How to Do a Cyclades Island Hopping Trip (Greece)

Blue shutters, white walls, boundless stretches of sand – the Greek islands have always been a dream destination for me. Among these offshore treasures are the famous Cyclades Islands, tempting you with breathtaking views and rich heritage sites. With all of these atmospheric wonders, why not spend your lockdown planning a Cyclades Island hopping trip. 

I did it a few years ago and travelled around Mykonos, Santorini and Ios, but now I’m tempted by the smaller islands and would love to go back to see more on a Cyclades Island hopping trip with friends. Here’s how to do it…

Where are the Cyclades Islands? 

In short: Greece.

Nestled offshore of mainland Greece, the Cyclades Islands are a cluster in the Aegean Sea. Visitors can reach these impressive getaways via boat or flight; there’s no bridge by land. Domestic flights connect Athens and Thessaloniki to the busy airports of Santorini and Mykonos, and a slightly less travelled Paros airport. 

Best ones for a Cyclades island hopping trip?

There are 18 Cyclades Islands, but you’ll be hopping quite a bit if you try and fit all these in! Plan for quality time at carefully chosen islands instead; let’s look at the 5 most popular Cyclades Islands on the list.

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1. Mykonos

Mykonos is all about Greek glamour and future-meets-past. Natural wonders are guaranteed of course, but it’s more accurate to describe it as ‘don’t sleep, just party’. It’s where people go to tan and spend, to forget about the world beyond their Greek summer. 

Mykonos is well known for the seamless blend of blaring, thumping music and the weathered white-painted exteriors of the night-scene. Hora (a.k.a Mykonos Town) features parades of cool kids – elegantly-dressed with cocktails in hand and bikinis for evening wear. Other holidaymakers retire to luxurious resorts as Paradise and Super Paradise Beach transform into a stage for world-renowned DJs. Tourists here hire Mykonos villas to really get into the swing of the island.

Still, in quieter seasons or in the hottest hours of the day, you can find peace at the 16th-century windmills atop the hill. Bask on the beaches of Kapari, Paraga and Agios Sostis without the drunken revelry. Indulge in authentic Greek cuisine or delve into the Archaeological Museum of Mykonos for more cultural richness. Tourliani Monastery and Panagia Paraportiani are glimpses of another personality. I spent two days in Mykonos and loved hiring an ATV and driving up to the vineyards.

Have time to spare? Detour to nearby Delos for an archeological adventure. Mykonos is about duality and I’m all for it.

One other thing to note about Mykonos, for your Cyclades island hopping adventure, is that it’s pretty blummin expensive. Be warned!

2. Santorini 

Santorini – sundrenched and airy, it’s a well-known name for any travel enthusiast. I used to pore over photos of its white-washed houses and winding steps, dreaming of an all-blue stay. After all, there aren’t many places where towns are built into cliffsides!

Santorini really is a magical place to visit – check out my pics.

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The unusual landscape is the result of a 16th century volcanic eruption, where the principal towns of Fira and Oia later developed on the island’s slanted, rugged remains. As you can imagine, the views from the caldera rim overlook the generous expanse of the Aegean Sea. Below the calm surface is an underwater crater for divers to explore and marvel at.

Santorini’s natural attractions also extend to its unusual beaches. Instead of the usual caramel-colored strips, you’ll come across black, red and white lava-induced sand. It’s not just nature either; the path that connects all of Santorini’s villages are lined with terrace restaurants and boutique shops – a great place to pick up some Greek souvenirs. Charming backstreets lead into vineyards and wine caverns, glassware and handicrafts on display.

Whether you alight for an overnight stay or simply sail up close for a glimpse of this iconic island, try to time your visit to overlap with sunset – the dusky glow between Oia and Thirasiá is spellbinding. 

3. Paros 

Like its sibling islands, Paros is a vision of white and blue. Easily accessible via Athens and Thessaloniki by ferry, it’s an easy introduction to Greece’s classic charms: sea front residences, beaches gently corralled by waves and plenty of dreamy scenery. 

Paros has strong Byzantine roots; visit the Byzantine Museum to learn about the island’s rich history. The hand-crafted iconostases and ancient heirlooms are impressive, although what entranced me most is the hilltop Venetian Castle. The 6th century Katapoliani Church is another historical landmark with plenty of secrets – try to find its hidden gate!

Cyclades island hopping

There’s no end to piquant villages either. Capital Parikia is a great starting point, showing off a wildfire of elegant and white mansions. Wander into quieter neighborhoods for brilliant bursts of color as flowers form canopies over houses. The traditional villages of Naoussa, Lefkes and Marpissa are stunning, hosting a Venetian fortress, folk culture museum and monastery respectively.

