...Trip idea

Greek Island Hopping in the Cyclades

This two week island hopping 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.


  • 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-track 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.

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 or private yacht, taking in the shimmering Aegean Sea panorama as your next destination emerges on the horizon.

How to Get There:

Ferries and hydrofoils to the Cyclades 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.

Combine With:

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

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.

Acropolis, Athens, Greece
Theatre of Dionysus below the Acropolis in Athens, Greece
Mykonos island in Greece Cyclades
Mykonos, Greece – Traditional whitewashed street of Mykonos town

Athens & Mykonos

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 – and 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 and you can also fly. Referred to as the St Tropez of the Aegean, the island boasts beaches with powdery white sand, chic bars, elegant restaurants and lively nightlife. Give in to some swanky hedonism for a couple of nights but for a more authentic experience, hire a car or driver 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.

Naxos, Cyclades, Greece
Naxos, Greece
giardini naxos town
Naxos, Cyclades, Greece


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. Meander the narrow, bougainvillea-clad alleys in search of that perfect blue-tabled taverna.

When it comes to beaches Naxos is blessed, our favourites are sheltered Agios Prokopis and Agia Anna or explore lesser-known Little Cyclades by private boat trip. Inland, Naxos has dozens of villages to explore including Apiranthos, Filoti and mountainous Halki, with its well-preserved mansions, lost-in-time streets and rustic tavernas serving patoudo, a local lamb speciality.

Beautiful Oia town on Santorini island, Greece
Beautiful santorini landscape
Santorini, Greece. Picturesq view of traditional cycladic Santor
Omma, Santorini, Greece


Final port of call is Santorini, the volcanic island with arguably the finest sunset you’ll ever witness. 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 island’s 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.

Sifnos, Cyclades, Greece
Sifnos, Cyclades, Greece
Traditional Greek village, Tinos island

Where Next?

Instead of heading home, continue your Cyclades Island hopping adventure on one of the lesser-explored islands such as tiny Tinos, foodie Folegandros or stunning Sifnos. Talk to us about custom-fitting your itinerary to fit in all your favourite things whether that’s a luxe villa, characterful hotel, cookery classes, yacht charters or ancient ruin tours.

Folegandros, Cyclades, Greece

Have questions? Our knowledgeable team of experts are on-hand to take your call or if you prefer by Zoom. Talk to us about your holiday dreams or challenge us with your travel conundrums.

Get in touch

Keep Browsing

Enjoy reading our colourful collection of travel blogs, insider journeys and first-person insights. Our articles are designed to fuel your wanderlust. Feeling inspired? Give us a call and our experts can start planning your next travel experience.

Trip idea
A Rail of Three Cities…in Italy

Sit back and enjoy the ride with cultural stops in Venice, Florence and Rome, private transfers between cities and stations and some of Italy’s finest hotels to relax in.

Booking with Bailey Robinson means access to the finest travel experiences. When planning your holiday we do all the hard work – in-depth research and meticulous organisation. You can be confident in the individual care for your holiday from your dedicated and experienced Personal Travel Designer and Concierge.
Just back from
Ikos Dassia, Corfu – Greece
Ikos Dassia, Corfu
Trip idea
Croatia in Style
Travel Ideas