Island-Hopping in the Cyclades, Greece

Paraportiani church in Mykonos Town in the cyclades in Greece

Let me show you why island-hopping in the Cyclades is the best way to experience these gorgeous Greek islands.

The islands of the Cyclades, sprinkled across the Aegean sea in Greece, are some of the most delightful in the world. I wouldn’t hesitate to recommend island-hopping in the Cyclades to anyone. Well… Maybe not those who get really seasick… Because the best way to explore the Cyclades is definitely by boat.

I spent some time island-hopping in the Cyclades on a small ship tour, and I loved getting to know these stunning islands. In this article, I will share my highlights from the Cyclades.

Disclosure: This article contains affiliate links. These are links to products or experiences I recommend and if you were to buy something after clicking on them, I might earn a small commission at no extra cost to you. Any earnings go towards the upkeep of this blog, which I appreciate.

Why Go Island-Hopping In The Cyclades?

There’s nowhere on earth like the Cyclades islands in Greece. Each island has its own unique character and appeal, but all of them share a special charm unique to the Cyclades. The islands themselves rise from the blue Aegean like proud, rocky monuments. And the towns… The towns are special. The white-washed buildings, neatly paved pathways and stunning bougainvillaea flowers of the Cyclades worked their magic on me immediately.

white-washed Greek house with orange blossoms and green doors and shutters
Classic Cyclades style

Highlights of Island-Hopping In The Cyclades

I had the privilege of visiting some of the best islands in the Cyclades, read on for inspiration about which ones to visit.

1. Folegandros – The Most Peaceful Island

I hadn’t heard of Folegandros before I visited – and I am surprised it isn’t better known, because it is really gorgeous. But equally, I hope it doesn’t get more famous, because one of the things I liked about it is how peaceful it is. It ‘s a calm, quiet Greek island.

We didn’t have time to experience all the things to do in Folegandros, but we really loved the time we had there. We docked at the harbour town of Karavostasis, which is a tiny sprinkling of white houses, some fishing boats and a ferry terminal.  From there, we caught a bus to the main town of Folegandros, which sits on a cliff edge overlooking the dreamy Aegean.  The views are breathtaking!

Viewpoint on Folegandros overlooking cliffs and the blue aegean sea
Stunning views from Folegandros Town

The town is also incredibly pretty: like all islands in the Cyclades, the houses and churches are white-washed, the doors and windows painted from a palette of pastels, and the pathways are paved with grey stones and white trim.  Picture-perfect.

White washed Greek church with domed roof and cross in Folegandros in the Cyclades
Perfect Greek Church

We marvelled at the view from the cliff, wandered the streets for a while, then ate a quiet dinner outside in one of the squares under a blossoming tree – it was absolutely divine. After dinner, we caught the Folegandros bus back to the port to fall asleep in our boat.

2. Santorini – The Most Spectacular Island

Any Cyclades island-hopping itinerary should include Santorini. Before I went, I had long dreamed about going to Santorini, and it didn’t disappoint!

What captured my imagination about Santorini is its geography.  It is basically a volcano.  There was a massive cataclysmic explosion around 1610 BC – one of the largest volcanic eruptions in recorded history.  This eruption created a huge caldera, which flooded – and this is the circular ring of islands we see today. Since then, in the middle has sprung new, much younger volcanic islands called Palea Kameni and Nea Kameni, which last erupted in 1950.

View of santorini's caldera from the town of Oia
View of the Caldera from Oia

The towns of Fira and Oia are on the main island and they perch on the steep clifftop, overlooking the caldera and the new volcano.  The views are dramatic.

Some people complain about the crowds and the prices at Santorini because it is such a popular destination, so you might be wondering, is Santorini worth it? 

Well, when I went, it was very crowded and expensive (and hot!) – but for me, those views were worth the hassle and the cost. There are lots of things to do on Santorini, including a catmaran cruise around the caldera, but we spent most of our time going from bar to bar to stay cool and calm while enjoying the views from various vantage points.  I couldn’t get enough of it!

But if you want to go when it is quieter and cheaper, consider visiting Santorini in winter.

Sunset over the Islands of Santorini in the Cyclades
Santorini Sunset

Top tip: Santorini is one of the best places in the world to watch the sunset – but to get a good spot from which to watch it you need to book in advance because restaurants with views can be busy.  Alternatively, go to a bar and order bar food rather than have a sit-down meal in a restaurant and go early (late afternoon or early evening, before the crowds arrive).  You might find it easier to get a seat with a view this way.