For an endless supply of sun, cruise past olive groves to find the beaches of Logaras and Pisso Livadi. The wild rock formations of Kolymbithres beach are perfect for dramatic photoshoots, whereas Kalogeros is all about adventure with a natural spa of red and green clay pools. 


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4. Naxos

If you want to make the most of your Cyclades Islands trip, why wouldn’t you want to stop at the largest island of the group? From the stone ‘gate’ standing sentinel to staunch Mt. Zeus, Naxos is the sampler plate of Greek-Venetian treasures. 

Classic Greece, Byzantium, Venetian and Frankish influences can be seen everywhere. The Temple of Apollo is a fitting tribute to ancient myths; Panagia Drosiani, one of Greece’s most revered churches, shares the tale of secret religious lessons in cave-like chapels during the Turkish occupation. Other historical sources include Della Rocca-Barozzi Venetian Museum, the Temple of Demeter and marble quarries. Even the fortified waterfront mansions reveal much about centuries of Venetian rule.

Cyclades island hopping

What makes Naxos so lovely however is the fertile land hidden within the mountains. Not only is Mt. Zeus the highest peak in the Cyclades, the tropical climate up top mean green wealth! Olives, grapes, figs and other citrus fruit decorate the spaces between pretty villages, like charming Halki and Apiranthos. I suggest hiking through the lush plantations or along the coast.

Naxos is a top holiday location for its diverse landscapes and material attractions. 

5. Syros 

Lovely Syros is the middle ground between Naxos and Santorini, mixing those famous white houses with colorful mansions leftover from Venetian rule. Quiet and calm, it’s not too far off from Athens either; challenge those 78 nautical miles in the day and moor before sunset. Surprisingly, this small island is the capital of the Cyclades! Because it doesn’t rely on tourism to function, there’s less pomp and more local living to experience.

Cyclades island hopping

The town of Ermoupoli is arguably one of the grandest in the archipelago, filled to the brim with interesting buildings. St. George’s Cathedral, the Church of the Dormition, Ermoupoli Industrial Museum and St. Nicholas’ Church are a few that stand out. For some fascinating historical digs, visit Syros Archaeological Museum and Apollon Theatre. 

One of the best things to do is simply to walk around – the villas flow down Ermoupoli hill in pastel-hued waves, broken only by the silhouette of the Town Hall. You’ll absolutely love the cafés along Plateia Miaouli, while the narrow streets and marble steps lead you into view points with panoramic views.

Find your way towards Galissas Beach too; a sheltered cove with homemade Greek food for the taking. Before you head off to sleep, Syros’ cuisine will spoil you with fresh seafood and loaded salads. 

Best Cyclades island hopping route suggestion

Fly into Santorini and kick-start your Cyclades Island Hopping adventure with the postcard representation of Greek islands. Since it’s the furthest from Athens, start the on-water leg of your trip for when you’re within the island clusters. Next up is Naxos, the perfect blend of history, modern town and nature – neighbouring Paros will follow up with more historical riches.

Once you’ve had your fill of history, move over to Mykonos for a night of partying. Finally, with your energy running low, recharge at serene Syros. 

Cyclades island hopping

Alternatively, if you have the means to rent a yacht, embarking on an all-sail trip can challenge a long run from Athens to Syros. After resting from the day-long journey, choose between Paros and Mykonos for your second island stay. Naxos slides neatly into the fourth island slot, letting you enjoy either a tour around town or into the mountains. Round off with Santorini’s spectacular views and fly back to Athens. 

More tips for your Cyclades island hopping trip

You definitely want to be well-prepared! Remember to bring along:

  • Beach towels; or purchase light-weight Turkish towels that are easy to roll and pack
  • Backpacks for daily necessities
  • Hat and sunscreen!
  • Beach cover up for windy days
Cyclades island hopping

You’ll also find that ferries are your saving grace!

  • Book ferry tickets and transfers in advance, especially if you’re travelling during peak seasons. Book through reliable services like Greeka or Note that there’s no singular ferry pass every island has different ferry companies. 
  • Ferries are always late so check your ferry before heading to the port. 
  • While ferries have luggage areas for easy storage, make sure you have distinctive tags and luggage locks as people tend to pile their bags without order.

When it comes to money:

  • Tipping isn’t common but do round up your bill to a convenient round number.
  • The islands take small bills over big ones; most meals average 10 euros so they may not have change for 50 euro notes.

A final note about water:

  • Don’t waste! The Cyclades experience water shortage so limit your showers and reuse towels.
  • Buy bottled water; tap water isn’t safe to drink.
  • Hydrate all the time – the heat will get to you!


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