The ultimate Cyclades island hop

About The ultimate Cyclades island hop

By the ULTIMATE Athens Editorial Team

Eleven islands, a dozen ferries and one unforgettable summer. This is our ultimate island hop through the Cyclades: from the old port of Piraeus to elegant Syros and holy Tinos, glamorous Mykonos, easy-going Paros and green Naxos, wild Amorgos, lively Ios, volcanic Santorini, unspoilt Folegandros, delicious Sifnos and, last of all, the white rocks and sea caves of Milos, before a short flight home to Athens.

The dream

There is a moment, somewhere between two islands, when the ferry’s engines settle into a steady hum, the wind tugs at your hair and the next island rises out of the haze: a smudge of brown hills, then a sprinkle of white houses, then a harbour full of fishing boats. Do it eleven times in a row and you will understand why island hopping in the Cyclades is one of the great journeys of the world.

This is our ultimate route: from Piraeus by ferry through all eleven islands in our guide, from elegant Syros to wild Milos, then a short flight home to Athens: three nights on every island, 34 days in all, about five weeks of the best summer of your life.

Somewhere between two islands, the engines settle into a steady hum, and the next island rises out of the haze.

Piraeus to Syros: the capital of the Cyclades

Catch the early ferry from Piraeus, coffee in hand, as the ferry slips past the cranes and out into the Saronic Gulf. Your first island is Syros, the surprising capital of the Cyclades. In the 19th century, Ermoupoli was the busiest port in Greece, and its merchants built a city of marble mansions, a grand town hall by Ernst Ziller on Miaoulis Square and the Apollon Theatre, a miniature opera house modelled on Italian theatres. Above it, the medieval hilltop town of Ano Syros has been Catholic for centuries. Buy a box of loukoumi, the island’s famous sweet, before you leave.

Tinos: faith, marble and dovecotes

A short hop away, Tinos is one of the most authentic islands in the Aegean. Pilgrims from all over Greece come to the great Church of Panagia Evangelistria, some crawling on their knees up the long road from the harbour, and the island’s countryside is dotted with hundreds of ornate dovecotes and villages of marble. In Pyrgos, home of generations of marble sculptors, the doorways and fountains are works of art, and the food, from artichokes to local cheeses, is among the best in the Cyclades.

Mykonos: glamour and an island of the gods

Next comes Mykonos, the most glamorous island in Greece, with its whitewashed lanes, the windmills of Kato Mili and the captains’ houses of Little Venice rising straight from the sea. Watch the sunset with a cocktail, then dance until late. Make time for a boat to Delos, a short ride away: in myth the birthplace of Apollo and Artemis, it was one of the holiest places in the ancient world, and today the whole island is an open-air archaeological site.

Paros: the perfect all-rounder

Paros is the island we recommend most to first-timers, and it rarely disappoints. In Parikia, the Panagia Ekatontapyliani, the Church of a Hundred Doors, is one of the oldest churches in Greece. In the north, Naoussa’s little harbour is packed with fishing boats and waterfront tavernas, and inland the hill village of Lefkes sits at the start of the Byzantine path, a paved medieval track down to the coast. Take the small boat across to Antiparos for a lazy afternoon.

Naxos: big, green and full of myths

Naxos is the largest and greenest of the Cyclades, an island of mountains, valleys and long sandy beaches. Its symbol is the Portara, the great marble doorway of an unfinished temple of Apollo begun in the 6th century BC, which stands alone on an islet by the harbour; according to legend, it was here that Theseus abandoned Ariadne. Above the port, the Venetian Kastro is a maze of old mansions, and in the mountains the marble village of Apiranthos feels a world away from the beach.

Amorgos: the deep blue

Amorgos is wild, long and mountainous, and its water is the deepest blue in the Aegean, as the film The Big Blue showed the world in 1988. Its great sight is the Monastery of Panagia Hozoviotissa, a whitewashed wall built into a sheer cliff hundreds of metres above the sea, founded in the 11th century. Walk the old mule paths between the villages, swim in empty coves and slow down: this is the island where people come to switch off.

Ios: party island with a softer side

Ios made its name as the party island of the Cyclades, and in high summer the bars of its Chora still fill with young travellers. But outside the late nights, it is beautiful: a hilltop Chora of white houses and blue-domed churches, the long golden beach of Mylopotas, and a northern hillside where, according to local tradition, Homer is buried.

Santorini: the volcano

Then comes the most dramatic arrival of all. As the ferry sails into Santorini, the cliffs of the caldera rise hundreds of metres above you, with the white villages of Fira and Oia perched along the rim like snow. About 3,600 years ago, a colossal eruption blew the heart out of the island, burying the Bronze Age town of Akrotiri in ash and leaving behind the flooded crater you are sailing across. Walk the clifftop path from Fira to Oia, taste the island’s Assyrtiko wines and stay for a sunset.

Folegandros: small and unspoilt

After Santorini, Folegandros feels like a deep breath. Its Chora sits on the very edge of a cliff, with squares shaded by trees, tiny tavernas and the old Kastro whose houses form its walls. Climb the zigzag path at sunset to the church of the Panagia above the town, and you will see why so many travellers call this their favourite island.

Sifnos: the food lover’s island

Sifnos is where Greeks go to eat. The island gave Greece its most famous cookbook author, Nikolaos Tselementes, and its potters still work the local clay into the dishes that slow-cooked revithada, a Sunday chickpea stew, is baked in overnight. Walk to the monastery of Chrysopigi on its rock by the sea, wander the medieval village of Kastro, and eat as well as you will anywhere in Greece.

Milos: the grand finale

Finish on Milos, the island with the most extraordinary coastline in the Aegean. The white volcanic rocks of Sarakiniko look like the surface of the moon, the sea caves of Kleftiko were once a pirates’ hideout, and the fishing villages of Klima and Mandrakia have brightly painted boat garages built into the water. It was here, in 1820, that a farmer found the statue now known as the Venus de Milo, today one of the treasures of the Louvre.

Flying home

On your last morning, take a final swim, then head to the little airport for the short flight back to Athens, less than an hour in the air. As the islands slip away beneath you, you will already be planning the next trip.

When to go and how to book

The best months are May, June, September and early October, when the sea is warm, the light is soft and the ferries are less crowded. In July and August, the strong meltemi wind can make crossings rough and occasionally delays or cancels smaller boats, and everything is busier, so book ferries and rooms well ahead. Not every route sails every day, so check timetables before you fix your plan, and keep a spare day in hand for the weather.

Our advice: travel light, because you will be carrying your bags on and off a dozen boats. Book your ferries as soon as timetables are published, ideally on one app so all your tickets are in one place, and arrive at the port at least 30 minutes before departure. Choose conventional ferries when the sea is rough: they are slower but much steadier than the fast catamarans. And do not try to see everything on every island. The magic of the Cyclades is in the long lunches, the late swims and the evenings watching the boats come in.

The route at a glance

Ferry routes and timetables change with the season and not every connection runs daily; check the latest sailings before you book, and keep a spare day for the weather.

Opening hours, prices and seasonal openings change, so please check with The ultimate Cyclades island hop before you go.