Fun fact: although it is currently dormant, Santorini is one of the Decade Volcanoes, a group of 16 volcanoes monitored by the International Association of Volcanology and Chemistry of the Earth’s Interior (IAVCEI) because of their history of large, destructive eruptions and proximity to populated areas.

If you have a few days to spare, consider this Santorini itinerary for 4 days.

3. Paros – The Quietest Island

Paros is a fairly big island, and we explored two of its towns while we were there: the main harbour town of Parikia and also Naoussa, on the north coast.

Row of white houses on the shore of Naousa Town on the island of Paros
Naousa on Paros

Both were as pretty as any Cycladic town, but I especially liked Naousa because it seemed very modest and, like Folegandros, not overly touristy. We clambered over some rocks to get to Piperi beach, then wandered back into town for a drink. It was so quiet and calm – it felt like we had the place to ourselves. If we’d had more time, I would have liked to hire a small boat and explore the island coastline ourselves.

I loved watching the turquoise waves crash on the rock, right next to our bar.

4. Mykonos – The Most Glamorous Island

Mykonos is known as a glamorous and gay-friendly party island, and features on many Cyclades island-hopping itineraries. My first impressions were that it was picture perfect, not quite real – it felt like we were wandering around a movie set!

paved streets of Mykonos with white houses. blue shutters and pink bougainvillea
Picture Perfect Mykonos

It is also much more high-end than the other islands in the Cyclades.  As we walked the spotless and pretty streets of Mykonos Town, we kept coming across luxury brands, like Louis Vuitton, Gucci and Chanel, which I hadn’t expected!  I didn’t come to the Greek islands to shop, and even if I had, I would not have been able to afford those brands – but that’s OK because Mykonos has other charms.

There are lots of lovely things to do in Mykonos – it’s one of the best islands with beaches in Europe.

I just loved the pure white and irregular shape of the Paraportiani Church near the harbour.  Be warned, it is a top selfie location, so you may have to wait a while to get a shot without anyone else in it.

Paraportiani church in Mykonos Town in Greece
Paraportiani Church

I also enjoyed getting a drink from one of the bars on the shore with a view of Little Venice, a strip of old houses built right up to the water’s edge. Some people take a sunset cruise around Little Venice.

And in the evening, I found an open-air cinema. We watched a movie under the stars. The movie wasn’t that good, but it was a warm night, the cocktails were great, and the stars were out – so overall, it was pretty magical.   

5. Delos – The Most Ancient Island

From Mykonos, you can take a boat trip to nearby Delos Island.

It is a Unesco World Heritage site because of its historical and archaeological significance. Greek mythology says it is the birthplace of Apollo and Artemis, and it was a significant place for worshippers of them.  It was also a major trading centre for the Roman Empire. It was inhabited between the 3rd millennium BC and the 7th century AD.  

Sunset behind the ancient remains on the island of Delos
Sunset on Delos

You can’t stay on the island (only a handful of people live there now), but you can explore the extensive ruins.  Some statues and artefacts are housed inside a museum, but you can also walk the remains of the city, including a theatre, lots of temples and houses, with some nice examples of decorative tiled floors and walls.

Top tip: go towards the end of the day. As the sun sets, the stones glow a gorgeous golden colour. It is glorious.

6. Syros – The Smartest Island

Syros island is kind of in the middle of the Cyclades islands, and its main town, Ermoupoli, is the Capital of the region.

Street scene in Ermoupoli on Syros in the cyclades
Ermoupoli, Syros

Named for the Greek god, Hermes, Ermoupoli has a different feel to the other Cycladic towns. Where they have that small, town white-wash feel, Ermoupoli is bigger, grander. Its buildings are neo-classical in style; its streets wider and smarter.

It is still gorgeous though: there are plenty of things to do in Syros but I enjoyed wandering the marble streets and choosing from the many restaurants.

7. Kythnos – The Best Beach

The last stop on my Cyclades island-hopping route was Kythnos, which is a mountainous island fairly close to the mainland and Athens.

The highlight here was definitely Kolona beach, in the northwest of the island.  It is a double beach – a strip of sand connecting the main island to the tiny islet of Agios Loukas.

Yachts in the bay near Kolona beach on Kythnos island in the late afternoon
Kolona beach, Kythnos

There’s not much infrastructure there – just a church and a café, so not many places to take shade from the sun.  But it is a magnet for yachts and small ships like the one I was on.  I kayaked out to the beach and swam back to the boat (my husband took the kayak back).  And then from our boat, we watch the sun go down over Kythnos Beach (which you can also do via a Sunset Cruise).

