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Greek Island Hopping Cyclades

This two week journey combines ancient Athens with two of the most iconic islands - cosmopolitan and sophisticated Mykonos and dramatically picturesque Santorini – and for some real switch off time there are lazy days on the fine white sands of Naxos.

Greek Island Hopping in the Cyclades

The lowdown

  • Getting there

    Ferries and hydrofoils to the Cylcades depart from Athens and it is also possible to fly directly from the UK to Mykonos and Santorini. Ferry schedules vary depending on the season but we can pre-arrange tickets.

  • When to go

    Pleasant temperatures and fewer crowds make June and September the perfect months to tour the islands. Santorini is very popular so hotels need to be booked ahead for summer.

  • Combine with

    Smaller Cyclades islands such as Tinos, Sifnos and Folegandros – almost as spectacular as Santorini but without the crowds.


The Cycladic islands are characterised by white washed houses, turquoise blue seas, olive groves and sun drenched landscapes..

Each island is stamped with its own unique character and the best way to discover their unhurried charm is by ferry. Nothing beats the sense of freedom that pervades as you glance up from your holiday novel  – Cartes Postales from Greece? –  to take in the shimmering Aegean Sea as your next destination emerges on the horizon.

  • Visit and explore the Acropolis, the quintessential landmark of Western civilization.
  • Experience the amazing cosmopolitan (night) life of Mykonos.
  • Take a boat trip to explore sacred Delos with a private guide.
  • Hike in the mountains of Naxos in off beaten routes and visit its remote whitewashed villages.
  • Paddle towards the famous Santorini Red Beach and admire the soaring red lava cliffs.
  • Experience a boutique winery visit and taste a variety of Santorini Grand Crus.


Athens is a city with more than 6,000 years of history and delivers a colourful and vibrant start to your travels.  Our privately guided tours will unravel the history of the most iconic sites of Ancient Athens –  Acropolis, Temple of Olympian Zeus, Temple of Poseidon – but you will have plenty of time to explore Plaka and Monastiraki neighbourhoods, where traditional Greek tavernas spill onto the labyrinthine alleys and pedestrianised streets.


The fastest ferries take 4-5 hours to reach Mykonos – you can also fly if you like but you’ll be missing out – sometimes referred to as the St Tropez of the Aegean. The island boasts beaches – with powdery white sand – but it is the chic bars, elegant restaurants and lively nightlife that attracts so many visitors each year.  It’s ok to give into some swanky hedonism for a couple of nights but the fashionable nightlife is not all the island boasts. For a more authentic experience, hire a car on the island and spend a day discovering some almost untouched coves and unspoilt beaches or set sail for nearby Delos Island, one of the most important mythological, historical, and archaeological sites in Greece.

Matt Fisher

Matt Fisher


There is no place like the Cycladic islands for soaking up the slow pace of Greek life, whether it be lying on a deserted beach or sipping on wine at a local taverna with only the buzzing cicadas to disturb your reverie.


Any lingering pre-holiday stress will slip away as the ferry docks at the island of Naxos. Halcyon days –  a minimum of five would be our recommendation –  await at one of the most beautiful islands of the Cyclades, where sandy beaches and calm waters are complemented by an interior of Venetian castles and traditional villages perched on mountain cliffs.

Chora, Naxos’s capital town, is a lively and fun place to be and the remains of Portara, the ancient temple dedicated to god Apollo, provide archaeological interest. Overlooking the town is the Venetian influenced castle called Kastropoliteia, the palace of the conqueror Marcos Sanoudos. Visit at sunset, just after your late afternoon swim, before meandering the narrow, bougainvillea clad alleys in search of that perfect blue tabled taverna.

When it comes to beaches Naxos is blessed but our favourites are sheltered Agios Prokopis and Agia Anna, a paradise for wind surfers and water sport lovers. But there are others. Hire a car and go in search of your own slice of paradise or let us arrange a private boat trip to the Little Cyclades – now they are off the beaten track.

Inland, Naxos has dozens of villages to explore including Apiranthos, Filoti and mountainous Halki, with its well-preserved mansions along have I travelled back in time streets. And it is in this mountainous area food lovers will unearth the traditional cuisine of the island such as Patoudo, a local lamb specialty seasoned with local herbs such as white beets, fennel, garlic and olive oil.


Final port of call is Santorini, the volcanic island with arguably the finest sunset you’ll ever witness.. Yes this is a big statement but go and you’ll see what we mean. Such a claim to fame does certainly draw the crowds, particularly to cliff hugging Oia village where it’s not unusual to find the audience clapping as the sun slides slowly into the Aegean. But there is more to Santorini than its postcard views.

Akrotiri is one of the most important prehistoric settlements of the Aegean and you can taste an excellent drop at one of the islands local wineries. Santorini took its present form following an epic volcanic explosion thousands of years ago, which left behind the striking Caldera you see today, and you can experience the true magnitude of this dramatic landscape on a private catamaran cruise. Sail the waters of the Caldera, exploring hot springs and private bays, where you can swim or snorkel the inviting waters.