3 minute read by Island HoppingLast updated 19th Jul 2023

The Ultimate Guide to Cyclades Island Hopping

Mykonos, Santorini, Naxos, Ios – the Cyclades islands contain some of the most iconic destinations in the Mediterranean. If we had to pick a part of the country for first-time visitors after a quintessential Greek experience, this would unquestionably be it! We're talking whitewashed villages on dusty hills, sun-baked beaches crowded by gnarled olive trees, mountains of sage and thyme, tavernas that serve lemon-doused fish cuts under bougainvillea – travel brochure stuff. This ultimate guide to Cyclades island hopping will delve into the very heart of this famous region. It will showcase some of the must-see spots that speckle the azure middle of the Aegean Sea and offer some tips on popular ways to move between them. We'll also reveal the best times to travel to the Cyclades islands, no matter if you're after heady summertime party days on Mykonos or September beach-hunting sessions on Milos.

What's in this guide to Cyclades island hopping?

  • Where are the Cyclades islands?
  • When to visit the Cyclades?
  • A guide to the top Cyclades islands
  • Popular island-hopping routes around the Cyclades
  • How to get around the Cyclades islands

Where are the Cyclades islands, exactly?

The Cyclades islands stretch from the very end of the Attica Peninsula (the home of Athens) into the depths of the Aegean Sea. They sort of bridge the gap between mainland Greece and Crete, running north to south in a paint-brush splatter (white paint, of course). The northernmost of the isles is Andros, closely followed by Kea, which sits just a stone's throw from the ports on the eastern side of the capital. Furthest south is Santorini, a rugged island and onetime volcano, washed by the waves a mere 300 miles from the coast of North Africa.

When to visit the Cyclades

The Cyclades islands follow a very clear seasonal pattern. Scorching in summer, warm in spring and autumn, and chilly with breezes in winter, it shouldn't be too hard to decipher when most of the crowds come. But we think every season has its draws…

The Cyclades in winter

Many of the Cyclades islands survive on tourism. That means things often go into hibernation during the winter – tavernas stop serving, hotels close. Your best bet is to choose one of the lived-in, local isles. Places like Kea and Tinos are great options. It might be chilly, though. Even Santorini, the southernmost of the Cyclades, sees daily averages of 15 C in December. Inter-island ferries can also stop for the winter, making it hard to plan Cyclades island hopping trips.

Best Cyclades islands to visit in winter: Andros, Tinos, Kea.

The Cyclades in spring

Spring comes early to the Cyclades. The water starts warming around late March, with temperature averages going from about 16 C to 22 C between then and May (again, that's in Santorini, so expect it to be a touch chillier in northern isles like Andros). Rains really drop away by late spring, to the point where you can expect an average of three days of rain in 30. The best part? Crowds haven't really cottoned on yet, so beach hunters and hikers will find sands and trails pretty empty.

Best Cyclades islands to visit in spring: Naxos, Milos, Paros.

The Cyclades in summer

Summer is a dream in the Cyclades islands. Hardly a raindrop in sight and daily temperatures between 27-32 C make it the season of holidaymaking. Of course, an uptick in mercury is matched by an uptick in crowds. That's not always bad, because it means the buzzy party hubs of Mykonos and Ios will be swinging like it's nobody's business. Santorini, though, can be heaving (not to mention prohibitively expensive). Either way, this is by far the most popular time to hit the region.

Best Cyclades islands to visit in summer: Mykonos, Ios, Naxos.

The Cyclades in autumn

Autumn might just be our overall favourite time in this balmy corner of Europe. The strong summer Meltemi winds can cool a little, while thermometers still read around 20-25 degrees well into October. What's more, the seas are at their warmest, hitting a peak of about 22 (AKA half a hot tub) in early September. We love that the islands seem to turn a rich colour palette of ochres and oranges in the autumn, while harvest brings fresh walnuts, mountain herbs, and olive oil to the tavernas. Crowds are a fraction of what they were only a month before, too.

Best Cyclades islands to visit in autumn: Santorini, Folegandros, Anafi

The Cyclades islands

There are 220 members of the Cyclades chain in all. That makes this the biggest archipelago in the Greek seas. We won't go on about them all, just a few that we think stand out from the crowd; the ones that give us shivers as they appear on the horizon during island-hopping adventures…


Santorini is probably the most famous location in Greece. Move over Acropolis, this is a collapsed volcano rising straight from the Aegean Sea. It's got ancient history, stunning whitewashed towns that drape over the cliffs, luxurious cave hotels – what more could you want? Santorini is the perfect place for bucket-list yachting days and romantic honeymoons alike.


Mykonos is the sort of island that will charm you into staying way longer than you wanted (or can afford!). The south-west coast is a tiara of buzzing resorts – Psarrou, Super Paradise, Paradise. These are places with the chicest beach clubs out there, and stunning runs of sand and turquoise sea to back them up. Later on, enjoy a sunset at the Mykonos Windmills and then head to Little Venice to keep the party going.


The party basically never stops on Ios in the summer. From May to September, it's one big blowout of cocktails, EDM, sunset shows, and dancing to dawn. The main Chora is the place to be, with mega clubs and shot bars like Slammers (try the in-house Slammer shot but protect your head!). During the day, hangover permitting, why not scout out the east coast beaches? They're paradisiacal coves where there's often not another soul in sight.


