Tailor Made Holidays - Island Hopping in the Cyclades

Discover the lesser-seen stars of Greece’s most celebrated island group.

We love a holiday that starts at a bustling port, and there’s something rather special about heading to an island that is only accessible by sea.

The Cyclades offer just this, and the lack of direct flights mean the islands retain their sleepy, authentic feel with little of the price-elevating that occurs on flashier neighbours Santorini or Mykonos. It’s possible to hop from one island to another giving you a peaceful passage around the lesser-seen Cyclades, where charming hotels await, rural life remains unchanged for centuries and dazzling beaches are devoid of tourists.

Slipping into Cycladic life on an island-hopping adventure
Celebrating Sifnos’s culinary heritage as you trot between tavernas
Hopping between hot springs and limpid blue bays on geothermal Milos
Watching the sunset from the clifftop church Panagia on far-flung Folegandros
Sampling local liqueurs then snoozing in the sun on Naxos’s beautiful beaches

It’s easy to follow the well-trodden route through the Cyclades from Mykonos to Santorini. But with simplicity comes crowds, cruise ships and some hefty price tags. This 15-day island-hopping trip takes in some of the smaller, quieter islands of the Cyclades, where rural life has changed little in centuries, and dazzling beaches are devoid of tourists.

Discover the lesser-seen stars of Greece’s most celebrated island group.

We love a holiday that starts at a bustling port, and there’s something rather special about heading to an island that is only accessible by sea.

Slipping into Cycladic life on an island-hopping adventure
Celebrating Sifnos’s culinary heritage as you trot between tavernas
Hopping between hot springs and limpid blue bays on geothermal Milos
Watching the sunset from the clifftop church Panagia on far-flung Folegandros
Sampling local liqueurs then snoozing in the sun on Naxos’s beautiful beaches

What

A 15-day island-hopping trip through four of the quieter islands in the Cyclades, staying at boutique hotels full of charm and character.

Best For

Anyone looking to swap the crowds and the cruise ships of Mykonos and Santorini for more traditional Greek charms. It would also make a lovely island-hopping honeymoon - talk to us about designing this special trip for you.

When To Go

Travel is possible from April through to October. July and August are peak months, when temperatures soar and even the quieter islands get crowded. If you ask us, the best months to visit are May, June and September.

Day 1-4

Sifnos

Travel by ferry from Piraeus in Athens to Sifnos, whose three whitewashed villages sit like pearls along the crest of the island. Olive groves, almond trees, oleander and fresh herbs flank the slopes of the central mountains, and every evening the sun sinks into the Aegean to reveal a panoply of stars in the clear night skies above.

As serene as Sifnos is, it’s not actually the scenery that steals the show here, but rather the food. Nicholas Tselementes was born here. He wrote the first Greek cookbook in 1910 and Sifnos has been a mecca for Greek manna ever since. From traditional tavernas to celebrity-chef restaurants, eating out on Sifnos is always a delight.

Stay

Verina Astra

Soak up the sensational seascapes from your private terrace at Verina Astra, a secluded clifftop residence with just seven suites. Although less than a mile from Artemonas, the prettiest of Sifnos’ whitewashed villages, all you’ll hear here are the jangling of goat bells, the thrum of cicadas and the whistling of the wind.

Day 5-8

Milos

Onwards to Milos, the volcanic island where the Venus de Milo was discovered by a farmer in 1820, before it was spirited off to the Louvre. There’s more to appreciate here, though, than just a place in art history. The island arches around a central caldera and is ringed by one of the most diverse and dramatic coastlines of all the Greek islands.

Between the colourful and surreal rock formations – shaped by the minerals that have long been a source of wealth here – are dozens of beaches (more than on any other island in the Cyclades), natural hot springs, bays of sapphire blue water, a protected nature reserve and a series of picturesque villages.

Scenic Klima village, Milos, Greek Island

Stay

Phos Milos

Just steps from the beach that sits in front of the fishing village of Pollonia, Phos Milos is a vision in white, a modern and minimalist take on Greek architecture which imbues its collection of suites and rooms. The suites in particular are spacious and flooded with light, benefiting from COCO-MAT sleep products and cooling plunge pools.

Day 9-11

Folegandros

Now’s the time to take slow-lane living down a further notch. Beautifully unspoilt Folegandros is tiny – just eight miles long, with a couple of hundred inhabitants who share the island with rambling, bell-chiming goats. From the clifftop capital Hora, easily one of the most appealing villages in the Cyclades, zigzagging steps lead up to the island’s only real landmark, the looming Panagia church – go at sunset or sunrise for some incredible photo backdrops.

Several beaches are serviced by water taxis, while others can be reached by a scramble down rocky footpaths. Don’t expect sand and sunbeds though; think pretty pebbled coves and limpid blue water that cries out to be swum in.

Anemi, Folegandros, Cyclades, Greek Island

Stay

Anemi

Anemi’s 44 white-sugar-cube suites are a study in minimalist architecture, the bright whiteness of the bedrooms offset only by the largescale modern artworks used as headboards. All have verandas, some have private pools, and all channel the eye towards the heart-stopping views over Karavostasis Bay. And after the island’s cliffs and beaches have inevitably drawn you out, Anemi’s amazing restaurant will just as surely draw you back.

Day 12-15

Naxos

End your loop through the Cyclades on Naxos, from which you can catch a flight home via Athens. Although the largest of the Cyclades, it’s still relatively easy to get away from it all on Naxos. The west coast, in particular, is fringed with mile upon mile of powdery beaches, some with shallow waters great for swimming, others wilder and more open, fit for windsurfing, kitesurfing and galloping on horseback.

Hidden in the hills you’ll find dozens of drowsy villages, two giant marble statues from the 6^th and 7^th centuries BC, as well as liqueur distilleries, olive oil presses and some venerable vineyards.

Stay

18 Grapes

Enjoy a warm welcome at chic, boutique hotel 18 Grapes, a 20-minute drive from Naxos town. With just 18 rooms, this family-run hotel has a laid-back ambience with a pool, spa and rooftop garden adding to its appeal. The hotel also has its own vineyard and tasting room which you can tour with one of the team, learning about Naxos’ thousand-year-old wine history.