It was wonderful – the perfect way to say goodbye to the Aegean before we made our way back to Athens.

Map Of The Cyclades Islands

Here’s a map showing the islands I recommend in the Cyclades, plus the international airports in the area:

How To Use This Map: Click the tab in the top left-hand corner of the map to view the layers. If you click the icons on the map, you can get more information about each one.  If you click the star next to the map’s title, it will be added to your Google Maps account. To view it on your phone or computer, open Google Maps, click the menu, go to ‘Your Places’ or ‘Saved’, then click Maps and you will see this map in your list.

When to visit the Cyclades

The weather in the Cyclades will be great from May all through the summer – but I recommend waiting until September or October for three reasons. One, it won’t be as blisteringly hot as June, July & August, but it will still be lovely and warm.  Two, it won’t be as busy because most children are back at school in September, so families tend not to take holidays then.  Three, prices will be slightly lower as it is the shoulder season.

For these reasons, the Cyclades are among the best warm places in Europe in October (and Autumn in general).

How To Get To The Cyclades

Some of the islands have international airports, including Santorini, Paros and Mykonos. Another option is to fly into Athens and catch a ferry to the islands from there. If you catch a fast ferry, even one of the longest journies, from Athens to Folegandros, takes only 3 hours 45 minutes.

Use Skyscanner to check the best flight deals and Direct Ferries for ferry schedules.

Or you can do what I did and take an organised tour of the islands! 

Small Ship Island-Hopping Tour

I wasn’t keen on the idea of a huge cruise ship, and couldn’t afford to charter my own boat (which would be my preference if I was rich enough!), so I booked my husband and me on a small ship tour from Seafarer Cruises on the Jewels of the Cyclades route, departing from Athens. I don’t have any deal with them – but I did enjoy my island-hopping Cyclades cruise, so I’m happy to share the details. 

View from a boat of the sea and an island in the cyclades
View from the boat

Accommodation On The Ship

The boat I was on was 48m and had 25 cabins, to accommodate a max of 50 passengers. We had a ‘category B’ room. These are a little cheaper because they are below deck. The room was small and dark, with only a small porthole for light and a tiny en suite bathroom. However, we weren’t planning to spend much time in it, so we didn’t mind! The hardest part for me, as an extreme introvert, was finding spots on the boat I could have time to myself.

Sailing in the Cyclades

During my island-hopping Cyclades adventure on the small ship, most of the long sailing distances were done at night. For example, we went to sleep in the harbour of Karavostasis on Folegandros, and woke up in the caldera of Santorini. This was different to my sailing holiday in Croatia, where we sailed during the daytime. In some ways, this was a disappointment, as I do love to gaze at the scenery as we sail, but it meant we had more time on each of the islands, which was great.

One of my favourite things about island-hopping in the Cyclades on a cruise rather than organising my own ferries etc is that we had regular swim stops.  I love swimming and there are so many gorgeous spots we could pull in and swim in between islands. 

Turquoise water in a rocky cove in the Cyclades Islands
One of the gorgeous swim stops on our island-hopping Cyclades tour

The Last Word

What about you?  Have you been island-hopping in the Cyclades before? Are there any other islands in the Cyclades you recommend? Or any other Greek islands anywhere else? 

Have you ever taken a small ship tour and would you recommend it? I’d love to hear from you!

And if you need more inspiration for Greece, check out my two-day itinerary for exploring Athens.

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6 thoughts on “Island-Hopping in the Cyclades, Greece”

  1. Brenda & Stu | Passports, Planes & Postcards

    This sounds amazing!! I would love to go island hopping one day, even if I suffer from motion sickness – I’ll just make sure to have plenty of travel sickness tablets with me!!

  2. I have done cruising in large ships, but never on a small boat. It certainly would appeal to me, my main concern would be getting seasick. I have been to Santorine and Mykonos on a cruise and would love to go back for a longer stay. We are planning to explore Greece by motorhome next year, but not sure if we will visit the Cyclades. Just discovered your blog, you have some great articles 😀

    1. Thanks Gilda! I didn’t experience any travel sickness on the small ship, though I did experience mal de debarquement after we left the ship! I’d like to go back to Santorini for longer also. The downside of island-hopping the way I did it is that you don’t get long in any one place – but you do get to experience many wonderful places 🙂

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