raki. September also marks the grape harvest, and the villages of Archanes and Sitia celebrate with lively wine festivals.

Many events are local and spontaneous – part of Crete’s enduring charm – so it pays to keep your eyes and ears open as you explore.

Syros

Elegant and cultural, Syros offers a different kind of Cycladic escape. Its capital, Ermoupoli, is a neoclassical showpiece – grand mansions, marble squares, and a stately waterfront – its layered history marked by a rare blend of Orthodox and Catholic traditions. The island is currently undergoing a cultural renaissance of sorts, hosting more than 50 events under the banner “Syros – Culture 2025” from May through November. With the peak-season crowds gone, now is a fabulous time to visit.

Two standout festivals anchor the month. From September 11-14, the Syros Jazz Festival returns for its 13th edition. This year’s theme explores collaborations across generations, with concerts by acclaimed Greek and international musicians, plus film screenings, comic art, workshops, and even design exhibitions by students of the University of the Aegean.

Later in the month, September 22–28, the island hosts ANIMASYROS, Greece’s premier animation festival and one of Europe’s most important. The 2025 theme, “Animated Cosmos,” will be explored through screenings, exhibitions, parties, and educational programs.

Between concerts and screenings, you can slip away to one of Syros’ quieter beaches – like Kini or Galissas – or simply enjoy the relaxed café culture. In September, Syros shines as Greece’s true “island of culture.”

Tinos

Known for its spiritual heart, the Church of Panagia of Tinos, and its artistic heritage in marble carving, Cycladic Tinos blends devotion, creativity, and natural beauty. Like its neighbor Syros, the island is recognized for its strong Orthodox and Catholic traditions; every August 15, thousands of pilgrims arrive for one of the country’s largest religious celebrations, the Feast of Assumption. By September, however, the atmosphere softens, making it an ideal time to wander through whitewashed villages, hike scenic trails, or sample the island’s emerging gastronomy scene – from boutique wines to artisanal cheeses.

Culture and community remain at the forefront this month. The summer-long Tinos Festival, which runs through September, brings concerts, theater, and exhibitions to towns and villages across the island. Keep your eyes peeled for local events. On September 14, the village of Ktikados celebrates the Festival of the Holy Cross, where Catholic and Orthodox communities alike join in liturgy, music, and dancing in honor of their neighboring historic churches – the Catholic church is one of the oldest on the island.

Just a day later, from September 15–17, the island’s Wine Festival offers tastings of windswept Tinos’ distinctive vintages, guided tours, and food pairings, all accompanied by live music. Together, these events make September on Tinos a chance to experience both its deep-rooted traditions and its creative, contemporary spirit.