Paros is much more than just a place to hop on and hop off ferries, though it is the travel hub of the Cyclades. Head north to find the charming village of Naoussa, with its centuries-old fishing folk cottages and crooked stone alleys. The tavernas there are excellent if you like seafood, but don't linger too long because there are old Byzantine villages in the mountains and empty coves on the east coast for lazing and snorkelling. A trip across to Antiparos, a charming, rustic neighbouring island, is a great way to slow down the pace even more.


Naxos offers a hit of two of the Cyclades's top draws: Beaches and backcountry. The vibrant port marina soon gives way to scintillating sands that roll out southwards, first with lively Plaka, then to the charming, church-topped Aliko Agios Georgios, then to so-called Hawaii Beach (named for its cling-film-clear waters). Inland, you can hit the trails of Mount Zas to trek cypress woods to long-lost monasteries.


Folegandros is a true charmer; a place that's fast becoming a very popular pitstop on Cyclades island hopping tours. Neatly placed between Milos and Santorini, it rises to 455 metres up in a series of precipitous ridges of volcanic rock. The main draw is the Orthodox Church of Panagia, where pretty much everyone on the island goes for the sunset. Afterwards, descend to Chora for mezze dinners on the plazas.


Beach lovers cannot miss Milos. This one's got arguably the most striking coastline in the whole of the Cyclades chain. In the north, it bends into the whittled bays of Sarakiniko, where the headlands look like ancient Greek statues. In the south, it turns to sea stacks and cavernous grottoes at the Kleftiko rocks. Be sure to head out on a boat trip, and don't miss the catacombs and amphitheatre by the main village.

Popular island-hopping routes around the Cyclades

There are gazillions of ways you can organize your Cyclades island hopping. Most of the major islands are linked by very regular ferries, while bijou taxi boats connect up the smaller specks on the map. The hardest part is probably going to be laying down that itinerary in the first place. Here are just a few suggestions:

  • The bucket-list route: Santorini-Ios-Paros-Mykonos – Do this if you've not been to the Cyclades islands before. It takes in the major islands and reveals the core attractions of the region, including Santorini's soaring caldera, the Mykonos sunset clubs, and the shimmering beaches of Paros.
  • The party route: Mykonos-Paros-Ios – Calling all hedonists, this itinerary focuses solely on the islands where it's normal to wake up after 12am and sizzle off the hangover on the shoreline. Mykonos is the most stylish of the lot, while Paros is for local brewpubs and tavernas, and Ios (the finale) is where it gets truly wild.
  • The off-the-beaten-track-route: Serifos-Milos-Folegandros-Sikinos – A trail through the northern and western Cyclades islands that showcases some of the lesser-known destinations. You'll get to see the time-forgotten hamlets of Serifos and the sunset from the church on Folegandros.
  • The beach lover's route: Naxos-Paros-Ios-Milos – The Greek coast takes centre stage here. Naxos offers white-sand bays tinged with a touch of pink and yellow south of its main port (just Google Hawaii Beach Naxos!). Then comes Ios, which is known for partying but has spectacular east-coast coves. Finally, it's Milos, where the white-marble shores are sure to take the breath away.

How to get around the Cyclades islands

Every Cyclades island hopping trip needs some form of transport. Thankfully, you've got a few options when you come to plan your odyssey from Santorini's cave hotels to the wild hills of Kea. Let's take a look…

Ferries in the Cyclades islands

Ferries are by far the most efficient way to travel. We'd recommend them as the go-to mode of transport on any Cyclades island hopping trip. From spring to autumn, you can expect a very comprehensive schedule of boats, and it's rare not to find a way to get from A to B in a day or two. The island of Paros acts as a sort of nerve centre for all the boats in the Cyclades, so you might find that's a good place to begin. Oh, and book those tickets early. Or, better yet, bag yourself an island-hopping trip that includes tickets. Securing seats on popular routes at the last minute can be a nightmare.

Flights in the Cyclades islands

There are really only two airports in the Cyclades islands: The Santorini National Airport and Mykonos International Airport. The first is better for accessing the southern Cyclades (Milos, Ios, Folegandros), while the latter is better for hitting the northern Cyclades (Tinos, Paros, Naxos). Both are mainly served by seasonal flights, including low-cost connections to London and other major European hubs (check out Ryanair and easyJet for the best deals). You can also find domestic links to the airport in Athens with national flag carrier Aegean Airlines.

Private yacht charters in the Cyclades

Talk about bucket-list experiences – a private yacht charter to take you through the Cyclades islands has to be up there with the Trans-Siberian or seeing the Northern Lights. This is the mode of transport that offers the most freedom. Fancy a Mykonos party? Just raise the sail. Want to seek out a secret cove on Antiparos? Pull up the anchor. Of course, you'll need a skipper's license if you want to pilot the boat yourself, and charters don't come cheap. That's why we'd say stick with the public ferries if you only want to see a handful of places on your trip.

We sincerely hope that this guide to Cyclades island hopping has got you pining for your Ios party nights and Santorini caldera views. If so, be sure to get in touch for more information on our Greek island-hopping trips.

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